4,4-dimethyl-2-(hydroxy(phenyl)methyl)cyclohexanone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4,4-dimethyl-2-(hydroxy(phenyl)methyl)cyclohexanone
• 英文别名: (2R)-2-[(S)-hydroxy(phenyl)methyl]-4,4-dimethylcyclohexan-1-one
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: LNIIMJKTKLDROD-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醛 、 4,4-二甲基环己酮 在 N-甲基二环己基胺 、 Trichloro(trifluoromethylsulfonyloxy)silane 、 2,2'-双(二苯基氧膦)-1,1'-联萘 作用下， 以 二氯甲烷 、 丙腈 为溶剂， 反应 2.0h， 生成 2-[hydroxy(phenyl)methyl]-4,4-dimethylcyclohexan-1-one 、 4,4-dimethyl-2-(hydroxy(phenyl)methyl)cyclohexanone 、 4,4-dimethyl-2-(hydroxy(phenyl)methyl)cyclohexanone
  参考文献：
  名称：

  Trichlorosilyl triflate for enantioselective direct-type aldol reaction with chiral phosphine oxide

  摘要：

  Trichlorosilyl triflate, in the presence of a chiral Lewis base catalyst, provides an effective method for the enantioselective direct-type aldol reaction of aldehydes and ketones. A chiral Lewis base induces both the production and activation of trichlorosilyl enol ether, yielding an aldol product in good yield and with high diastereo- and enantioselectivities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.095

文献信息

• Novel enantioselective direct aldol-type reaction promoted by a chiral phosphine oxide as an organocatalyst
  作者：Shunsuke Kotani、Yasushi Shimoda、Masaharu Sugiura、Makoto Nakajima

  DOI：10.1016/j.tetlet.2009.05.065

  日期：2009.8

  Chiral phosphine oxide successfully catalyzed the direct aldol-type reactions of cyclohexanone derivatives and benzaldehyde derivatives in high stereoselectivities. The reaction mechanism involves the in situ formation of trichlorosilyl enol ethers. The present reaction could be extended to the cross-aldol reactions between two aldehydes.

  手性氧化膦以高的立体选择性成功催化了环己酮衍生物和苯甲醛衍生物的直接羟醛型反应。反应机理涉及三氯甲硅烷基烯醇醚的原位形成。本反应可以扩展到两个醛之间的交叉-羟醛反应。
• Trichlorosilyl triflate for enantioselective direct-type aldol reaction with chiral phosphine oxide
  作者：Shunsuke Kotani、Shohei Aoki、Masaharu Sugiura、Makoto Nakajima

  DOI：10.1016/j.tetlet.2011.03.095

  日期：2011.6

  Trichlorosilyl triflate, in the presence of a chiral Lewis base catalyst, provides an effective method for the enantioselective direct-type aldol reaction of aldehydes and ketones. A chiral Lewis base induces both the production and activation of trichlorosilyl enol ether, yielding an aldol product in good yield and with high diastereo- and enantioselectivities. (C) 2011 Elsevier Ltd. All rights reserved.