(2S)-2-((R)-3-(4-nitrophenyl)-3-oxo-1-phenylpropyl)cyclohexanone | 1198082-63-1

• 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: (2S)-2-((R)-3-(4-nitrophenyl)-3-oxo-1-phenylpropyl)cyclohexanone
• 英文别名: (S)-2-((R)-3-(4-nitrophenyl)-3-oxo-1-phenylpropyl)-cyclohexanone；(S)-2-((R)-3-(4-nitrophenyl)-3-oxo-1-phenylpropyl)cyclohexanone；2-[3-(4-nitrophenyl)-3-oxo-1-phenylpropyl]cyclohexanone；(2S)-2-[(1R)-3-(4-nitrophenyl)-3-oxo-1-phenylpropyl]cyclohexan-1-one
• CAS: 1198082-63-1
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: DJNOYWAFNBXYMI-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-nitro-phenyl)-3-phenyl-propenone 、 环己酮 在 (S)-2-((diphenylphosphoryl)methyl)pyrrolidine 、 苯甲酸 作用下， 以 异丙醇 为溶剂， 反应 72.08h， 以60%的产率得到(2S)-2-((R)-3-(4-nitrophenyl)-3-oxo-1-phenylpropyl)cyclohexanone
  参考文献：
  名称：

  L-脯氨酸基有机磷烷催化环己酮或环戊酮与查耳酮的不对称迈克尔加成反应

  摘要：

  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。

  DOI：

  10.1002/ejoc.201201609

文献信息

• Highly enantioselective Michael addition of cyclic ketones to chalcones catalyzed by pyrrolidine-based imides
  作者：Hong-Yu Xie、Shu-Rong Ban、Ju-Na Liu、Qing-Shan Li

  DOI：10.1016/j.tetlet.2012.05.106

  日期：2012.7

  An efficient procedure for asymmetric Michael addition reaction of cyclic ketones with low activated chalcones catalyzed by pyrrolidine-based phthalimide and 1,8-Naphthalimide catalysts was developed. The corresponding products were obtained in high yields with high diastereoselectivities (up to 99:1 dr) and high enantioselectivities (up to 96% ee) under mild conditions.

  研究了吡咯烷基邻苯二甲酰亚胺和1,8-萘二甲酰亚胺催化剂催化环状酮与低活化查耳酮不对称迈克尔加成反应的有效方法。在温和条件下，以高收率获得了具有高非对映选择性（高达99：1 dr）和高对映选择性（高达96％ee）的相应产品。
• A chiral benzoylthiourea–pyrrolidine catalyst for the highly enantioselective Michael addition of ketones to chalcones
  作者：Shu-rong Ban、Xi-xia Zhu、Zhi-ping Zhang、Qing-shan Li

  DOI：10.1016/j.bmcl.2014.04.005

  日期：2014.6

  A benzoylthiourea–pyrrolidine catalyst was developed for the asymmetric Michael addition of ketones to chalcones. The corresponding products were obtained in high yields with high level of diastereoselectivities (up to 99:1 dr) and high level of enantioselectivities (up to 94% ee) under mild conditions.

  已开发出苯甲酰硫脲-吡咯烷催化剂，用于将酮不对称地迈克尔加成至查耳酮。在温和条件下，以高收率获得了高产率的非对映异构体选择性（高达99：1 dr）和高对映选择性（对映体高达94％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.
• Direct asymmetric Michael addition of ketones to chalcones catalyzed by a hydroxyphthalimide derived triazole–pyrrolidine
  作者：Togapur Pavan Kumar、Mohammad Abdul Sattar、Vanka Uma Maheshwara Sarma

  DOI：10.1016/j.tetasy.2013.11.002

  日期：2013.12

  An efficient protocol for the enantioselective Michael additions of ketones to chalcones catalyzed by a hydroxyphthalimide linked triazole-pyrrolidine derivative has been developed. The corresponding products, 1,5-dicarbonyl compounds, were obtained in good yields with high levels of stereoselectivities under mild reaction conditions employing benzoic acid as an additive. (C) 2013 Elsevier Ltd. All rights reserved.
• 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。