[(1R,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enyl]-acetic acid ethyl ester | 866430-79-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1R,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enyl]-acetic acid ethyl ester
• 英文别名: ethyl 2-[(1R,5R,6R)-6-but-3-enyl-5-[tert-butyl(dimethyl)silyl]oxy-2-oxocyclohex-3-en-1-yl]acetate
• CAS: 866430-79-7
• 化学式: C₂₀H₃₄O₄Si
• 分子量: 366.573
• InChiKey: OWKVHSKKKIZBFJ-JFIYKMOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1R,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enyl]-acetic acid ethyl ester 在 Wilkinson's catalyst 、 Grubbs catalyst first generation 咪唑 、 titanium(IV) isopropylate 、 sodium tetrahydroborate 、 cerium(III) chloride 、 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， -50.0~90.0 ℃ 、101.33 kPa 条件下， 反应 81.0h， 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
• 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 copper(l) iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二苯醚 为溶剂， 反应 0.17h， 生成 [(1R,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enyl]-acetic acid ethyl ester
  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.