(S)-(+)-5-(dec-1-ynyl)-tetrahydrofuran-2-one | 72151-70-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-(+)-5-(dec-1-ynyl)-tetrahydrofuran-2-one
• 英文别名: (S)-5-(1-decynyl)oxacyclopentan-2-one；(S)-(-)-5-tetradecyn-4-olide；(5S)-5-dec-1-ynyloxolan-2-one
• CAS: 72151-70-3
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: BIGQAZKDYXXFSF-CYBMUJFWSA-N

物化性质

• 沸点：
  357.4±31.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-5-(dec-1-ynyl)-tetrahydrofuran-2-one 在 palladium on activated charcoal 喹啉 、 氢气 作用下， 以 正戊烷 为溶剂， 反应 5.0h， 以89%的产率得到(S)-japonilure
  参考文献：
  名称：

  Convergent and enantioselective syntheses of both enantiomers of (5Z)-tetradecen-4-olide, scarab beetle pheromones

  摘要：

  Japonilure and its enantiomer, that is, (R)-(-)- and (S)-(+)-(5Z)-tetradecen-4-olide, have been synthesised in satisfactory overall yields using a highly convergent procedure. In situ prepared 1-decynylethylzine was enantioselectively coupled to isopropyl 4-oxobutanoate in the presence of (S)- or (R)-BINOL. The alkoxy-ester intermediates obtained were cyclised to the corresponding substituted gamma-lactones, carrying a triple bond in the side chain. Lindlar-hydrogenation of the latter yielded the target compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.006
• 作为产物：
  描述：

  methyl (R)-4-hydroxy-5-tetradecynoate 在 sodium hydroxide 、 对甲苯磺酸 作用下， 以 乙醚 为溶剂， 反应 115.0h， 生成 (S)-(+)-5-(dec-1-ynyl)-tetrahydrofuran-2-one
  参考文献：
  名称：

  Preparation of Enantiomerically Enriched Compounds Using Enzymes; VII.¹A Synthesis of Japanese Beetle Pheromone Utilizing Lipase-Catalyzed Enantioselective Lactonization

  摘要：

  日本牛色素(R,Z)-(-)-5-(1- decenyl)-2-oxo-tetrahydrofuran,是通过种类密钥中介甲基(RS)-4-hydroxy-5-tetradecynoate的酶选择性乳化合成。

  DOI：

  10.1055/s-1990-27105

文献信息

• Asymmetric synthesis via axially dissymmetric molecules. 7. Synthetic applications of the enantioselective reduction by binaphthol-modified lithium aluminum hydride reagents
  作者：R. Noyori、I. Tomino、M. Yamada、M. Nishizawa

  DOI：10.1021/ja00334a042

  日期：1984.10

  La reaction est applicable a une variete de composes carbonyles insatures de structures diverses tels que, cetones aromatiques, cetones acetyleniques, cetones ethyleniques et aldehydes. L'utilite est illustree par la synthese fortement stereocontrolee d'intermediaires de prostaglandines, de quelques pheromones d'insectes, d'alcools terpeniques primaires chiraux, de phenyloxiranne optiquement actif

  La 反应 est 适用一个 une variete de composes carbonyles insatures destructures different tels que, cetones aromatiques, cetones acetyleniques, cetones ethyleniques et aldehydes。L'utilite est illustree par la synthese fortement Stereocontrolee d'intermediaires de prostaglandines, de quelques pheromones d'insectes, d'alcools terpeniques primaires chiraux, de phenyloxiranne optiquement actif...
• Lipase-catalyzed kinetic resolution of methyl 4-hydroxy-5-tetradecynoate and its application to a facile synthesis of japanese beetle pheromone
  作者：Eiichiro Fukusaki、Shuji Senda、Yutaka Nakazono、Tetsuo Omata

  DOI：10.1016/s0040-4020(01)86554-6

  日期：1991.8

  solvent yields methyl (R)-4-succinoyloxy-5-tetradecynoate with over 90% e.e.. Furthermore, this optically active diester was converted to (R)-5-(1-decynyl)oxacyclopentan-2-one by lipase-catalyzed enantioselective lactonization which enhanced its e.e. over 99%. The Japanese beetle pheromone (R,Z)-(-)-5-(1-decenyl)oxacyclopentan-2-one is synthesized in one step from this optically active lactone.

  通过在有机溶剂中脂肪酶催化的对映选择性酰化作用，可以实现4-羟基-5-十四碳烯酸甲酯的动力学拆分。在有机溶剂中将4-羟基-5-十四碳烯酸甲酯与琥珀酸酐酰化，可得到具有超过90％ee的（R）-4-琥珀酰氧基-5-十四碳烯酸甲酯。此外，该光学活性二酯通过脂肪酶催化的对映选择性内酯化作用转化为（R）-5-（1-癸炔基）氧杂环戊烷-2-酮，其ee提高了99％以上。由该光学活性内酯一步合成日本甲虫信息素（R，Z）-（-）-5-（1-癸烯基）氧环戊烷-2-酮。
• SUGAI, TAKESHI;OHSAWA, SHOKO;YAMADA, HIROSHI;OHTA, HIROMICHI, SYNTHESIS,(1990) N2, C. 1112-1114
  作者：SUGAI, TAKESHI、OHSAWA, SHOKO、YAMADA, HIROSHI、OHTA, HIROMICHI

  DOI：——

  日期：——
• Preparation of Enantiomerically Enriched Compounds Using Enzymes; VII.¹A Synthesis of Japanese Beetle Pheromone Utilizing Lipase-Catalyzed Enantioselective Lactonization
  作者：Takeshi Sugai、Shoko Ohsawa、Hiroshi Yamada、Hiromichi Ohta

  DOI：10.1055/s-1990-27105

  日期：——

  The Japanese beetle pheromone, (R,Z)-(-)-5-(1-decenyl)-2-oxo-tetrahydrofuran, was synthesized by means of the enzymatic enantioselective lactonization of the racemic key-intermediate methyl (RS)-4-hydroxy-5-tetradecynoate.

  日本牛色素(R,Z)-(-)-5-(1- decenyl)-2-oxo-tetrahydrofuran,是通过种类密钥中介甲基(RS)-4-hydroxy-5-tetradecynoate的酶选择性乳化合成。
• Convergent and enantioselective syntheses of both enantiomers of (5Z)-tetradecen-4-olide, scarab beetle pheromones
  作者：Alcindo A. Dos Santos、Wittko Francke

  DOI：10.1016/j.tetasy.2006.09.006

  日期：2006.10

  Japonilure and its enantiomer, that is, (R)-(-)- and (S)-(+)-(5Z)-tetradecen-4-olide, have been synthesised in satisfactory overall yields using a highly convergent procedure. In situ prepared 1-decynylethylzine was enantioselectively coupled to isopropyl 4-oxobutanoate in the presence of (S)- or (R)-BINOL. The alkoxy-ester intermediates obtained were cyclised to the corresponding substituted gamma-lactones, carrying a triple bond in the side chain. Lindlar-hydrogenation of the latter yielded the target compounds. (c) 2006 Elsevier Ltd. All rights reserved.