(R)-4-((tert-butyldimethylsilyl)oxy)-5-methylcyclohexa-1,5-dien-1-yl acetate | 1199941-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-4-((tert-butyldimethylsilyl)oxy)-5-methylcyclohexa-1,5-dien-1-yl acetate
• CAS: 1199941-04-2
• 化学式: C₁₅H₂₆O₃Si
• 分子量: 282.455
• InChiKey: GCCKYPABDVTDPV-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (R)-4-((tert-butyldimethylsilyl)oxy)-5-methylcyclohexa-1,5-dien-1-yl acetate 、 3-(Benzenesulfonyl)-1-phenylpyrrole-2,5-dione 以 二氯甲烷 为溶剂， 反应 24.0h， 以83%的产率得到
  参考文献：
  名称：

  Controlling the Facial Selectivity of Asymmetric [4 + 2] Cyclo-additions: A Concise Synthesis of the cis-Decalin Core Structure of Superstolides A and B

  摘要：

  Reglo-, stereo-, and facial selective [4 + 2] cycloadditions between highly activated vinyl sulfones and 1,3-dienes derived from (R)-4-tert-wbutyldimethylsilyloxy-2-cyclohexen-1-one provide a powerful approach for the asymmetric synthesis of compounds containing the bicyclo[2.2.2]octanone carbon skeleton. This new methodology has been successfully applied to the asymmetric synthesis of the cis-decalin core structure of the potent anticancer marine natural products superstolides A and B.

  DOI：

  10.1021/ol201095b
• 作为产物：
  描述：

  乙酸酐 、 (R)-4-[(tert-butyldimethylsilyl)oxy]-3-methyl-cyclohex-2-en-1-one 在 lithium diisopropyl amide 作用下， 以84%的产率得到(R)-4-((tert-butyldimethylsilyl)oxy)-5-methylcyclohexa-1,5-dien-1-yl acetate
  参考文献：
  名称：

  Asymmetric [4+2] cycloadditions employing 1,3-dienes derived from (R)-4-t-butyldimethyl-silyloxy-2-cyclohexen-1-one

  摘要：

  1,3-Dienes derived from (R)-4-t-butyldimethylsilyloxy-2-cyclohexen-1-one react with activated dienophiles to form predominately (or sometimes exclusively) syn/endo products. These controlled [4+2] cycloadditions increase the asymmetric complexity from one asymmetric center in the starting material to five asymmetric centers in the products in a single step, and provide a powerful approach for the asymmetric synthesis of compounds containing the bicyclo[2.2.2]octanone carbon skeleton. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.055