(2aS,2bR,5aS,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2a,4,4-trimethyl-octahydro-cyclobuta[a]pentalene-6a-carboxylic acid ethyl ester | 863714-75-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2aS,2bR,5aS,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2a,4,4-trimethyl-octahydro-cyclobuta[a]pentalene-6a-carboxylic acid ethyl ester
• 英文别名: ethyl (1R,2S,5R,6R,7S)-6-[tert-butyl(dimethyl)silyl]oxy-2,9,9-trimethyltricyclo[5.3.0.02,5]decane-5-carboxylate
• CAS: 863714-75-4
• 化学式: C₂₂H₄₀O₃Si
• 分子量: 380.643
• InChiKey: DHTILVFYBGBDCU-YGLRMMQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2aS,2bR,5aS,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2a,4,4-trimethyl-octahydro-cyclobuta[a]pentalene-6a-carboxylic acid ethyl ester 在 碳酸氢钠 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 1-[(2aS,2bR,5aS,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2a,4,4-trimethyl-octahydro-cyclobuta[a]pentalen-6a-yl]-2-triethylsilanyloxy-ethanone
  参考文献：
  名称：

  Synthesis of (+)-Sulcatine G

  摘要：

  The total synthesis of (+)-sulcatine G is described. A key structural feature of sulcatine G is the highly functionalized, enantiomerically pure cyclobutane ring. We have prepared (+)-sulcatine G using a new strategy for bicyclic ring construction, Rh-mediated intramolecular C-H insertion followed by intramolecular alkylation.

  DOI：

  10.1021/jo0508752
• 作为产物：
  描述：

  ethyl (1'R,2'S,5'R,6'R,7'S)-6'-[tert-butyl(dimethyl)silyl]oxy-2'-methylspiro[cyclopropane-1,9'-tricyclo[5.3.0.02,5]decane]-5'-carboxylate 在 platinum(IV) oxide 氢气 、 sodium acetate 、 溶剂黄146 作用下， 以95%的产率得到(2aS,2bR,5aS,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2a,4,4-trimethyl-octahydro-cyclobuta[a]pentalene-6a-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of (+)-Sulcatine G

  摘要：

  The total synthesis of (+)-sulcatine G is described. A key structural feature of sulcatine G is the highly functionalized, enantiomerically pure cyclobutane ring. We have prepared (+)-sulcatine G using a new strategy for bicyclic ring construction, Rh-mediated intramolecular C-H insertion followed by intramolecular alkylation.

  DOI：

  10.1021/jo0508752

文献信息

• Synthesis of (+)-Sulcatine G
  作者：Douglass F. Taber、Kevin J. Frankowski

  DOI：10.1021/jo0508752

  日期：2005.8.1

  The total synthesis of (+)-sulcatine G is described. A key structural feature of sulcatine G is the highly functionalized, enantiomerically pure cyclobutane ring. We have prepared (+)-sulcatine G using a new strategy for bicyclic ring construction, Rh-mediated intramolecular C-H insertion followed by intramolecular alkylation.