(4R,7R,E)-((2R,3S)-3-hydroxypent-4-en-2-yl) 7-(acryloyloxy)-4-hydroxyoct-2-enoate | 1369492-93-2

• 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: (4R,7R,E)-((2R,3S)-3-hydroxypent-4-en-2-yl) 7-(acryloyloxy)-4-hydroxyoct-2-enoate
• 英文别名: [(2R,3S)-3-hydroxypent-4-en-2-yl] (E,4R,7R)-4-hydroxy-7-prop-2-enoyloxyoct-2-enoate
• CAS: 1369492-93-2
• 化学式: C₁₆H₂₄O₆
• 分子量: 312.363
• InChiKey: XESZSTBNZZJRTB-DCOHZSIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,7R,E)-((2R,3S)-3-hydroxypent-4-en-2-yl) 7-(acryloyloxy)-4-hydroxyoct-2-enoate 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以80%的产率得到(3E,9E)-(5S,6R,11R,14R)-5,11-Dihydroxy-6,14-dimethyl-1,7-dioxa-cyclotetradeca-3,9-diene-2,8-dione
  参考文献：
  名称：

  Stereoselective total synthesis of clonostachydiol

  摘要：

  A simple and efficient stereoselective synthesis of clonostachydiol was achieved using ethyl (R)-3-hydroxybutanoate 5 and methyl (R)-2-hydroxypropanoate 12 as readily available starting materials. The key steps involved in the synthesis were MacMillan alpha-hydroxylation, Horner-Wadsworth-Emmons (HWE) olefination, a Grignard reaction, and Hoveyda-Grubbs IInd generation catalyzed ring closing metathesis (RCM). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.014
• 作为产物：
  描述：

  (-)-(5R)-5-(tert-butyldimethylsilyloxy)-hexanal 在 4-二甲氨基吡啶 、 copper(ll) sulfate pentahydrate 、 lithium hydroxide monohydrate 、 四氯化钛 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 L-脯氨酸 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 31.0h， 生成 (4R,7R,E)-((2R,3S)-3-hydroxypent-4-en-2-yl) 7-(acryloyloxy)-4-hydroxyoct-2-enoate
  参考文献：
  名称：

  Stereoselective total synthesis of clonostachydiol

  摘要：

  A simple and efficient stereoselective synthesis of clonostachydiol was achieved using ethyl (R)-3-hydroxybutanoate 5 and methyl (R)-2-hydroxypropanoate 12 as readily available starting materials. The key steps involved in the synthesis were MacMillan alpha-hydroxylation, Horner-Wadsworth-Emmons (HWE) olefination, a Grignard reaction, and Hoveyda-Grubbs IInd generation catalyzed ring closing metathesis (RCM). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.014

文献信息

• Stereoselective total synthesis of clonostachydiol
  作者：Udugu Ramulu、Dasari Ramesh、Singanaboina Rajaram、Sudina Purushotham Reddy、Kunuru Venkatesham、Yenamandra Venkateswarlu

  DOI：10.1016/j.tetasy.2012.01.014

  日期：2012.1

  A simple and efficient stereoselective synthesis of clonostachydiol was achieved using ethyl (R)-3-hydroxybutanoate 5 and methyl (R)-2-hydroxypropanoate 12 as readily available starting materials. The key steps involved in the synthesis were MacMillan alpha-hydroxylation, Horner-Wadsworth-Emmons (HWE) olefination, a Grignard reaction, and Hoveyda-Grubbs IInd generation catalyzed ring closing metathesis (RCM). (C) 2012 Elsevier Ltd. All rights reserved.