(4Z,8E)-10-(tert-butyldiphenylsilyloxy)-4,8-decadien-1-ol | 307497-77-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4Z,8E)-10-(tert-butyldiphenylsilyloxy)-4,8-decadien-1-ol
• CAS: 307497-77-4
• 化学式: C₂₆H₃₆O₂Si
• 分子量: 408.656
• InChiKey: NWMXTGMCNJRJQX-NKKZRYADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  29.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4Z,8E)-10-(tert-butyldiphenylsilyloxy)-4,8-decadien-1-ol 在 吡啶 、 disodium hydrogenphosphate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Chloro-methanesulfonic acid 3-(3-{2-[(2S,3S)-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-ethyl}-oxiranyl)-propyl ester
  参考文献：
  名称：

  Transformation of cis-Epoxy Compound to cis-2,3-Disubstituted Oxane and Investigation on Propagation Step in the Ring-Expansion Reactions of cis,trans-Diepoxy Systems

  摘要：

  Conversion of cis-epoxy compounds by successive ring-expansion reaction into trans-fused cyclic ethers was examined from both the initiation step and the propagation step. The ring-expansion reaction of cis-4,5-epoxy compounds containing a leaving group on C-1 was attempted as a unit process for the successive reaction. When a chloromesyl group was used as a leaving group, the ring expansion proceeded to give an oxane derivative (endo-type product) preferentially. On the other hand, investigation of the propagation step was carried out with respect to epoxy oxane derivatives. It was clarified that the ring-expansion reaction of cis-2,3-disubstituted oxane derivatives provided spiro acetals as products, not the desired trans-fused cyclic ethers, owing to the reaction pathway triggered by 1,2-hydride rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00622-0
• 作为产物：
  描述：

  (2E,6Z)-1-(tert-butyldiphenylsilyloxy)-10-(4'-methoxybenzyloxy)-2,6-decadiene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以81%的产率得到(4Z,8E)-10-(tert-butyldiphenylsilyloxy)-4,8-decadien-1-ol
  参考文献：
  名称：

  Transformation of cis-Epoxy Compound to cis-2,3-Disubstituted Oxane and Investigation on Propagation Step in the Ring-Expansion Reactions of cis,trans-Diepoxy Systems

  摘要：

  Conversion of cis-epoxy compounds by successive ring-expansion reaction into trans-fused cyclic ethers was examined from both the initiation step and the propagation step. The ring-expansion reaction of cis-4,5-epoxy compounds containing a leaving group on C-1 was attempted as a unit process for the successive reaction. When a chloromesyl group was used as a leaving group, the ring expansion proceeded to give an oxane derivative (endo-type product) preferentially. On the other hand, investigation of the propagation step was carried out with respect to epoxy oxane derivatives. It was clarified that the ring-expansion reaction of cis-2,3-disubstituted oxane derivatives provided spiro acetals as products, not the desired trans-fused cyclic ethers, owing to the reaction pathway triggered by 1,2-hydride rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00622-0