9α-hydroxy-(7E)-vitamin D3 | 133447-44-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 9α-hydroxy-(7E)-vitamin D3
• 英文别名: (7E)-9-Hydroxyvitamin D3；(1R,3aR,4E,5R,7aR)-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-5-ol
• CAS: 133447-44-6
• 化学式: C₂₇H₄₄O₂
• 分子量: 400.645
• InChiKey: JEGAVWSSLLSTNZ-FOYCDMTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9α-hydroxy-(7E)-vitamin D3 以 甲苯 为溶剂， 生成 (3S,9S,10S)-(Z,Z)-9,10-secocholesta-5,7,14-triene-3,9-diol
  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 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 MoO5*pyridine*HMPA 、 四丁基氟化铵 、 甲基锂 、 4-甲基苯磺酸吡啶 、 臭氧 、 lithium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 34.33h， 生成 9α-hydroxy-(7E)-vitamin D3
  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

• Fluorinated chirons for vitamin D3 syntheses. A serendipitous synthesis of a 9.alpha.-hydroxy derivative of (7Z)-vitamin D3
  作者：William G. Dauben、Laura J. Greenfield

  DOI：10.1021/jo00031a050

  日期：1992.2
• 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：——