(4R) ethyl 4-hydroxy-(E)-hept-2-enoate | 107736-36-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4R) ethyl 4-hydroxy-(E)-hept-2-enoate
• 英文别名: ethyl (R,E)-4-hydroxyhept-2-enoate；(R)-(E)-ethyl 4-hydroxyhept-2-enoate；ethyl (E,4R)-4-hydroxyhept-2-enoate
• CAS: 107736-36-7
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: QBWJOBQGZHROSL-HYDMIIDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R) ethyl 4-hydroxy-(E)-hept-2-enoate 在 sodium tetrahydroborate 、 氢气 、 nickel diacetate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以60%的产率得到ethyl (R)-4-hydroxyheptanoate
  参考文献：
  名称：

  Thijs, Lambertus; Waanders, Peter P.; Stokkingreef, Edwin H. M., Recueil des Travaux Chimiques des Pays-Bas, 1986, vol. 105, p. 332 - 337

  摘要：

  DOI：
• 作为产物：
  描述：

  正戊醛 在 copper(ll) sulfate pentahydrate 、 L-脯氨酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 37.0h， 生成 (4R) ethyl 4-hydroxy-(E)-hept-2-enoate
  参考文献：
  名称：

  Formal synthesis of pinolide via l-proline-catalyzed sequential α-aminooxylation, Horner–Wadsworth–Emmons olefination and Sharpless asymmetric dihydroxylation

  摘要：

  A convergent, formal enantioselective synthesis of pinolide, a new nonenolide, has been achieved with high enantiomeric purity (99% ee) starting from readily available raw materials. The main highlight of the synthetic strategy is the application of L-proline catalyzed sequential alpha-aminooxylation and Horner-Wadsworth-Emmons olefination of an aldehyde, Sharpless asymmetric dihydroxylation and Steglich esterification as the key steps for the construction of a key chiral intermediate of the target molecule. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.01.005

文献信息

• Organocatalytic sequential α-aminoxylation and cis-Wittig olefination of aldehydes: synthesis of enantiopure γ-butenolides
  作者：Dattatray A. Devalankar、Pandurang V. Chouthaiwale、Arumugam Sudalai

  DOI：10.1016/j.tetasy.2012.02.004

  日期：2012.2

  A short route to enantiopure gamma-butenolides (up to 99% ee) has been developed from readily available starting materials. The strategy involves a sequential organocatalytic alpha-aminoxylation followed by cis-Wittig olefination of aldehydes. The utility of this protocol has been demonstrated in the asymmetric synthesis of trans-(+)-cognac lactone with high enantiomeric purity. (C) 2012 Elsevier Ltd. All rights reserved.