(1R*,3R*,8S*,9S*)-3-(tert-butyldimethylsilyloxy)-5,6,13-trimethyl-15-oxatetracyclo[7.5.1.0^1,11.0^3,8]pentadeca-5,10,12-trien-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1R*,3R*,8S*,9S*)-3-(tert-butyldimethylsilyloxy)-5,6,13-trimethyl-15-oxatetracyclo[7.5.1.0^1,11.0^3,8]pentadeca-5,10,12-trien-2-one
• 英文别名: (1R,3R,8S,9S)-3-[tert-butyl(dimethyl)silyl]oxy-5,6,13-trimethyl-15-oxatetracyclo[7.5.1.01,11.03,8]pentadeca-5,10,12-trien-2-one
• 化学式: C₂₃H₃₄O₃Si
• 分子量: 386.607
• InChiKey: GXDWTFCWBNRESU-BZRIBIQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  叔丁基锂 、 (1R*,3R*,8S*,9S*)-3-(tert-butyldimethylsilyloxy)-5,6,13-trimethyl-15-oxatetracyclo[7.5.1.0^1,11.0^3,8]pentadeca-5,10,12-trien-2-one 以 乙醚 、 正戊烷 为溶剂， 反应 0.08h， 以79%的产率得到(1R*,7S*,8S*,9S*,14R*)-7-tert-butyl-14-(tert-butyldimethylsilyloxy)-4,11,12-trimethyl-15-oxatetracyclo[6.6.1.0^2,6.0^9,14]pentadeca-2(6),4,11-trien-1-ol
  参考文献：
  名称：

  Unmasking the 6,7,5-Tricarbocyclic Frame of [5 + 2]/[4 + 2] Pyrone−Alkene Cycloadducts

  摘要：

  Opening of the bridging ether of 8-oxabicyclo[3.2.1]oct-6-ene systems 1,7-fused to a five-membered carbocycle that bears a double bond conjugated to that of the oxabicycle can be induced at low temperaure by the addition of an organolithium reagent. If this double bond is unsubstituted, the opening occurs via an anti-1,6-addition pathway, and if substituted it takes place by means of a more classical syn SN2' addition.

  DOI：

  10.1021/jo9917893
• 作为产物：
  描述：

  3-(tert-butyldimethylsilyloxy)-2-[2,2-bis(phenylsulfonyl)-4-pentynyl]-4H-4-pyranone 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 12.25h， 生成 (1R*,3R*,8S*,9S*)-3-(tert-butyldimethylsilyloxy)-5,6,13-trimethyl-15-oxatetracyclo[7.5.1.0^1,11.0^3,8]pentadeca-5,10,12-trien-2-one
  参考文献：
  名称：

  Unmasking the 6,7,5-Tricarbocyclic Frame of [5 + 2]/[4 + 2] Pyrone−Alkene Cycloadducts

  摘要：

  Opening of the bridging ether of 8-oxabicyclo[3.2.1]oct-6-ene systems 1,7-fused to a five-membered carbocycle that bears a double bond conjugated to that of the oxabicycle can be induced at low temperaure by the addition of an organolithium reagent. If this double bond is unsubstituted, the opening occurs via an anti-1,6-addition pathway, and if substituted it takes place by means of a more classical syn SN2' addition.

  DOI：

  10.1021/jo9917893

文献信息

• Unmasking the 6,7,5-Tricarbocyclic Frame of [5 + 2]/[4 + 2] Pyrone−Alkene Cycloadducts
  作者：J. Ramón Rodríguez、Luis Castedo、José L. Mascareñas

  DOI：10.1021/jo9917893

  日期：2000.4.1

  Opening of the bridging ether of 8-oxabicyclo[3.2.1]oct-6-ene systems 1,7-fused to a five-membered carbocycle that bears a double bond conjugated to that of the oxabicycle can be induced at low temperaure by the addition of an organolithium reagent. If this double bond is unsubstituted, the opening occurs via an anti-1,6-addition pathway, and if substituted it takes place by means of a more classical syn SN2' addition.