9α-(benzoyloxy)-(7E)-vitamin D3 tert-butyldimethylsilyl ether | 133447-42-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 9α-(benzoyloxy)-(7E)-vitamin D3 tert-butyldimethylsilyl ether
• CAS: 133447-42-4
• 化学式: C₄₀H₆₂O₃Si
• 分子量: 619.016
• InChiKey: JYYRUKAAQTYEIC-SFBNZNICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.48
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  9α-(benzoyloxy)-(7E)-vitamin D3 tert-butyldimethylsilyl ether 在 lithium aluminium tetrahydride 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 8.0h， 生成 9α-hydroxy-cis-isotachysterol3
  参考文献：
  名称：

  Stereoselective synthesis and thermal rearrangement of the first analog of 7(Z)-vitamin D

  摘要：

  The first (7Z)-vitamin D analogue, 15, was synthesized stereoselectively using, as the key step, Wittig-Horner coupling between an allylphosphine oxide anion and a alpha-benzoyloxy ketone. Compound 15 has the same triene system as the putative 7Z intermediate of the mechanism postulated by Okamura and co-workers for thermally induced [1,5]-sigmatropic hydrogen shifts in vinylallenes. Okamura's hypothesis is supported by the identity of the products of thermally induced [1,7]-sigmatropic hydrogen shifts in 15.

  DOI：

  10.1021/jo00011a024
• 作为产物：
  描述：

  维生素 D3 在 N-[(2,4-二氯苯氧基)-甲氧基硫代膦酰]丙-2-胺 吡啶 、 sodium tetrahydroborate 、 重铬酸吡啶 、 MoO5*pyridine*HMPA 、 甲基锂 、 4-甲基苯磺酸吡啶 、 臭氧 、 lithium bromide 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 29.33h， 生成 9α-(benzoyloxy)-(7E)-vitamin D3 tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Stereoselective synthesis and thermal rearrangement of the first analog of 7(Z)-vitamin D

  摘要：

  The first (7Z)-vitamin D analogue, 15, was synthesized stereoselectively using, as the key step, Wittig-Horner coupling between an allylphosphine oxide anion and a alpha-benzoyloxy ketone. Compound 15 has the same triene system as the putative 7Z intermediate of the mechanism postulated by Okamura and co-workers for thermally induced [1,5]-sigmatropic hydrogen shifts in vinylallenes. Okamura's hypothesis is supported by the identity of the products of thermally induced [1,7]-sigmatropic hydrogen shifts in 15.

  DOI：

  10.1021/jo00011a024