2-[(R)-cyclopentyl(hydroxy)methyl]cyclopent-2-en-1-one | 1058143-78-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(R)-cyclopentyl(hydroxy)methyl]cyclopent-2-en-1-one
• CAS: 1058143-78-4
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: IUSYYRPLXPFKNK-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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 、 环戊基甲醛 在 4-二甲氨基吡啶 、 4 A molecular sieve 作用下， 反应 48.0h， 生成 2-[(R)-cyclopentyl(hydroxy)methyl]cyclopent-2-en-1-one 、
  参考文献：
  名称：

  Thiourea-catalyzed Morita–Baylis–Hillman reaction

  摘要：

  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.

  DOI：

  10.1016/j.tet.2008.07.087

文献信息

• 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.