[(4R)-5-butyl-4-[tert-butyl(dimethyl)silyl]oxy-2-methylcyclohexa-1,5-dien-1-yl] acetate | 1199941-06-4

• 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: [(4R)-5-butyl-4-[tert-butyl(dimethyl)silyl]oxy-2-methylcyclohexa-1,5-dien-1-yl] acetate
• CAS: 1199941-06-4
• 化学式: C₁₉H₃₄O₃Si
• 分子量: 338.563
• InChiKey: KXZRAPIWDKPGOS-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 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：

  N-苄基马来酰亚胺 、 [(4R)-5-butyl-4-[tert-butyl(dimethyl)silyl]oxy-2-methylcyclohexa-1,5-dien-1-yl] acetate 以 苯 为溶剂， 反应 96.0h， 以87%的产率得到[(1R,2R,6S,7R,10R)-4-benzyl-1-butyl-10-[tert-butyl(dimethyl)silyl]oxy-7-methyl-3,5-dioxo-4-azatricyclo[5.2.2.02,6]undec-8-en-8-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
• 作为产物：
  描述：

  (4R)-3-n-butyl-4-(t-butyldimethylsilyloxy)-6-methyl-2-cyclohexen-1-one 、 乙酸酐 在 lithium diisopropyl amide 作用下， 以70%的产率得到[(4R)-5-butyl-4-[tert-butyl(dimethyl)silyl]oxy-2-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

文献信息

• Controlling the Facial Selectivity of Asymmetric [4 + 2] Cyclo-additions: A Concise Synthesis of the <i>cis</i>-Decalin Core Structure of Superstolides A and B
  作者：Lei Chen、Zhengmao Hua、Gangqin Li、Zhendong Jin

  DOI：10.1021/ol201095b

  日期：2011.7.15

  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.