ethyl (E)-3-[(2S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]prop-2-enoate | 136881-02-2

• 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: ethyl (E)-3-[(2S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]prop-2-enoate
• CAS: 136881-02-2
• 化学式: C₁₄H₂₆O₄Si
• 分子量: 286.444
• InChiKey: XKSMGPQVOWSBNG-VDTGWRSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  48.06
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-[(2S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]prop-2-enoate 在 二异丁基氢化铝 作用下， 生成
  参考文献：
  名称：

  Rearrangement of epoxides in non-aldol aldol process: Allylic vs. Tertiary and secondary carbocationic centers

  摘要：

  It has been shown that allylic carbocations are formed in preference to tertiary or secondary carbocations in the rearrangement of substituted epoxides. However protection of the alkene as a bromo ether allows for the desired rearrangement and production of intermediates for the synthesis of the cytotoxic tedanolides. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00458-x
• 作为产物：
  描述：

  (E)-4-(叔丁基二甲基甲硅烷基氧基)-2-丁烯-1-醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二异丙酯 作用下， 生成 ethyl (E)-3-[(2S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]prop-2-enoate
  参考文献：
  名称：

  Rearrangement of epoxides in non-aldol aldol process: Allylic vs. Tertiary and secondary carbocationic centers

  摘要：

  It has been shown that allylic carbocations are formed in preference to tertiary or secondary carbocations in the rearrangement of substituted epoxides. However protection of the alkene as a bromo ether allows for the desired rearrangement and production of intermediates for the synthesis of the cytotoxic tedanolides. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00458-x

文献信息

• Stereospecific methylation of .gamma.,.delta.-epoxy acrylates by trimethylaluminum: a method for the iterative construction of polypropionate chains
  作者：Masaaki Miyashita、Masahide Hoshino、Akira Yoshikoshi

  DOI：10.1021/jo00023a001

  日期：1991.11

  A new and potentially useful method for the synthesis of polypropionates via the regio- and stereo-specific methylation of gamma,delta-epoxy acrylates by (CH3)3Al has been developed.