(E,8R)-8-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-methylnon-3-en-2-ol | 185099-82-5

• 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: (E,8R)-8-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-methylnon-3-en-2-ol
• CAS: 185099-82-5
• 化学式: C₄₁H₇₄O₃Si₂
• 分子量: 671.208
• InChiKey: AENBKSWWEDLSCQ-QMUDCDDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.32
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E,8R)-8-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-methylnon-3-en-2-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以94%的产率得到solverol
  参考文献：
  名称：

  Synthesis and in vitro evaluation of side chain-unsaturated analogs of 24a,24b-dihomo-1,25-dihydroxycholecalciferol

  摘要：

  A synthesis and an in vitro evaluation of side chain-unsaturated analogs 3 and 4 of 24a,24b-dihomo-1,25-dihydroxycholecalciferol (1) are described. Novel C-23a,C-24-vitamin D synthons (sulfone 10 and aldehyde 11) were used for the synthesis of analog 4 and for the efficient preparation of the parent compound 1. The synthetic approach developed allows the use of easily available side chain fragments, such as oxirane 12 or Wittig reagent 15 for the preparation of compound 1 and analog 4, respectively. Introduction of 24aE double bond bond results in a selective, 1000-fold increase in the binding affinity of analog 4 for the vitamin D receptor, compared to the affinity of 1, whereas the affinity of 4 for the vitamin D-binding protein and the activity in stimulating the differentiation of human promyelocytic leukemia HL-60 cells remained largely unchanged. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00040-8
• 作为产物：
  描述：

  methyl (5R)-5-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-5-acetyloxy-3-hydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]hexanoate 在 咪唑 、 氢氧化钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.5h， 生成 (E,8R)-8-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-methylnon-3-en-2-ol
  参考文献：
  名称：

  Synthesis and in vitro evaluation of side chain-unsaturated analogs of 24a,24b-dihomo-1,25-dihydroxycholecalciferol

  摘要：

  A synthesis and an in vitro evaluation of side chain-unsaturated analogs 3 and 4 of 24a,24b-dihomo-1,25-dihydroxycholecalciferol (1) are described. Novel C-23a,C-24-vitamin D synthons (sulfone 10 and aldehyde 11) were used for the synthesis of analog 4 and for the efficient preparation of the parent compound 1. The synthetic approach developed allows the use of easily available side chain fragments, such as oxirane 12 or Wittig reagent 15 for the preparation of compound 1 and analog 4, respectively. Introduction of 24aE double bond bond results in a selective, 1000-fold increase in the binding affinity of analog 4 for the vitamin D receptor, compared to the affinity of 1, whereas the affinity of 4 for the vitamin D-binding protein and the activity in stimulating the differentiation of human promyelocytic leukemia HL-60 cells remained largely unchanged. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00040-8