(2S,3S)-3-Hydroxymethyl-2-vinyl-hex-5-ene-1,4-diol | 763105-50-6

• 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: (2S,3S)-3-Hydroxymethyl-2-vinyl-hex-5-ene-1,4-diol
• 英文别名: (2S,3S)-2-ethenyl-3-(hydroxymethyl)hex-5-ene-1,4-diol
• CAS: 763105-50-6
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: QVAHCLFBORRWPA-ZAZKALAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-Hydroxymethyl-2-vinyl-hex-5-ene-1,4-diol 在 咪唑 、 4-二甲氨基吡啶 、 Grubbs catalyst first generation 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 9.0h， 生成 (4R,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopent-2-enol
  参考文献：
  名称：

  Alkoxy group facilitated ring closing metathesis (RCM) of acyclic 1,6-dienes. Convenient synthesis of non-racemic highly substituted cyclopentenols

  摘要：

  Alkoxymethyl groups at the C-5 allylic position of 1,6-dienols have been found to accelerate RCM reactions significantly with the Grubbs' catalyst PhCH=Ru(PCY3)(2)Cl-2. This phenomenon has been used for direct access to highly substituted cyclopentenols, potential intermediates in the synthesis of carbovir, abacavir and BCA. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.127
• 作为产物：
  描述：

  (2R,3R)-3-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-2-(1-hydroxy-allyl)-pent-4-enoic acid ethyl ester 生成 (2S,3S)-3-Hydroxymethyl-2-vinyl-hex-5-ene-1,4-diol
  参考文献：
  名称：

  Alkoxy group facilitated ring closing metathesis (RCM) of acyclic 1,6-dienes. Convenient synthesis of non-racemic highly substituted cyclopentenols

  摘要：

  Alkoxymethyl groups at the C-5 allylic position of 1,6-dienols have been found to accelerate RCM reactions significantly with the Grubbs' catalyst PhCH=Ru(PCY3)(2)Cl-2. This phenomenon has been used for direct access to highly substituted cyclopentenols, potential intermediates in the synthesis of carbovir, abacavir and BCA. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.127

文献信息

• Alkoxy group facilitated ring closing metathesis (RCM) of acyclic 1,6-dienes. Convenient synthesis of non-racemic highly substituted cyclopentenols
  作者：Abhijit Nayek、Shyamapada Banerjee、Saikat Sinha、Subrata Ghosh

  DOI：10.1016/j.tetlet.2004.06.127

  日期：2004.8

  Alkoxymethyl groups at the C-5 allylic position of 1,6-dienols have been found to accelerate RCM reactions significantly with the Grubbs' catalyst PhCH=Ru(PCY3)(2)Cl-2. This phenomenon has been used for direct access to highly substituted cyclopentenols, potential intermediates in the synthesis of carbovir, abacavir and BCA. (C) 2004 Elsevier Ltd. All rights reserved.