(S)-3-cyclohexylcyclopentanone | 10264-57-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-cyclohexylcyclopentanone
• 英文别名: (3S)-3-cyclohexylcyclopentan-1-one
• CAS: 10264-57-0；145100-68-1；145100-67-0
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: ZKWXHMQLBLFZHP-JTQLQIEISA-N

物化性质

• 沸点：
  126 °C
• 密度：
  0.9730 g/cm3(Temp: 19 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1,2-二苯基乙二胺 、 (S)-3-cyclohexylcyclopentanone 生成 (2R,3R,7S)-7-Cyclohexyl-2,3-diphenyl-1,4-diaza-spiro[4.4]nonane
  参考文献：
  名称：

  Highly Diastereoselective Intermolecular β-Addition of Alkyl Radicals to Chiral 2-(Arylsulfinyl)-2-cycloalkenones

  摘要：

  The diastereoselectivity of intermolecular beta-addition of alkyl radicals to 2-(arylsulfinyl)-acycloalkenones depends largely upon the structure of the arylsulfinyl group. The reaction of a-cyclopentenones or 2-cyclohexenones having a sterically bulky arylsulfinyl group such as (3,5-di-tert-butyl-4-methoxyphenyl)-sulfinyl, (2,4,6-triisopropylphenyl)sulfinyl or (2,4,6-trimethylphenyl)-sulfinyl group gives 3-alkyl-2-(arylsulfinyl)-1-cyclopentanones or 3-alkyl-2-(arylsulfinyl)-1-cyclohexanones in excellent yields and with high diastereoselectivity. Both the X-ray crystallographic analysis and the NOE experiment in the H-1 NMR spectrum of (S)-2-[(2,4,6-triisopropylphenyl)-sulfinyl]- and (S)-2-[(2,4,6-trimethylphenyl)sulfinyl]-2-cyclopentenone reveal an effective shielding of one of the olefin faces at the beta-position by o-isopropyl and o-methyl groups. The addition of bidentate Lewis acids reverses the stereoselection through chelating the intermediates to give the addition products with high diastereoselectivity.

  DOI：

  10.1021/jo971093e
• 作为产物：
  描述：

  3-cyclohexylcyclopent-2-en-1-one 在 C₂HF₃O₂*C₁₆H₁₈N₂O₂ 二氢吡啶 作用下， 以 乙醚 为溶剂， 反应 8.0h， 以85%的产率得到(S)-3-cyclohexylcyclopentanone
  参考文献：
  名称：

  Hydride reduction of alpha, beta-unsaturated carbonyl compounds using chiral organic catalysts

  摘要：

  非金属手性有机催化剂被用于催化α，β-不饱和羰基化合物的1,4-氢化物还原。α，β-不饱和羰基化合物可以是醛或环酮，氢化物供体可以是二氢吡啶。该反应是对映选择性的，并且可以使用多种氢化物供体、催化剂和底物进行。该发明还提供了用于进行α，β-不饱和羰基化合物的1,4-氢化物加成的有效组合物。

  公开号：

  US20060161024A1

文献信息

• Catalytic Enantioselective Conjugate Addition of Grignard Reagents to Cyclic Enones Using<i>C</i>₁-1,1′-Bisisoquinoline-Based Chiral Ligands
  作者：Gao Qi、Zaher M. A. Judeh

  DOI：10.1080/00397911.2010.541969

  日期：2012.6

  Abstract New highly constrained chiral C 1-1,1′-bisisoquinoline ligands were examined in the enantioselective conjugate addition of Grignard reagents to cyclohexenone and cyclopentenone. The desired 1,4-adducts were obtained in excellent yield and moderate enantiomeric excess (up to 35%). GRAPHICAL ABSTRACT

  摘要 在格氏试剂与环己烯酮和环戊烯酮的对映选择性共轭加成中，研究了新的高度受限的手性 C 1-1,1'-双异喹啉配体。以极好的收率和适度的对映体过量（高达 35%）获得了所需的 1,4-加合物。图形概要
• Asymmetric Catalysis. Asymmetric Catalytic Intramolecular Hydroacylation of 4-Pentenals Using Chiral Rhodium Diphosphine Catalysts
  作者：Richard W. Barnhart、Xianqi Wang、Pedro Noheda、Steven H. Bergens、John Whelan、B. Bosnich

  DOI：10.1021/ja00084a025

  日期：1994.3

  Catalysts of the type [Rh(chiral diphosphine)] + convert 4-substituted 4-pentenals into the corresponding 3-substituted cyclopentanones with generally high turnover numbers and frequencies at 25 o C. The enantioselectivities of various substituted 4-pentenals with two chiral diphosphines have been explored. It was found that with the binap catalyst, almost complete enantioselectivity is observed for

  [Rh(手性二膦)] + 类型的催化剂在 25 o C 下将 4-取代的 4-戊烯醛转化为相应的 3-取代的环戊酮，其转换数和频率通常很高。 具有两个手性二膦的各种取代的 4-戊烯醛的对映选择性已被探索。发现使用 binap 催化剂，对于带有 4-取代叔取代基的 4-戊烯醛底物和酯基，观察到几乎完全的对映选择性。酮取代基具有非常高的对映选择性
• Organocatalytic Transfer Hydrogenation of Cyclic Enones
  作者：Jamison B. Tuttle、Stéphane G. Ouellet、David W. C. MacMillan

  DOI：10.1021/ja0653066

  日期：2006.10.1

  The first enantioselective organocatalytic transfer hydrogenation of cyclic enones has been accomplished. The use of iminium catalysis has provided a new organocatalytic strategy for the enantioselective reduction of beta,beta-substituted alpha,beta-unsaturated cycloalkenones, to generate beta-stereogenic cyclic ketones. The use of imidazolidinone 4 as the asymmetric catalyst has been found to mediate

  环烯酮的第一个对映选择性有机催化转移氢化已经完成。亚胺催化的使用为β,β-取代的α,β-不饱和环烯酮的对映选择性还原提供了一种新的有机催化策略，以生成β-立体环酮。已发现使用咪唑烷酮 4 作为不对称催化剂可介导大量烯酮底物与叔丁基 Hantzsch 酯作为廉价氢源的氢化。催化剂 4 使环烯酮对映选择性转移氢化的能力已扩展到五、六和七元环系统。
• Asymmetric catalytic intramolecular hydroacylation of 4-substituted pent-4-enals to β-substituted cyclopentanones
  作者：Richard W. Barnhart、David A. McMorran、B. Bosnich

  DOI：10.1039/a700076f

  日期：——

  The catalyst, [Rh(S,S-Me-duphos)(acetone) 2 ] + , rapidly and efficiently converts 4-substituted pent-4-enals bearing primary and secondary substituents to the corresponding cyclopentanones and for a variety of substituents the ee was found to range from 93 to 96% at 25 °C.

  催化剂[Rh(S,S-Me-duphos)(丙酮) 2 ] + 能快速、高效地将带有一级和二级取代基的 4-取代戊-4-烯烃转化为相应的环戊酮。
• Highly enantioselective cyclization using cationic Rh(I) with chiral ligand
  作者：Xiao-Ming Wu、Kazuhisa Funakoshi、Kiyoshi Sakai

  DOI：10.1016/s0040-4039(00)60966-8

  日期：1992.10

  (>99% de) of 3R (or S) 3,4-disubstituted 4-pentenals into the corresponding 3,4-cis(or trans)-disubstituted cyclopentanone and highly enantioselective cyclization (>99% ee) of 4-substituted 4-pentenals into 3-substituted cyclopentanone were achieved by using cationic Rh+(BINAP)ClO4−.

  3R（或S）3,4-二取代的4-戊烯的非对映选择性环化（> 99％de）转化为相应的3,4-顺（或反式）-二取代的环戊酮和4的高度对映选择性环化（> 99％ee） -取代的4-戊烯醛为3-取代环戊酮通过使用阳离子铑达到+（BINAP）CLO 4 - 。