De-A,B-9α-(benzoyloxy)cholestan-8-one | 133447-41-3

• 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: De-A,B-9α-(benzoyloxy)cholestan-8-one
• 英文别名: [(1R,3aR,5R,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-4-oxo-2,3,3a,5,6,7-hexahydro-1H-inden-5-yl] benzoate
• CAS: 133447-41-3
• 化学式: C₂₅H₃₆O₃
• 分子量: 384.559
• InChiKey: FPSGDRCEWJQBFB-ZOINAQCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.07
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  De-A,B-9α-(benzoyloxy)cholestan-8-one 在 lithium aluminium tetrahydride 、 四丁基氟化铵 、 甲基锂 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 38.5h， 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 、 4-甲基苯磺酸吡啶 、 臭氧 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 25.83h， 生成 De-A,B-9α-(benzoyloxy)cholestan-8-one
  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

文献信息

• MAESTRO, MIGUEL A.;SARDINA, F. JAVIER;CASTEDO, LUIS;MOURINO, ANTONIO, J. ORG. CHEM., 56,(1991) N1, C. 3582-3587
  作者：MAESTRO, MIGUEL A.、SARDINA, F. JAVIER、CASTEDO, LUIS、MOURINO, ANTONIO

  DOI：——

  日期：——
• Stereoselective synthesis and thermal rearrangement of the first analog of 7(Z)-vitamin D
  作者：Miguel A. Maestro、F. Javier Sardina、Luis Castedo、Antonio Mourino

  DOI：10.1021/jo00011a024

  日期：1991.5

  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.