著者

春沢 信哉 栗原 拓史

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.53, no.8, pp.712-723, 1995-08-01 (Released:2009-11-16)

参考文献数

36

被引用文献数

4 5

---

A highly stereoselective synthesis of (Z) - or (E) -double bonds in 10-membered thiolcarbonates is achieved by the [3, 3] sigmatropic rearrangement of 8-membered thionocarbonates which proceeds through the chairlike vs. boatlike transition states. The formation of the 8-membered intermediates followed by their [3, 3] sigmatropic rearrangements were investigated by experiments and theoretical calculations. Their utilities of this methodology have been demonstrated by the unique and stereoselective synthesis of (-)-yellow scale pheromone. Moreover, medium-membered heterocyclic allenes were synthesized by this method. The structure and reactivity of a new type of strained 8-membered allene were also examined. Using this method combined with a novel application of the newly developed SmI2-HMPA reduction of the cyclic allene, the antifungal constituent of a Sapium japonicum was synthesized.

著者

徳山 英利 中村 正治

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.63, no.5, pp.523-538, 2005-05-01 (Released:2009-11-13)

参考文献数

102

被引用文献数

16 20

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Among non-conventional stimulations to accelerate organic reactions, high-pressure, ultrasound irradiation, and microwave irradiation are representative methods and are now becoming more and more popular in laboratories. This review focuses on organic reactions under microwave irradiation since this technique has attracted broad range of interest from the scientific and practical viewpoints. After the brief description on the historical and theoretical backgrounds of the dielectric heating, microwave effects, practical aspects of microwave heating (choice of solvent and microwave reactors), scope, and limitations of microwave-assisted synthetic reactions are discussed.

著者

Kei Gotot Takayuki Kawashima

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.63, no.11, pp.1157-1170, 2005-11-01 (Released:2009-11-13)

参考文献数

52

被引用文献数

6 6

---

Several kinds of bowl-type molecules were designed for regulation of the reactivities of the functional groups in their cavities, especially for kinetic stabilization of highly reactive species which have been difficult of access by conventional methods. The “peripheral steric protection” by these molecular cavities effectively prevents the bimolecular decomposition of the reactive species such as dimerization or self-condensation, and enabled the isolation of various species including a sulfenic acid, a selenenic acid, an S-nitrosothiol, and a Se-nitrososelenol, which have been known as important but elusive intermediates in biological reactions. Utilization of the molecular bowls as the ligands for transition metal complexes is also described.

著者

平林 一徳 森 敦紀

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.58, no.10, pp.926-933, 2000 (Released:2009-11-13)

参考文献数

35

被引用文献数

4 5

---

This article reviews organic chemistry of siloxane and silanol involving the preparative method as well as applications towards organic synthesis. Chapter 1 deals with the formation of siloxane bond and reactions of thus prepared siloxane compounds. Chapter 2 covers recent preparative methods for silanols and new synthetic reaction using silanol involving 1) utilization of silanol oxygen that serves as a base or a nucleophile, 2) transformation of neighboring functionality on the silicon substituent based on the interaction of silanol oxygen with an organometallic reagent, and 3) transformation of a carbon silicon bond of silanols directed to novel carbon-carbon bond forming reactions.

著者

河内 正治 難波 陸祐

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.42, no.9, pp.829-840, 1984-09-01 (Released:2009-11-13)

参考文献数

27

被引用文献数

1 3

---

Fluorine containing polymers have excellent characteristics such as superior heat resistance, chemical resistance, non-stick property, and various electrical properties, and they are widely used for chemical, electrical and mechanical applications.Nowadays eight kinds of fluorocarbon polymers and six kinds of fluoroelatomers are commercially available in the market.Not only are the high performance of fluorine containing polymers finding their continued applications, but also the functions of the polymers, such as the lowest refractive index or electron beam sensitiveness are attracting attention in new and unique applications. and many new fluorine containing polymers suitable for such new applications are being developed now.In this article, the characteristics and their applications are reviewed.

著者

稲本 直樹

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.26, no.7, pp.551-562, 1968-07-01 (Released:2009-11-13)

参考文献数

89

被引用文献数

1 1

著者

細矢 治夫

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.23, no.8, pp.660-673, 1965-08-01 (Released:2011-03-01)

参考文献数

47

著者

大橋 茂

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.19, no.1, pp.69-75, 1961-01-01 (Released:2010-10-20)

参考文献数

79

被引用文献数

1 2

著者

李 民雄 小林 幸夫 熊本 高信 白井 孝三

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.34, no.4, pp.228-231, 1976-04-01 (Released:2009-11-13)

参考文献数

5

被引用文献数

1 1

---

アミノグアニジン臭化水素酸塩と臭化シアンとの反応によりアミノグアニジンは4位の窒素がニトリル化され, これが直ちに加水分解された1-グアニルセミカルバジド臭化水素酸塩 (1), ならびにニトリル基にさらにアミノグアニジン塩が付加した直鎖状N1, N2-ジグアニジノグアニジン三臭化水素酸塩 (2) のいずれも新規化合物を得た。 (1) はmp186℃ (分解) の白色鱗片状結晶で, 非極性溶媒には不溶, 水, エタノール, ジメチルホルムアミド, ジメチルスルホキシドなどに可溶である。 (2) はmp238℃ (分解) の白色結晶で, その溶解性は (1) とほぼ同様であるが, エタノールには難溶である。(1) および (2) を酢酸ナトリウム存在下に無水酢酸でアセチル化すると閉環し, それぞれトリアゾール環を有する3-アセトアミド-5-メチル-1, 2, 4-トリアゾール, ならびに3, 5-ジアセトアミド-1, 2, 4-トリアゾールを生成する。なお, (2) を塩基性水溶液中で煮沸すると脱アンモニア閉環して3-アミノ-5-グアニルヒドラジノ-1, 2, 4-トリアゾール (3) を73.3%の好収率で得た。以上の結果からアミノグアニジン塩と臭化シアンとの反応では予想した3, 5-ジアミノ-1, 2, 4-トリアゾール (別名グアナゾール) は得られず, 直鎖状化合物を生成することがわかった。

著者

村橋 俊一

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.61, no.5, pp.425-435, 2003-05-01 (Released:2009-11-13)

参考文献数

60

被引用文献数

2 3

---

The discovery of a new chemical reaction often leads to new chemical principle and application. We found that low valent ruthenium, rhodium, iridium, and rhenium hydride complexes can be used as transition metal-based redox Lewis acid and base, and ambiphilic catalysts. Various substrates bearing α-hetero atom (pronucleophiles) such as nitriles, carbonyl compounds, isocyanates undergo α-C-H activation upon treatment with the transition-metal-based catalysts, and subsequent reaction with nucleophiles such as alkenes, alkynes, carbonyl compounds, imines, and nitriles give the products via carbon-carbon bond formations. Nitriles undergo reactions with either nucleophiles or electrophiles under neutral conditions in the presence of transition-metalbased redox Lewis acid catalysts. The catalysts can be used also as ambiphilic catalysts. With these catalysts multi-step reactions are carried out in one pot under neutral conditions, and are highly useful for combinatorial chemistry and the reactions in microreactor. The novel transition metal complex catalyzed reactions thus obtained would give various non-salt alternative processes for industry. The concept would provide an important way for green chemistry.

著者

吉川 誠次 山下 市二

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.35, no.5, pp.382-387, 1977-05-01 (Released:2009-11-13)

参考文献数

15

---

スパイスは矯臭, 調味, 薬効などによって, 食欲を増進し調理には欠くことができない重要性を持っている。硫黄化合物がスパイスの特異な作用の中心になっていることがわかったのは, それ程古いことではない。しかしその反応性が著しいことが機作の研究進歩を防げている。

著者

多羅間 公雄

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.27, no.1, pp.1-10, 1969-01-01 (Released:2009-11-13)

参考文献数

39

著者

宮下 正昭

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.54, no.10, pp.846-858, 1996 (Released:2009-11-16)

参考文献数

28

被引用文献数

4 4

---

Synthetic studies on nephilatoxins which has been carried out in the author's group is reviewed. Nephilatoxins (NPTX-112) isolated from Joro Spider (Nephila clavata) have been demonstrated to be potent blockers of glutaminergic neurotransmission as well as other spider toxins and are emerging as unique tools for understanding excitatory amino acid neurotransmission. In this report chemical synthesis of spider toxins involving synthetic strategy and total synthesis of NPTX-712 is described in which three azide intermediates were designed and employed as key compounds for construction of the characteristic polyamine chains of the toxins. In addition new results of biological activities obtained by using synthetic nephilatoxins (NPTX-712) and their congeners incorporating a D-amino acid are also described.

著者

山本 忠 吉武 誠 岸川 圭希 幸本 重男

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.50, no.7, pp.638-651, 1992-07-01 (Released:2010-01-28)

参考文献数

116

被引用文献数

3 4

---

Recent studies on intramolecular epoxide cyclizations were reviewed. Regio- and stereoselective anionic cyclization of epoxy-nitriles, -olefins, -carbamates and -alcohols were discussed. Also regio- and stereoselective Lewis acid promoted epoxide cyclizations, radical and paradium-catalyzed ones were described.

著者

上村 明男

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.62, no.7, pp.705-715, 2004-07-01 (Released:2009-11-13)

参考文献数

44

被引用文献数

4 7

---

Recent development of synthetic reactions using the Michael addition of thiols or analogues is described. Nucloephilic attack of thiolate anions to α, β-unsaturated ketones or esters generates enolate anions which are active to perform aldol reaction when the reaction condition is kept away from protic media. High stereoselectivity as well as enantioselectivity is achieved for the Michael/aldol tandem reaction when appropriate reaction conditions are employed. High regioselective Michael addition of thiols to unsymmetric fumaric derivatives is also accomplished and the either of regioisomers is prepared in a highly selective manner. The thio-groups introduced by these reactions serve as a useful precursor of carbon radicals that efficiently undergo cyclization reaction to provide heterocyclic compounds diastereoselectively.

著者

荒牧 稔

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.46, no.8, pp.821-823, 1988-08-01 (Released:2009-11-13)

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トリフルオロメタンスルホン酸はトリフリックアシッド (Triflic Acid) と呼ばれることもあるが, 前者の名称の方が公式名称である。

著者

赤井 周司 北 泰行

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.65, no.8, pp.772-782, 2007-08-01 (Released:2010-10-20)

参考文献数

52

被引用文献数

12 13

---

The lipase-catalyzed transesterification of alcohols with acyl donors in organic media has gained increased attention as a powerful method for the preparation of optically enriched compounds under very mild conditions, in which the vinyl esters 2 have been most frequently employed as the acyl donors; however, they are not always satisfactory.We applied the ethoxyvinyl esters 6 to the lipase-catalyzed transesterification reactions for the first time and discovered their advantages, viz., (i) the efficient reactivity and enantiotopic selectivity similar to or higher than those of 2 and (ii) the ready availability of the esters 6 having a suitably functionalized acyl moiety from the corresponding carboxylic acids and their applicability to the enzymatic reactions. These findings have opened a new possibility of the lipase-catalyzed reactions. In this review, several examples are introduced along with some related recent progress on the lipase-catalyzed asymmetric syntheses. The topics include (i) the enantioselective desymmetrization of prochiral 2, 2-disubstituted 1, 3-propanediols using 1-ethoxyvinyl 2-furoate 6b, (ii) the lipase-catalyzed domino reactions using suitably functionalized acyl donors 6e-i for the direct preparation of optically enriched cyclic compounds having multi stereogenic carbon centers, (iii) the dynamic kinetic resolution (DKR) of racemic secondary alcohols by the combined use of lipases and the ruthenium complexes 36a-g, and (iv) the DKR of racemic allylic alcohols (44, 45) by the combination of lipases and the vanadium compound 43. Application of these reactions to the asymmetric total synthesis of natural products is also described.

著者

安藤 能久

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.20, no.11, pp.1033-1040, 1962-11-01 (Released:2010-06-28)

参考文献数

28

著者

小方 芳郎

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.19, no.6, pp.438-448, 1961-06-01 (Released:2010-10-20)

参考文献数

108

被引用文献数

2

著者

周東 智 福岡 正哲 松田 彰

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.58, no.12, pp.1144-1154, 2000-12-01 (Released:2010-01-22)

参考文献数

20

被引用文献数

1 3

---

Cyclic ADP-ribose (cADPR, 1) is a newly discovered general mediator involved in Ca2+ signaling. The synthesis of cADPR analogs has been extensively studied by enzymatic and chemo-enzymatic methods using ADP-ribosylcyclase, due to their biological importance. ADP-ribosylcyclase from Aplysia Californica mediates the intramolecular ribosylation of NAD+ and some modified NAD+, which are prepared chemically or enzymatically, at the N-1-position of the purine moiety to yield cADPR or the corresponding analogs. However, the analogs that can be obtained by this method are limited due to the substrate-specificity of the enzyme. We developed an efficient method for the chemical synthesis of cADPR analogs and synthesized cyclic ADP-carbocyclicribose (cADPcR, 2) and its inosine congener (3, cIDPcR) as stable mimics of cADPR, in which an oxygen atom in the ribose ring of cADPR is replaced by a methylene group. Biological activities of cADPR and its analogs were also described.