2-[(R)-cyclohexyl(hydroxy)methyl]cyclopent-2-en-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(R)-cyclohexyl(hydroxy)methyl]cyclopent-2-en-1-one
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: DSPVFOSPZJSVTN-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  2-环戊烯酮 、 环己烷基甲醛 在 (R)-(+)-4-dimethylaminopyrindinyl(pentaphenylcyclo-pentadienyl)iron 、 magnesium iodide 作用下， 以 异丙醇 为溶剂， 反应 48.0h， 生成 2-[(R)-cyclohexyl(hydroxy)methyl]cyclopent-2-en-1-one 、 2-[(S)-cyclohexyl(hydroxy)methyl]cyclopent-2-en-1-one
  参考文献：
  名称：

  利用手性DMAP催化剂，MgI 2促进环戊烯酮的对映选择性森田-贝利斯-希尔曼反应。

  摘要：

  Fu的平面手性DMAP催化剂可在存在MgI（2）作为助催化剂的情况下，有效地促进环戊烯酮与多种醛类的不对称Morita-Baylis-Hillman反应。

  DOI：

  10.1039/c001977a

文献信息

• Enantioselective Morita–Baylis–Hillman (MBH) reaction promoted by a heterobimetallic complex with a Lewis base
  作者：Katsuya Matsui、Shinobu Takizawa、Hiroaki Sasai

  DOI：10.1016/j.tetlet.2004.11.089

  日期：2005.3

  A new double-activation catalysis is presented for the Morita-Baylis-Hillman (MBH) reaction of an alpha,beta-unsaturated ketone and an aldehyde by the combined use of a heterobimetallic asymmetric complex and tributylphosphine ((n-Bu)(3)P) to afford the alpha-methylene-beta-hydroxy ketone with up to 99% ce. (C) 2004 Elsevier Ltd. All rights reserved.
• Thiourea-catalyzed Morita–Baylis–Hillman reaction
  作者：Yoshihiro Sohtome、Nobuko Takemura、Rika Takagi、Yuichi Hashimoto、Kazuo Nagasawa

  DOI：10.1016/j.tet.2008.07.087

  日期：2008.9

  Here, we describe our studies on the thiourea-catalyzed Morita-Baylis-Hillman (MBH) reaction. Chemoselective activation of carbonyl compounds via hydrogen bonding to thiourea as a catalyst is the key to drastic rate acceleration of this reaction. The application of chiral bis-thiourea-type organocatalysts, which can form a chiral double hydrogen-bonding network, is effective for enantioselective MBH reaction. A cooperative system of bis-thiourea compounds, synthesized from 1,2-diaminocyclohexane, and a Lewis base effectively promotes the MBH reaction at lower temperature, affording the MBH adducts in 33-95% yield with 44-90% ee. A plausible transition state model of the enantioselective MBH reaction is presented. (C) 2008 Elsevier Ltd. All rights reserved.