(2S)-2-((R)-1-(4-bromophenyl)-3-oxo-3-phenylpropyl)cyclohexanone | 1058744-63-0

• 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)-1-(4-bromophenyl)-3-oxo-3-phenylpropyl)cyclohexanone
• 英文别名: (S)-2-((R)-1-(4-bromophenyl)-3-oxo-3-phenylpropyl)-cyclohexanone；(S)-2-((R)-1-(4-bromophenyl)-3-oxo-3-phenylpropyl)cyclohexanone；2-[1-(4-bromophenyl)-3-oxo-3-phenylpropyl]cyclohexanone；(2S)-2-[(1R)-1-(4-bromophenyl)-3-oxo-3-phenylpropyl]cyclohexan-1-one
• CAS: 1058744-63-0
• 化学式: C₂₁H₂₁BrO₂
• 分子量: 385.301
• InChiKey: CLWWJWZIBORGLN-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 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：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴查尔酮 、 环己酮 在 (S)-1-benzoyl-3-(pyrrolidin-2-ylmethyl)thiourea 、 苯甲酸 作用下， 以 neat (no solvent) 为溶剂， 反应 168.5h， 以88%的产率得到(2S)-2-((R)-1-(4-bromophenyl)-3-oxo-3-phenylpropyl)cyclohexanone
  参考文献：
  名称：

  手性苯甲酰硫脲-吡咯烷催化剂，可将酮高度对映选择性地加成至查耳酮

  摘要：

  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）。

  DOI：

  10.1016/j.bmcl.2014.04.005

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。
• 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）。