3-(2-chlorophenyl)cyclohexan-1-one | 141632-29-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-chlorophenyl)cyclohexan-1-one
• 英文别名: (S)-3-(2-chlorophenyl)cyclohexan-1-one；(S)-3-(2-chlorophenyl)cyclohexanone；(3S)-3-(2-Chlorophenyl)cyclohexanone；(3S)-3-(2-chlorophenyl)cyclohexan-1-one
• CAS: 141632-29-3
• 化学式: C₁₂H₁₃ClO
• 分子量: 208.688
• InChiKey: UEQNZFVVYHRYOX-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 2-氯苯基硼酸 在 chlorobis(ethylene)rhodium(I) dimer 、 (R)-N-[(E)-1,3-diphenylprop-2-enylidene]-tert-butanesulfinamide 、 cesium fluoride 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以91%的产率得到3-(2-chlorophenyl)cyclohexan-1-one
  参考文献：
  名称：

  手性N-叔丁亚磺酰基α，β-不饱和酮亚胺：一种简单且高效的烯烃/亚磺酰亚胺杂配体，可用于不对称的1,4-加成†

  摘要：

  通过α，β-不饱和酮与化合物的简单一步缩合，已经开发出一种新型的手性烯烃/亚磺酰亚胺杂化配体 叔丁烷亚磺酰胺 并成功地用于铑催化的不对称共轭加成中，从而以优异的ee高收率提供所需的加合物。

  DOI：

  10.1039/c1ob05971h

文献信息

• Readily Accessible Chiral Diene Ligands for Rh-Catalyzed Enantioselective Conjugate Additions of Boronic Acids
  作者：Barry M. Trost、Aaron C. Burns、Thomas Tautz

  DOI：10.1021/ol201754c

  日期：2011.9.2

  the broad scope of the Pd-catalyzed asymmetric alkylation of meso- and d,l-divinylethylene carbonate, several chiral diene ligands were prepared in two steps from commercial materials. Subsequently, these ligands were evaluated in the Rh-catalyzed asymmetric conjugate addition of boronic acids to enones.

  由于Pd催化的内消旋和d，1-二乙烯基碳酸亚乙酯的不对称烷基化反应的广泛范围，从商业原料中分两步制备了几种手性二烯配体。随后，在硼酸到烯酮的Rh催化的不对称共轭加成中评估了这些配体。
• Synthesis of Highly Enantioenriched Propelladienes and their Application as Ligands in Asymmetric Rh-Catalyzed 1,4-Additions
  作者：Tommaso Pecchioli、Mathias Christmann

  DOI：10.1021/acs.orglett.8b02204

  日期：2018.9.7

  The first synthesis of highly enantioenriched [4.3.3]propelladienes is reported. The novel bridged bicyclo[3.3.0] dienes were applied as steering ligands in the rhodium-catalyzed asymmetric arylation of cyclic enones. The catalytic system showed high catalytic activity, and the 1,4-adducts were obtained in good to excellent yields (46–99%) with enantioselectivities up to 96% ee.

  据报道，首次合成了高度对映体富集的[4.3.3]丙二烯。新型桥联双环[3.3.0]二烯用作铑催化的环状烯酮的不对称芳基化反应的配位体。催化体系显示出较高的催化活性，并且1,4-加合物以良好至优异的收率（46–99％）获得，对映选择性高达ee的96％。
• Simple Chiral Chain Dienes as Ligands for Rh(I)-Catalyzed Conjugated Additions
  作者：Xichao Hu、Minyang Zhuang、Ziping Cao、Haifeng Du

  DOI：10.1021/ol901949n

  日期：2009.10.15

  This paper describes that a simple and readily available chain diene (3R,4R)-hexa-1,5-diene-3,4-diol (L1) was successfully utilized as a novel steering ligand for Rh(I)-catalyzed asymmetric conjugated additions. Encouraging yields and ee’s have been achieved, which may provide a new and practical direction for designing chiral diene ligands in the future.

  本文描述了一种简单易用的链二烯（3 R，4 R）-六-1,5-二烯-3,4-二醇（L1）已成功用作Rh（I）催化的新型操纵配体不对称共轭加成。已经实现了令人鼓舞的产率和ee，这可能为将来设计手性二烯配体提供新的实用方向。
• 4,8-Disubstituted Bicyclo[3.3.1]nona-2,6-dienes as Chiral Ligands for Rh-Catalyzed Asymmetric 1,4-Addition Reactions
  作者：Renaldas Rimkus、Marius Jurgelėnas、Sigitas Stončius

  DOI：10.1002/ejoc.201500202

  日期：2015.5

  C2-symmetric chiral diene ligands based on 4,8-endo,endo-disubstituted bicyclo[3.3.1]nona-2,6-diene framework have been designed and synthesized. The rhodium complexes of the dienes, which were obtained in a few straightforward steps from enantiomerically pure bicyclo[3.3.1]nonane-2,6-dione, exhibited excellent catalytic activity and high enantioselectivity (up to 96 % ee) in the conjugate addition

  设计并合成了基于 4,8-endo,endo-di 取代双环 [3.3.1]nona-2,6-diene 骨架的 C2 对称手性二烯配体。二烯的铑配合物是从对映体纯的双环[3.3.1]壬烷-2,6-二酮通过几个简单的步骤获得的，在共轭加成中表现出优异的催化活性和高对映选择性（高达 96% ee）芳基硼酸在温和的反应条件下以高原子效率反应成环烯酮。
• Vicinal-Diamine-Based Chiral Chain Dienes as Ligands for Rhodium(I)-Catalyzed Highly Enantioselective Conjugated Additions
  作者：Yazhou Wang、Xichao Hu、Haifeng Du

  DOI：10.1021/ol1023536

  日期：2010.12.3

  A variety of readily accessible vicinal-diamine-based chiral chain dienes were successfully synthesized and utilized as steering ligands for rhodium-catalyzed conjugated additions of organoboronic acids to α,β-unsaturated carbonyl compounds to afford the desired adducts in good to excellent yields and ee’s.

  成功地合成了多种容易获得的基于邻二胺的手性链二烯，并将其用作有机硼酸与α，β-不饱和羰基化合物进行铑催化共轭加成反应的配位体，从而以良好的产率和优异的收率提供了所需的加合物。 。