ethyl (4R,5R,8S,E)-9-(benzyloxy)-5-hydroxy-4,8-dimethylnon-2-enoate | 1123785-35-2

• 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: ethyl (4R,5R,8S,E)-9-(benzyloxy)-5-hydroxy-4,8-dimethylnon-2-enoate
• CAS: 1123785-35-2
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: ROMLZPPCFZCLCI-BBKYKLCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  24.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl (4R,5R,8S,E)-9-(benzyloxy)-5-hydroxy-4,8-dimethylnon-2-enoate 、 (S)-(-)-α-甲氧基-α-(三氟甲基)苯乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以76%的产率得到(4R,5R,8S,E)-ethyl-9-(benzyloxy)-4,8-dimethyl-5-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyloxy)non-2-enoate
  参考文献：
  名称：

  Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid

  摘要：

  A flexible and efficient asymmetric route to the synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W has been accomplished from commercially available 4-pentenoic acid. The successful generation of stereocenters was achieved by utilizing an Evans' chiral auxiliary-based alkylation and aldol reaction. Other key reactions such as a Julia-Kocienski olefination, Kita's macrolactonization, ring closing metathesis (RCM) reaction, and Yamaguchi's esterification were significant for the construction of the macrolactone cores. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.006
• 作为产物：
  描述：

  (S)-5-(benzyloxy)-4-methylpentan-1-ol 在 吡啶 、 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 重铬酸吡啶 、 三氟甲磺酸二丁硼 、 戴斯-马丁氧化剂 、 氟化氢吡啶 、 乙氧甲酰基亚甲基三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 33.17h， 生成 ethyl (4R,5R,8S,E)-9-(benzyloxy)-5-hydroxy-4,8-dimethylnon-2-enoate
  参考文献：
  名称：

  Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid

  摘要：

  A flexible and efficient asymmetric route to the synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W has been accomplished from commercially available 4-pentenoic acid. The successful generation of stereocenters was achieved by utilizing an Evans' chiral auxiliary-based alkylation and aldol reaction. Other key reactions such as a Julia-Kocienski olefination, Kita's macrolactonization, ring closing metathesis (RCM) reaction, and Yamaguchi's esterification were significant for the construction of the macrolactone cores. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.006