(5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 2-propenoate | 1021498-34-9

• 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: (5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 2-propenoate
• CAS: 1021498-34-9
• 化学式: C₃₆H₆₀O₃Si
• 分子量: 568.956
• InChiKey: GAKDZAMUFZJBCV-GLPGDROISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.36
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 2-propenoate 在 Hoveyda-Grubbs catalyst second generation lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.5h， 生成 (5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-19-hydroxymethyl-9,10-secocholesta-5,7-dien-1-α-ol
  参考文献：
  名称：

  Synthesis of γ- and δ-lactones from 1α-hydroxy-5,6-trans-vitamin D3 by ring-closing metathesis route and their reduction with metal hydrides

  摘要：

  New synthetic pathway towards 19-functionalized derivatives of 1 alpha-hydroxy-5,6-transvitamin D-3 was described. Ring-closing metathesis (RCM) of 1 alpha-hydroxy-5,6-trans-vitamin D-3 1-omega-alkenoates was a key-step. Hydride reduction of resulting lactones led to the new vitamin D-3 analogues. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.03.005
• 作为产物：
  描述：

  丙烯酰氯 、 (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-2-methylene-cyclohexanol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以46%的产率得到(5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 2-propenoate
  参考文献：
  名称：

  Synthesis of γ- and δ-lactones from 1α-hydroxy-5,6-trans-vitamin D3 by ring-closing metathesis route and their reduction with metal hydrides

  摘要：

  New synthetic pathway towards 19-functionalized derivatives of 1 alpha-hydroxy-5,6-transvitamin D-3 was described. Ring-closing metathesis (RCM) of 1 alpha-hydroxy-5,6-trans-vitamin D-3 1-omega-alkenoates was a key-step. Hydride reduction of resulting lactones led to the new vitamin D-3 analogues. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.03.005