[2,2-Dimethyl-4-(trimethylsilylmethyl)cyclohex-3-en-1-yl]methanol | 245670-14-8

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: [2,2-Dimethyl-4-(trimethylsilylmethyl)cyclohex-3-en-1-yl]methanol
• CAS: 245670-14-8
• 化学式: C₁₃H₂₆OSi
• 分子量: 226.434
• InChiKey: ZQLCPNJGENTUAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [2,2-Dimethyl-4-(trimethylsilylmethyl)cyclohex-3-en-1-yl]methanol 在 N-甲基吗啉 、 二氯二甲基硅烷 作用下， 以 乙醚 、 萘烷 为溶剂， 反应 147.0h， 生成 methyl 2-(6,6-dimethyl-8-methylidene-3-oxabicyclo[3.3.1]nonan-2-yl)acetate
  参考文献：
  名称：

  Silicon-Controlled Intramolecular Thermal H-Ene Reaction – A New Access to a Key Intermediate of (±)-cis-γ-Irone

  摘要：

  The primordial influence of the silyl group in an intramolecular thermal H-ene reaction is reported. The silyl group lowered the energy of the transition state and allowed the reaction to proceed at a lower temperature than that of the simple all-carbon analog, thereby excluding the formation of undesirable by-products. This sequence has been applied for new access to a key intermediate in the diastereoselective synthesis of (+/-)-cis-gamma-irone with high chemocontrol and significantly improved overall yield.

  DOI：

  10.1002/(sici)1099-0690(199908)1999:8<1825::aid-ejoc1825>3.0.co;2-5
• 作为产物：
  描述：

  Ethyl 4-diethoxyphosphoryloxy-2,2-dimethylcyclohex-3-ene-1-carboxylate 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 36.5h， 生成 [2,2-Dimethyl-4-(trimethylsilylmethyl)cyclohex-3-en-1-yl]methanol
  参考文献：
  名称：

  Silicon-Controlled Intramolecular Thermal H-Ene Reaction – A New Access to a Key Intermediate of (±)-cis-γ-Irone

  摘要：

  The primordial influence of the silyl group in an intramolecular thermal H-ene reaction is reported. The silyl group lowered the energy of the transition state and allowed the reaction to proceed at a lower temperature than that of the simple all-carbon analog, thereby excluding the formation of undesirable by-products. This sequence has been applied for new access to a key intermediate in the diastereoselective synthesis of (+/-)-cis-gamma-irone with high chemocontrol and significantly improved overall yield.

  DOI：

  10.1002/(sici)1099-0690(199908)1999:8<1825::aid-ejoc1825>3.0.co;2-5

文献信息

• Silicon-Controlled Intramolecular Thermal H-Ene Reaction – A New Access to a Key Intermediate of (±)-cis-γ-Irone
  作者：Honoré Monti、Gilles Laval、Michel Féraud

  DOI：10.1002/(sici)1099-0690(199908)1999:8<1825::aid-ejoc1825>3.0.co;2-5

  日期：1999.8

  The primordial influence of the silyl group in an intramolecular thermal H-ene reaction is reported. The silyl group lowered the energy of the transition state and allowed the reaction to proceed at a lower temperature than that of the simple all-carbon analog, thereby excluding the formation of undesirable by-products. This sequence has been applied for new access to a key intermediate in the diastereoselective synthesis of (+/-)-cis-gamma-irone with high chemocontrol and significantly improved overall yield.