(R)-2-((S)-3-oxo-1,3-diphenylpropyl)-cyclopentanone | 1221402-50-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (R)-2-((S)-3-oxo-1,3-diphenylpropyl)-cyclopentanone
• 英文别名: (R)-2-((S)-3-oxo-1,3-diphenylpropyl)cyclopentanone；(R)-2-[(S)-3-oxo-1,3-diphenylpropyl]cyclopentanone；2-((1S)-3-oxo-1,3-diphenylpropyl)cyclopentanone；2-(3-oxo-1,3-diphenylpropyl)cyclopentanone；(2R)-2-[(1S)-3-oxo-1,3-diphenylpropyl]cyclopentan-1-one
• CAS: 1221402-50-1
• 化学式: C₂₀H₂₀O₂
• 分子量: 292.378
• InChiKey: IQTCJKVODXEBPC-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯亚甲基苯乙酮 、 环戊酮 在 己二酸 、 (1R,2R)-1,2-diaminocyclohexane 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 144.0h， 生成 (R)-2-((S)-3-oxo-1,3-diphenylpropyl)-cyclopentanone 、 (S)-2-[(S)-3-oxo-1,3-diphenylpropyl]cyclopentanone
  参考文献：
  名称：

  Highly enantioselective Michael addition of cyclopentanone with chalcones via novel di-iminium mechanism

  摘要：

  高效的不对称迈克尔加成反应中，环戊酮与香豆素在一种简单且可商购的手性1,2-二氨基环己烷-己二酸的催化下进行，表现出良好的产率（最高可达92%）和优异的对映选择性（最高可达99% ee）。提出了一种新的双阳离子机制用于该反应。

  DOI：

  10.1039/b915852a

文献信息

• C2-symmetric proline-derived tetraamine as highly effective catalyst for direct asymmetric Michael addition of ketones to chalcones
  作者：Shijun Ma、Lulu Wu、Ming Liu、Yongmei Wang

  DOI：10.1039/c2ob06897d

  日期：——

  A C2-symmetric tetraamine catalyst was developed for the asymmetric Michael addition of ketones to chalcones. The corresponding adducts 1,5-dicarbonyl compounds were obtained in good chemical yields with high levels of diastereo- and enantioselectivities (up to >99 : 1 dr and 93% ee) under mild conditions. By studying the ESI-MS of the intermediates, a proposed mechanism was disclosed.

  开发了一种C 2对称四胺催化剂，用于将酮不对称地添加到查耳酮。在温和条件下，以良好的化学收率获得了相应的加合物1,5-二羰基化合物，具有很高的非对映选择性和对映选择性（高达> 99：1 dr和93％ee）。通过研究中间体的ESI-MS，公开了一种提出的机制。
• Direct Asymmetric Michael Additions of Ketones to Nitroolefins and Chalcones Catalyzed by a Chiral C2-Symmetric Pyrrolidine-based Tetraamine
  作者：Shijun Ma、Lulu Wu、Ming Liu、Yongmei Wang

  DOI：10.1002/cjoc.201200214

  日期：2012.8.14

  C2‐Symmetric pyrrolidine‐based tetraamine, available from commercially starting materials, showed good catalytic activity for asymmetric Michael additions of ketones to nitroalkenes especially to chalcones. The reactions proceeded to give the corresponding products in good yields and in a highly selective manner.

  C 2对称的基于吡咯烷的四胺（可从商业原料获得）显示出良好的催化活性，可将酮不​​对称地迈克尔加成至硝基烯烃，特别是对查耳酮。反应进行以高收率和高度选择性的方式得到相应的产物。
• Asymmetric Michael Addition of Cyclohexanone or Cyclopentanone to Chalcones Catalyzed by an<scp>L</scp>-Proline-Based Organic Phosphane
  作者：Lingyan Liu、Yunna Zhu、Kaimeng Huang、Weixing Chang、Jing Li

  DOI：10.1002/ejoc.201201609

  日期：2013.5

  An organophosphane catalyst derived from L-proline was shown to be a very effective catalyst for asymmetric Michael addition reactions of various chalcones to cyclic ketones including both cyclohexanone and cyclopentanone. The corresponding adducts could be obtained in high yields (up to 91 %) and with excellent enantioselectivities (up to 99 % ee) and diastereomeric ratios (up to >99:1). A possible

  来自 L-脯氨酸的有机膦催化剂被证明是一种非常有效的催化剂，用于各种查耳酮与环酮（包括环己酮和环戊酮）的不对称迈克尔加成反应。相应的加合物可以以高产率（高达 91%）和出色的对映选择性（高达 99%ee）和非对映体比率（高达 >99:1）获得。已经提出了基于 31 P NMR 和 ESI-MS 观察的可能的催化机制，用于这种有机膦催化的迈克尔加成。
• Thiophosphoramide catalyzed asymmetric Michael addition of cyclopentanone to chalcones
  作者：Yunfeng Liu、Yang Wu、Aidang Lu、Youming Wang、Guiping Wu、Zhenghong Zhou、Chuchi Tang

  DOI：10.1016/j.tetasy.2011.02.015

  日期：2011.2

  Thiophosphoramide 1b was found to be an effective bifunctional organocatalyst in the asymmetric Michael reaction of cyclopentanone to various chalcones, affording the corresponding adducts in satisfactory yields with moderate to excellent diastereo- (up to 90/10 dr) and enantioselectivities (up to 92% ee).

  在环戊酮与各种查耳酮的不对称迈克尔反应中，硫代磷酰胺1b被发现是一种有效的双功能有机催化剂，以令人满意的产率提供了相应的加合物，具有中等至优异的非对映体（高达90/10 dr）和对映选择性（高达92％ee） ）。
• Pyrrolidine–pyridine base catalysts for the enantioselective Michael addition of ketones to chalcones
  作者：Da-Zhen Xu、Sen Shi、Yingjun Liu、Yongmei Wang

  DOI：10.1016/j.tet.2009.09.001

  日期：2009.11

  A series of pyrrolidine-pyridine base organocatalysts have been developed and 3a found to be a highly effective catalyst for the asymmetric Michael addition reactions of ketones to chalcones. The reaction generated the corresponding products 1, 5-diketones in excellent diastereoselectivities (up to >99:1 dr) and enantioselectivities (up to 100% ee). (c) 2009 Elsevier Ltd. All rights reserved.