2-(2-methylphenyl)cyclohexanone | 63882-42-8

• 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: 2-(2-methylphenyl)cyclohexanone
• 英文别名: (2S)-2-(2-methylphenyl)cyclohexan-1-one
• CAS: 63882-42-8
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: GIAVYZPYLHJCHT-LBPRGKRZSA-N

物化性质

• 熔点：
  55.5-56.5 °C(Solv: ligroine (8032-32-4))
• 沸点：
  115-130 °C(Press: 1 Torr)
• 密度：
  1.026±0.06 g/cm3(Predicted)

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：
  0.46
• 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：

  1-环己烯氧基三甲基硅烷 在 吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 2,6-二叔丁基苯酚 、 2,4-二硝基苯磺酸二水合物 、 (R)-N-(5,5,4,4,3,3,2,2-octafluoropentyl)-tert-butanesulfinamide 、 三正丁基氟化锡 、 sodium sulfate 、 三乙胺 、 sodium iodide 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 正己烷 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 44.0h， 生成 2-(2-methylphenyl)cyclohexanone 、 2-(2-methylphenyl)cyclohexanone
  参考文献：
  名称：

  Chiral Sulfinamide/Achiral Sulfonic Acid Cocatalyzed Enantioselective Protonation of Enol Silanes

  摘要：

  The application of chiral sulfinamides and achiral sulfonic acids as a cocatalyst system for enantioselective protonation reactions is described. Structurally simple, easily accessible sulfinamides were found to Induce moderate-to-high ee's in the formation of 2-aryl-substituted cycloalkanones from the corresponding trimethylsilyl enol ethers.

  DOI：

  10.1021/ol201608a

文献信息

• Arene CHO Hydrogen Bonding: A Stereocontrolling Tool in Palladium-Catalyzed Arylation and Vinylation of Ketones
  作者：Zhiyan Huang、Li Hui Lim、Zuliang Chen、Yongxin Li、Feng Zhou、Haibin Su、Jianrong Steve Zhou

  DOI：10.1002/anie.201300621

  日期：2013.4.26

  Weak is powerful: For the arylation of tin enolates, the palladium catalyst engages in weak CHO hydrogen bonds to control stereoselectivity (see scheme). Similar catalysts capable of NHO hydrogen bonding also works well.

  弱是有力：对于锡烯醇化物的芳基化，在弱CH钯催化剂接合 O氢键键合到控制立体选择性（参见方案）。能够进行NHO氢键键合的类似催化剂也能很好地工作。
• Enantioselective Protonation of Silyl Enol Ethers Catalyzed by a Chiral Pentacarboxycyclopentadiene-Based Brønsted Acid
  作者：Jun Li、Shaoyu An、Chao Yuan、Pingfan Li

  DOI：10.1055/s-0037-1611849

  日期：2019.7

  The enantioselective protonation of silyl enol ethers was realized in the presence of a pentacarboxycyclopenta-1,3-diene-based chiral Bronsted acid catalyst with water as an achiral proton source to give the corresponding α-aryl ketones in good yields and up to 75% ee.

  在基于五羧基环戊-1,3-二烯的手性布朗斯台德酸催化剂存在下，以水为非手性质子源实现甲硅烷基烯醇醚的对映选择性质子化，以良好的收率和高达 75% 的产率得到相应的 α-芳基酮ee。
• [EN] PALLADIUM-CATALYZED ASYMMETRIC (HETERO)ARYLATION AND VINYLATION OF KETONE ENOLATES TO PRODUCE TERTIARY STEREOCENTERS AT ALPHA(α)-POSITION<br/>[FR] (HÉTÉRO)ARYLATION ET VINYLATION ASYMÉTRIQUES D'ÉNOLATES DE CÉTONES CATALYSÉES AU PALLADIUM PERMETTANT DE PRODUIRE DES STÉRÉOCENTRES TERTIAIRES EN POSITION ALPHA(&Agr;)
  申请人：NANAYNG TECHNOLOGICAL UNIVERSITY

  公开号：WO2014109712A1

  公开（公告）日：2014-07-17

  The invention relates to new ligands that are used in a palladium source catalyst system and in palladium catalyzed method for asymmetric α-(hetero)arylation and a-vinylation of ketones. The invention further relates to a process for preparing an asymmetric α-(hetero)arylated or a-vinylated ketone which comprises reacting the tin enolate of the ketone in the presence of catalyst system comprising a ligand of the invention and palladium source. By means of the ligands and process of the invention a stereogenic center in position a of the ketone is established with high enantiomeric excess.
• Chiral Sulfinamide/Achiral Sulfonic Acid Cocatalyzed Enantioselective Protonation of Enol Silanes
  作者：Elizabeth M. Beck、Alan M. Hyde、Eric N. Jacobsen

  DOI：10.1021/ol201608a

  日期：2011.8.19

  The application of chiral sulfinamides and achiral sulfonic acids as a cocatalyst system for enantioselective protonation reactions is described. Structurally simple, easily accessible sulfinamides were found to Induce moderate-to-high ee's in the formation of 2-aryl-substituted cycloalkanones from the corresponding trimethylsilyl enol ethers.