3-hydroxyhept-6-ynethioic acid S-benzyl 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: 3-hydroxyhept-6-ynethioic acid S-benzyl ester
• 英文别名: S-benzyl 3-hydroxyhept-6-ynethioate
• 化学式: C₁₄H₁₆O₂S
• 分子量: 248.346
• InChiKey: BDFYBBDZSMHVNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-pentyn-1-al 、 S-benzyl hydrogen thiomalonate 在 copper(II) 2-ethylhexanoate 、 5-甲氧基苯并咪唑 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以65%的产率得到3-hydroxyhept-6-ynethioic acid S-benzyl ester
  参考文献：
  名称：

  An Exceptionally Mild Catalytic Thioester Aldol Reaction Inspired by Polyketide Biosynthesis

  摘要：

  This report details our discovery of a new catalytic ester aldol reaction using malonic acid half thioesters (MAHTs) that directly affords beta-hydroxythioesters. The reaction is catalyzed by combination of a Cu(II) salt and an amine base, and it can be performed under exceptionally mild conditions (23 degrees C, open to the air, wet solvent). Methyl malonic acid half thioesters afforded syn aldol products with distereoselectivities greater than 6:1.

  DOI：

  10.1021/ja029452x

文献信息

• An Exceptionally Mild Catalytic Thioester Aldol Reaction Inspired by Polyketide Biosynthesis
  作者：Gojko Lalic、Allen D. Aloise、Matthew D. Shair

  DOI：10.1021/ja029452x

  日期：2003.3.1

  This report details our discovery of a new catalytic ester aldol reaction using malonic acid half thioesters (MAHTs) that directly affords beta-hydroxythioesters. The reaction is catalyzed by combination of a Cu(II) salt and an amine base, and it can be performed under exceptionally mild conditions (23 degrees C, open to the air, wet solvent). Methyl malonic acid half thioesters afforded syn aldol products with distereoselectivities greater than 6:1.