2-Phenyl-1-acetylcyclohexene | 72157-48-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-Phenyl-1-acetylcyclohexene
• 英文别名: 1-Acetyl-2-phenylcyclohexen；1-(2-phenylcyclohex-1-en-1-yl)ethanone；1-(2-phenyl-cyclohex-1-enyl)-ethanone；1-(2-Phenyl-cyclohex-1-enyl)-aethanon；1-(2-Phenylcyclohexen-1-yl)ethanone
• CAS: 72157-48-3
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: WXXWLISPZGGJIM-UHFFFAOYSA-N

物化性质

• 沸点：
  118 °C(Press: 1.5 Torr)
• 密度：
  1.047 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-Phenyl-1-acetylcyclohexene 在 乙醇 、 镍 作用下， 生成 (+/-)-1-(cis-2-phenyl-cyclohexyl)-ethanone
  参考文献：
  名称：

  Colonge; Bonnard, Bulletin de la Societe Chimique de France, 1958, p. 1491,1494

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰基环己酮 在 四(三苯基膦)钯 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 48.0h， 生成 2-Phenyl-1-acetylcyclohexene
  参考文献：
  名称：

  Palladium-catalyzed cross-coupling of .beta.-(methanesulfonyl)oxyenones with organostannanes

  摘要：

  beta-(Methanesulfonyl)oxy enones, derived from 1,3-diones, cross-couple with vinylstannanes in 50-80% yields when a substoichiometric amount of Pd(PPh3)4 and stoichiometric lithium bromide are used. Phenyltributylstannane affords low yields of cross-coupled product. Tetrabutyltin, tributyltin hydride, and ethynyltributyltin do not couple under the reaction conditions. The reaction is proposed to involve in situ formation of the beta-bromo enone, oxidative addition to the Pd(0) catalyst, transmetalation, and reductive elimination to afford cross-coupled products. The analogous enol phosphates undergo coupling in low yields, the major product resulting from regeneration of the 1,3-dione.

  DOI：

  10.1021/jo00004a028

文献信息

• NITROGEN-CONTAINING SATURATED HETEROCYCLIC COMPOUND
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20160221948A1

  公开（公告）日：2016-08-04

  The present invention provides a compound represented by the following formula (I) or its pharmaceutically acceptable salt: [wherein, R 1 represents optionally substituted C 1-4 alkyl, n shows integer of 1 to 4, R 2 represents optionally substituted C 1-4 alkyl or hydrogen atom, R 3 represents optionally substituted C 1-4 alkyl, R 4a , R 4b , R 4c , and R 4d , similarly or differently, represent optionally substituted C 6-14 aryl, optionally substituted C 1-4 alkyl, or hydrogen atom and the like, A represents optionally substituted C 6-14 aryl or optionally substituted 5 to 11 membered heteroaryl].

  本发明提供了一种由下式(I)表示的化合物或其药用可接受的盐： [其中，R1表示可选地取代的C1-4烷基，n表示1到4的整数，R2表示可选地取代的C1-4烷基或氢原子，R3表示可选地取代的C1-4烷基，R4a、R4b、R4c和R4d，相同或不同，表示可选地取代的C6-14芳基，可选地取代的C1-4烷基，或氢原子等，A表示可选地取代的C6-14芳基或可选地取代的5至11成员的杂芳基]。
• Iridium-Catalyzed Asymmetric Hydrogenation of α-Substituted α,β-Unsaturated Acyclic Ketones: Enantioselective Total Synthesis of (−)-Mesembrine
  作者：Qian-Qian Zhang、Jian-Hua Xie、Xiao-Hui Yang、Jian-Bo Xie、Qi-Lin Zhou

  DOI：10.1021/ol302842h

  日期：2012.12.21

  A highly efficient asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones catalyzed by chiral spiro iridium complexes for the preparation of chiral 2-substituted allylic alcohols has been developed (ee up to 99.7%). This method provides a concise route to (−)-mesembrine (34% yield, 12 steps).

  已经开发了由手性螺铱配合物催化的α-取代的α，β-不饱和无环酮的高效不对称氢化，用于制备手性2-取代的烯丙基醇（ee高达99.7％）。该方法提供了通往（-）-中间膜的简洁途径（34％的产率，12个步骤）。
• Iron-Catalyzed Stereospecific Activation of Olefinic C–H Bonds with Grignard Reagent for Synthesis of Substituted Olefins
  作者：Laurean Ilies、Sobi Asako、Eiichi Nakamura

  DOI：10.1021/ja2017202

  日期：2011.5.25

  The reaction of an aryl Grignard reagent with a cyclic or acyclic olefin possessing a directing group such as pyridine or imine results in the stereospecific substitution of the olefinic C-H bond syn to the directing group. The reaction takes place smoothly and without isomerization of the product olefin in the presence of a mild oxidant (1,2-dichloro-2-methylpropane) and an aromatic cosolvent. Several

  芳基格氏试剂与具有导向基团（例如吡啶或亚胺）的环状或无环烯烃的反应导致烯属 CH 键顺式立体定向取代为导向基团。在温和氧化剂（1,2-二氯-2-甲基丙烷）和芳香族助溶剂的存在下，反应平稳进行且产物烯烃没有异构化。几条证据表明，该反应是通过铁催化的烯烃 CH 键活化而不是氧化性 Mizoroki-Heck 型反应进行的。
• Allen; Rudoff, Canadian Journal of Research, Section B: Chemical Sciences, 1937, vol. 15, p. 321,329
  作者：Allen、Rudoff

  DOI：——

  日期：——
• Stanley,K.L.M. et al., Journal of the Chemical Society. Perkin transactions I, 1979, p. 1433 - 1441
  作者：Stanley,K.L.M. et al.

  DOI：——

  日期：——