(S,E)-ethyl 6-hydroxy-3-methyl-6-((R)-oxiran-2-yl)-hex-2-enoate

• 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,E)-ethyl 6-hydroxy-3-methyl-6-((R)-oxiran-2-yl)-hex-2-enoate
• 英文别名: ethyl (E,6S)-6-hydroxy-3-methyl-6-[(2R)-oxiran-2-yl]hex-2-enoate
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: SODQEVMFTNKMGZ-JSJQHLISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,E)-ethyl 6-hydroxy-3-methyl-6-((R)-oxiran-2-yl)-hex-2-enoate 在 bis(cyclopentadienyl)titanium (III) chloride 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 17.0h， 以68%的产率得到(4aS,7S,7aS)-7-hydroxy-4a-methylhexahydrocyclopenta[c]pyran-3(1H)-one
  参考文献：
  名称：

  Formal synthesis of degraded sterol (+)-aplykurodinone-1

  摘要：

  The formal synthesis of aplykurodinone-1 is accomplished starting from a suitably functionalized bicyclic lactone having the requisite cis-fused ring junction with a quaternary chiral center that was assembled following a Cp2TiCl-mediated radical cyclization protocol. Our synthetic route further elaborates implementation of Grubbs ring closing metathesis (RCM), Eschenmoser-Claisen rearrangement and iodo-lactonization reactions for the synthesis of the final tricyclic precursor of the target molecule. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.026
• 作为产物：
  描述：

  5-羟基-2-戊酮 在 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 草酰氯 、 L-(+)-酒石酸二异丙酯 、 camphor-10-sulfonic acid 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 63.42h， 生成 (S,E)-ethyl 6-hydroxy-3-methyl-6-((R)-oxiran-2-yl)-hex-2-enoate
  参考文献：
  名称：

  Formal synthesis of degraded sterol (+)-aplykurodinone-1

  摘要：

  The formal synthesis of aplykurodinone-1 is accomplished starting from a suitably functionalized bicyclic lactone having the requisite cis-fused ring junction with a quaternary chiral center that was assembled following a Cp2TiCl-mediated radical cyclization protocol. Our synthetic route further elaborates implementation of Grubbs ring closing metathesis (RCM), Eschenmoser-Claisen rearrangement and iodo-lactonization reactions for the synthesis of the final tricyclic precursor of the target molecule. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.026

文献信息

• Formal synthesis of degraded sterol (+)-aplykurodinone-1
  作者：Nishant Singh、Kiran Kumar Pulukuri、Tushar Kanti Chakraborty

  DOI：10.1016/j.tet.2015.05.026

  日期：2015.7

  The formal synthesis of aplykurodinone-1 is accomplished starting from a suitably functionalized bicyclic lactone having the requisite cis-fused ring junction with a quaternary chiral center that was assembled following a Cp2TiCl-mediated radical cyclization protocol. Our synthetic route further elaborates implementation of Grubbs ring closing metathesis (RCM), Eschenmoser-Claisen rearrangement and iodo-lactonization reactions for the synthesis of the final tricyclic precursor of the target molecule. (C) 2015 Elsevier Ltd. All rights reserved.