(E)-6-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-hex-3-enal | 229031-94-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-6-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-hex-3-enal
• 英文别名: (E)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methyl-6-phenylmethoxyhex-3-enal
• CAS: 229031-94-1
• 化学式: C₂₁H₃₄O₃Si
• 分子量: 362.585
• InChiKey: LKLDKUYIWYRJDN-WOJGMQOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-6-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-hex-3-enal 生成 (4S,5R)-5-((E)-4-Benzyloxy-1-methyl-but-1-enyl)-4-methyl-[1,3]dioxan-2-one
  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：

  [(2R,3S)-3-((E)-4-Benzyloxy-1-methyl-but-1-enyl)-oxiranylmethoxy]-tert-butyl-dimethyl-silane 在 三氟化硼乙醚 作用下， 生成 (E)-6-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-hex-3-enal 、 (E)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hept-4-en-2-one
  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