(Z)-2-癸烯酸叔丁酯 | 87947-77-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (Z)-2-癸烯酸叔丁酯
• 英文名称: (Z)-tert-Butyl 2-Decenoate
• 英文别名: tert-butyl (Z)-dec-2-enoate
• CAS: 87947-77-1
• 化学式: C₁₄H₂₆O₂
• 分子量: 226.359
• InChiKey: JBQPOENDUWMBPH-QXMHVHEDSA-N

物化性质

• 沸点：
  281.9±9.0 °C(Predicted)
• 密度：
  0.881±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• 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：

  (Z)-2-癸烯酸叔丁酯 在 palladium dihydroxide 正丁基锂 、 甲酸 、 morpholinium formate 作用下， 以 乙醇 为溶剂， 反应 0.58h， 生成 (3R)-tert-butyl 3-aminodecanoate
  参考文献：
  名称：

  An asymmetric ammonia synthon for Michael additions

  摘要：

  The highly diastereoselective 1,4-addition of lithiated chiral amine 1 to alpha,beta-unsaturated esters, followed by hydrogenolysis of the benzylic-type C-N bonds of the 1,4-adducts, provides an asymmetric ammonia synthon for Michael additions. Under optimized conditions, lithiated 1 adds to alpha,beta-unsaturated tert-butyl esters in dimethoxyethane at -63-degrees-C in high yield with very high diastereoselectivity. Small, large, functionalized, and chiral beta-ester substituents are amenable, with (S)-1 consistently adding to (E)-3 from the top as drawn in Table II. Hydrogenolysis liberates the beta-amino esters with typically 95-99% ee.

  DOI：

  10.1021/jo00033a037
• 作为产物：
  描述：

  erythro-tert-butyl 3-hydroxy-2-(trimethylgermyl)decanoate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-2-癸烯酸叔丁酯 、 trans-2-decenoic acid tert-butyl ester
  参考文献：
  名称：

  Peterson olefination reaction using (trimethylgermyl)acetate. Stereoselective synthesis of (E)-2-alkenoic acid esters

  摘要：

  Peterson-type reaction of (trimethylgermyl)acetates 1 with aldehydes and ketones 2 gave stereoselectively (E)-2-alkenoic acid esters (E)-4 after stirring at -78-degrees-C and warming to room temperature. High yields of the reaction intermediates threo- and erythro-3-hydroxy-2-(trimethylgermyl)alkanoic acid esters 3 were obtained when the reaction was quenched at -78-degrees-C. The paths for conversion of threo-3 and erythro-3 to (E)-4 are discussed.

  DOI：

  10.1021/jo00001a064

文献信息

• α-Substitution of 2-Alkenoic Esters via α-Carbanion Intermediates
  作者：Yoshiro Sato、Sachiyo Takeuchi

  DOI：10.1055/s-1983-30492

  日期：——
• Convenient Preparations of (Diphenylphosphono)acetic Acid Esters and the Comparison of the <i>Z</i>-Selectivities of Their Horner−Wadsworth−Emmons Reaction with Aldehydes Depending on the Ester Moiety
  作者：Kaori Ando

  DOI：10.1021/jo9907181

  日期：1999.10.1
• INOUE, SUMIE;SATO, YOSHIRO, J. ORG. CHEM., 56,(1991) N, C. 347-352
  作者：INOUE, SUMIE、SATO, YOSHIRO

  DOI：——

  日期：——