(S)-4-hydroxy-5-hexenoic acid methyl ester

• 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: (S)-4-hydroxy-5-hexenoic acid methyl ester
• 英文别名: methyl (S)-4-hydroxyhex-5-enoate；methyl (4S)-4-hydroxyhex-5-enoate
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: NQAAMXMAYNICPG-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (S)-4-hydroxy-5-hexenoic acid methyl ester 在 咪唑 、 2,4,6-三氯苯甲酰氯 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 (R)-1-((2S,3R)-3-vinyloxiran-2-yl)ethyl (S)-4-((tert-butyldimethylsilyl)oxy)hex-5-enoate
  参考文献：
  名称：

  首次立体选择性全合成和壬酸酯（-）-stagonolide D绝对结构的重新确认

  摘要：

  已经完成了壬烯内酯（-）-stagonolide D的第一个立体选择性全合成。Midland高山硼烷还原反应可在C4处安装羟基，Henbest环氧化法可在C7和C8之间立体选择性地引入环氧化物，山口酯化反应和烯烃复分解反应是整个合成过程中的关键步骤。

  DOI：

  10.1016/j.tetlet.2016.12.042
• 作为产物：
  描述：

  葡萄糖酸内酯 在 甲醇 、 copper(l) iodide 、 三甲基氯硅烷 、 氢溴酸 、 三正丁基氢锡 、 溶剂黄146 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (S)-4-hydroxy-5-hexenoic acid methyl ester
  参考文献：
  名称：

  Homochiral 4-hydroxy-5-hexenoic acids and their derivatives and homologues from carbohydrates

  摘要：

  Efficient routes to chiral 4-hydroxy-5-hexenoic acids and lactones from D-gluconic acid-delta -lactone and L-mannonic acid-gamma -lactone are described. In this approach, the starting lactones are converted to 2,6-dibromo compounds that readily undergo zinc mediated elimination to generate the terminal alkene group in concert with 2-deoxygenation. The integrity of the remaining stereocenters is preserved during the reaction. The related important pharmaceutical intermediates (S)-3-hydroxy-4-pentenoic acid and (S)-1.3-dihydroxy-4-pentene were also prepared from 2-deoxyribose via the corresponding aldonolactone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00053-2

文献信息

• First stereoselective total synthesis and reconfirmation of absolute structure of nonenolide (−)-stagonolide D
  作者：A. Sravanth Kumar、K. Praneeth、P. Srihari、J.S. Yadav

  DOI：10.1016/j.tetlet.2016.12.042

  日期：2017.2

  The first stereoselective total synthesis of nonenolide (−)-stagonolide D has been accomplished. Midland Alpine borane reduction to install hydroxyl group at C4, Henbest epoxidation to introduce epoxide stereoselectively between C7 and C8, Yamaguchi esterification and Olefin metathesis reaction are the key steps involved in the total synthesis.

  已经完成了壬烯内酯（-）-stagonolide D的第一个立体选择性全合成。Midland高山硼烷还原反应可在C4处安装羟基，Henbest环氧化法可在C7和C8之间立体选择性地引入环氧化物，山口酯化反应和烯烃复分解反应是整个合成过程中的关键步骤。
• Homochiral 4-hydroxy-5-hexenoic acids and their derivatives and homologues from carbohydrates
  作者：Jie Song、Rawle I. Hollingsworth

  DOI：10.1016/s0957-4166(01)00053-2

  日期：2001.3

  Efficient routes to chiral 4-hydroxy-5-hexenoic acids and lactones from D-gluconic acid-delta -lactone and L-mannonic acid-gamma -lactone are described. In this approach, the starting lactones are converted to 2,6-dibromo compounds that readily undergo zinc mediated elimination to generate the terminal alkene group in concert with 2-deoxygenation. The integrity of the remaining stereocenters is preserved during the reaction. The related important pharmaceutical intermediates (S)-3-hydroxy-4-pentenoic acid and (S)-1.3-dihydroxy-4-pentene were also prepared from 2-deoxyribose via the corresponding aldonolactone. (C) 2001 Elsevier Science Ltd. All rights reserved.