(1R,4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one | 866430-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: (1R,4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one
• 英文别名: (4R,8aR,9R,12S,12aR)-12-[tert-butyl(diphenyl)silyl]oxy-9-hydroxy-4-methyl-1,4,5,6,7,8,8a,9,12,12a-decahydro-3-benzoxecin-2-one
• CAS: 866430-89-9
• 化学式: C₃₀H₄₀O₄Si
• 分子量: 492.731
• InChiKey: RLFAQEZUOVKACM-FJUXYKJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one 在 重铬酸吡啶 、 4 Angstroem MS 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (+)-11-epi-Sch 642305
  参考文献：
  名称：

  Enantioselective synthesis of epi-(+)-Sch 642305: observation of an interesting diastereoselection during RCM

  摘要：

  In an approach towards the enantioselective total synthesis of the novel bioactive natural product Sch 642305, an unusual diastereoselection during the key RCM reaction, resulted in the synthesis of the 11-epi-isorner of Sch 642305. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.07.152
• 作为产物：
  描述：

  (1R,2S,6S,7R,8S)-6-[tert-butyl(dimethyl)silyl]oxytricyclo[6.2.1.02,7]undeca-4,9-dien-3-one 在 Wilkinson's catalyst 、 Grubbs catalyst first generation 咪唑 、 titanium(IV) isopropylate 、 sodium tetrahydroborate 、 copper(l) iodide 、 cerium(III) chloride 、 氢气 、 4-甲基苯磺酸吡啶 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二苯醚 、 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， -78.0~220.0 ℃ 、101.33 kPa 条件下， 反应 81.17h， 生成 (1R,4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one
  参考文献：
  名称：

  Enantioselective synthesis of epi-(+)-Sch 642305: observation of an interesting diastereoselection during RCM

  摘要：

  In an approach towards the enantioselective total synthesis of the novel bioactive natural product Sch 642305, an unusual diastereoselection during the key RCM reaction, resulted in the synthesis of the 11-epi-isorner of Sch 642305. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.07.152

文献信息

• Enantioselective synthesis of epi-(+)-Sch 642305: observation of an interesting diastereoselection during RCM
  作者：Goverdhan Mehta、Harish M. Shinde

  DOI：10.1016/j.tetlet.2005.07.152

  日期：2005.9

  In an approach towards the enantioselective total synthesis of the novel bioactive natural product Sch 642305, an unusual diastereoselection during the key RCM reaction, resulted in the synthesis of the 11-epi-isorner of Sch 642305. (c) 2005 Published by Elsevier Ltd.