1-trimethoxysilyloxy-2-methylcyclohexene | 1043582-59-7

• 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: 1-trimethoxysilyloxy-2-methylcyclohexene
• 英文别名: 2-methyl-1-(trimethoxysilyloxy)cyclohexene；Trimethyl (2-methylcyclohexen-1-yl) silicate
• CAS: 1043582-59-7
• 化学式: C₁₀H₂₀O₄Si
• 分子量: 232.352
• InChiKey: RFYFWJURAJDPBC-UHFFFAOYSA-N

物化性质

• 沸点：
  107-110 °C(Press: 10 Torr)
• 密度：
  1.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-trimethoxysilyloxy-2-methylcyclohexene 在 4-二甲氨基吡啶 、 (R)-3,3'-dichloro-1,1'-binaphthalene-2,2'-diol lithium salt 、 水 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-[(benzoyloxy)phenylmethyl]-2-methylcyclohexanone
  参考文献：
  名称：

  Construction of quaternary carbon centers by a base-catalyzed enantioselective aldol reaction and related reactions of trimethoxysilyl enol ethers

  摘要：

  The aldol reactions of trimethoxysilyl enol ethers catalyzed by lithium binaphtholate were found to be powerful tools for the construction of quaternary asymmetric carbon centers. The stereoselectivities were greatly affected by the presence of water. Trimethoxysilyl enol ether derived from a cyclic ketone, such as cyclohexanone, was used as a substrate to obtain the anti-adduct preferentially under anhydrous conditions; by contrast, the syn-adduct was preferentially obtained under aqueous conditions with high stereoselectivity. The aldol-Tishchenko reaction of a trimethoxysilyl enol ether derived from acyclic ketones proceeded to give monoacyl 1,3-diol derivatives in high enantioselectivities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.096
• 作为产物：
  描述：

  烯丙基三甲氧基硅烷 、 2-甲基环己酮 在 三氟甲磺酸 、 四丁基碘化铵 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 3.5h， 以73%的产率得到1-trimethoxysilyloxy-2-methylcyclohexene
  参考文献：
  名称：

  Enantioselective construction of quaternary asymmetric carbon centers using an aldol reaction of trimethoxysilyl enol ethers catalyzed by lithium binaphtholate

  摘要：

  An aldol reaction of 2,2-disubstituted trimethoxysilyl enol ethers with alclehydes catalyzed by a dilithium salt of (R)-3,3'-dichlorobinaphthol afforded the corresponding aldol adducts with quaternary carbon centers in high anti-selectivities (syn:anti = similar to 4:50) and enantioselectivities (similar to 90% ee). (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.004

文献信息

• Construction of quaternary carbon centers by a base-catalyzed enantioselective aldol reaction and related reactions of trimethoxysilyl enol ethers
  作者：Tomonori Ichibakase、Tetsuya Kaneko、Yuya Orito、Shunsuke Kotani、Makoto Nakajima

  DOI：10.1016/j.tet.2012.03.096

  日期：2012.6

  The aldol reactions of trimethoxysilyl enol ethers catalyzed by lithium binaphtholate were found to be powerful tools for the construction of quaternary asymmetric carbon centers. The stereoselectivities were greatly affected by the presence of water. Trimethoxysilyl enol ether derived from a cyclic ketone, such as cyclohexanone, was used as a substrate to obtain the anti-adduct preferentially under anhydrous conditions; by contrast, the syn-adduct was preferentially obtained under aqueous conditions with high stereoselectivity. The aldol-Tishchenko reaction of a trimethoxysilyl enol ether derived from acyclic ketones proceeded to give monoacyl 1,3-diol derivatives in high enantioselectivities. (C) 2012 Elsevier Ltd. All rights reserved.
• Enantioselective construction of quaternary asymmetric carbon centers using an aldol reaction of trimethoxysilyl enol ethers catalyzed by lithium binaphtholate
  作者：Tomonori Ichibakase、Yuya Orito、Makoto Nakajima

  DOI：10.1016/j.tetlet.2008.05.004

  日期：2008.7

  An aldol reaction of 2,2-disubstituted trimethoxysilyl enol ethers with alclehydes catalyzed by a dilithium salt of (R)-3,3'-dichlorobinaphthol afforded the corresponding aldol adducts with quaternary carbon centers in high anti-selectivities (syn:anti = similar to 4:50) and enantioselectivities (similar to 90% ee). (c) 2008 Elsevier Ltd. All rights reserved.