3-(2-phenylethyl)cyclopentanone | 106988-14-1

• 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-phenylethyl)cyclopentanone
• 英文别名: 3-phenethylcyclopentanone；3-(2-Phenylethyl)cyclopentan-1-one
• CAS: 106988-14-1
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: FWVFOIWKPZFNAB-UHFFFAOYSA-N

物化性质

• 沸点：
  85 °C(Press: 0.08 Torr)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  3-(2-phenylethyl)cyclopentanone 生成 2,3,3a,4,5,9b-Hexahydro-1H-benzoindene
  参考文献：
  名称：

  MALEK, HASAN;PILLAI, KALEEKKAL, MADHAVAN, RADHAKRISHNA;MUNSHI, KISHAN, LA+

  摘要：

  DOI：
• 作为产物：
  描述：

  3-乙氧基-2-环戊烯酮 在 1,3-bis(2,6-diisopropylphenyl)imidazolium copper(I) chloride sodium t-butanolate 、 poly(methylhydrosiloxane) 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 13.0h， 生成 3-(2-phenylethyl)cyclopentanone
  参考文献：
  名称：

  铜卡宾络合物催化的α，β-不饱和羰基化合物的共轭还原。

  摘要：

  [反应：见正文]制备了N-杂环卡宾氯化铜（NHC-CuCl）配合物（2），并用于催化α，β-不饱和羰基化合物的共轭还原。催化量的2和NaOt-Bu与作为化学计量还原剂的聚（甲基氢硅氧烷）（PMHS）的结合产生了一种活性催化剂，用于1,4-还原三和四取代的α，β-不饱和酯和环状烯酮。活性催化物质也可以在NaOt-Bu和PMHS存在下由1,3-双（2,6-二异丙基苯基）-咪唑鎓氯化物（1）CuCl（2）.2H（2）O原位生成。

  DOI：

  10.1021/ol034560p

文献信息

• METHOD FOR SYNTHESIZING OPTICALLY ACTIVE CARBONYL COMPOUNDS
  申请人：BASF SE

  公开号：US20180057437A1

  公开（公告）日：2018-03-01

  The present invention relates to a process for the preparation of an optically active carbonyl compound by asymmetric hydrogenation of a prochiral α,β-unsaturated carbonyl compound with hydrogen in the presence of at least one optically active transition metal catalyst that is soluble in the reaction mixture and which has rhodium as catalytically active transition metal and a chiral, bidentate bisphosphine ligand, wherein the reaction mixture during the hydrogenation of the prochiral α,β-unsaturated carbonyl compound additionally comprises at least one compound of the general formula (I): in which R 1 , R 2 : are identical or different and are C 6 - to C 10 -aryl which is unsubstituted or carries one or more, e.g. 1, 2, 3, 4 or 5, substituents which are selected from C 1 - to C 6 -alkyl, C 3 - to C 6 -cycloalkyl, C 6 - to C 10 -aryl, C 1 - to C 6 -alkoxy and amino; Z is a group CHR 3 R 4 or aryl which is unsubstituted or carries one or more, e.g. 1, 2, 3, 4 or 5, substituents which are selected from C 1 - to C 6 -alkyl, C 3 - to C 6 -cycloalkyl, C 6 - to C 10 -aryl, C 1 - to C 6 -alkoxy and amino, wherein R 3 and R 4 are as defined in the claims and the description.

  本发明涉及一种通过在至少一种可溶于反应混合物中的光学活性过渡金属催化剂的存在下，将可溶性光学活性过渡金属铑和手性双膦配体作为催化活性过渡金属的α，β-不对称氢化的可半手性α，β-不饱和羰基化合物与氢气反应制备光学活性羰基化合物的方法。在氢化可半手性α，β-不饱和羰基化合物的过程中，反应混合物中还包括至少一种符合一般式（I）的化合物：其中 R1、R2：相同或不同，为未取代或带有一个或多个（例如1、2、3、4或5个）C6到C10芳基取代基的化合物，所述取代基选自C1到C6烷基、C3到C6环烷基、C6到C10芳基、C1到C6烷氧基和氨基；Z是一种基团CHR3R4或未取代或带有一个或多个（例如1、2、3、4或5个）取代基的芳基，所述取代基选自C1到C6烷基、C3到C6环烷基、C6到C10芳基、C1到C6烷氧基和氨基，其中R3和R4如权利要求和说明书中定义。
• Asymmetric 1,4-reductions of and 1,4-additions to enoates and related systems
  申请人：Massachusetts Institute of Technology

  公开号：US06465664B1

  公开（公告）日：2002-10-15

  One aspect of the present invention relates to methods for the transition-metal-catalyzed asymmetric 1,4-addition of a nucleophile, e.g., hydride, to cyclic and acyclic enoates and enones. In certain embodiments of the methods of the present invention, the transition metal catalyst consists essentially of copper and an asymmetric bidentate bisphosphine ligand.

  本发明的一个方面涉及过渡金属催化的不对称1,4-核亲电体（例如氢化物）对环状和非环状烯酸酯和烯醇的加成方法。在本发明的某些实施例中，过渡金属催化剂主要由铜和不对称双膦双膦配体组成。
• Method for the Production of Optically Active Carbonyl
  申请人：Jakel Christoph

  公开号：US20080269528A1

  公开（公告）日：2008-10-30

  The present invention relates to a process for preparing optically active carbonyl compounds by asymmetrically hydrogenating α,β-unsaturated carbonyl compounds in the presence of optically active transition metal catalysts which are soluble in the reaction mixture and have at least one carbon monoxide ligand. The present invention especially relates to a process for preparing optically active aldehydes or ketones, in particular citronellal, by asymmetrically hydrogenating the corresponding optically active α,β-unsaturated aldehydes or ketones.

  本发明涉及一种通过在存在可溶于反应混合物中并具有至少一个一氧化碳配体的光学活性过渡金属催化剂的情况下，对α，β-不饱和羰基化合物进行不对称氢化的方法。本发明特别涉及一种通过对相应的光学活性α，β-不饱和醛或酮进行不对称氢化而制备光学活性醛或酮的方法，特别是柠檬醛。
• Titanocene(II)-promoted reductive alkylation of anilides with thioacetals
  作者：Takeshi Takeda、Yasutaka Yatsumonji、Akira Tsubouchi

  DOI：10.1016/j.tetlet.2005.03.062

  日期：2005.5

  Titanocene(II)-promoted reaction of anilides with thioacetals followed by treatment with a small amount of water gave reductive alkylation products, anilines with a secondary alkyl group.

  钛茂金属（II）促进的苯甲酸酯与硫缩醛的反应，然后用少量水处理，得到还原性烷基化产物，即具有仲烷基的苯胺。
• Lewis Acid Catalysed Asymmetric One-Carbon Ring-Expansion of Prochiral Cyclobutanones
  作者：Johannes M. Wahl、Marius Tenberge

  DOI：10.1055/s-0042-1751386

  日期：2023.3

  Enantioselective methylene insertion into prochiral cyclobutanones is described providing access to chiral β-substituted cyclopentanones as important structural motif in synthesis and natural products. Commercially available trimethylsilyl as well as other silyl diazomethanes act as one-carbon synthon and scandium triflate is found to be a potent Lewis acid catalyst. By using bis(oxazoline) ligands, enantioinduction is achieved for a number of β-substituted cyclopentanones including examples bearing all-carbon quaternary stereocentres.

  摘要：本文描述了手性β-取代环戊酮的亲核亚甲基插入反应，提供了在合成和天然产物中作为重要结构基元的手性β-取代环戊烯酮的访问途径。商业上可获得的三甲基硅基以及其他硅基重氮甲烷作为一碳合成物，而三氟甲基硫酸钪则被发现是一种有效的路易斯酸催化剂。通过使用双噁唑啉配体，实现了对许多β-取代环戊烯酮的对映诱导，包括带有全碳季节立体中心的例子。