(3-(4-chlorophenyl)oxiran-2-yl)(p-tolyl)methanone | 27547-09-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-(4-chlorophenyl)oxiran-2-yl)(p-tolyl)methanone
• 英文别名: p-tolyl-3-(4-chlorophenyl)oxiran-2-yl-methanone；p-tolyl-3-(4-chlorophenyl)oxiran-2-ylmethanone；[3-(4-chloro-phenyl)-oxiranyl]-p-tolyl-methanone；[3-(4-Chlorophenyl)oxiran-2-yl]-(4-methylphenyl)methanone
• CAS: 27547-09-7；32157-67-8
• 化学式: C₁₆H₁₃ClO₂
• 分子量: 272.731
• InChiKey: GTTWIOBAHIEOMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  103-106 °C(Solv: hexane (110-54-3); acetone (67-64-1))
• 沸点：
  419.2±45.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-(4-chlorophenyl)oxiran-2-yl)(p-tolyl)methanone 在 三光气 、 N,N-二甲基甲酰胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以55%的产率得到(Z)-2-chloro-3-(4-chlorophenyl)-1-(p-tolyl)prop-2-en-1-one
  参考文献：
  名称：

  An approach to synthesis of (Z)-2-chloro-1,3-diarylpropen-1-ones by Vilsmeier reagent (bis-(trichloromethyl) carbonate/DMF)

  摘要：

  A series of (Z)-2-chloro-1,3-diarylpropen-1-ones were unexpectedly synthesized in moderate yields by treatment of easily available 2,3-epoxy-1, 3-diarylpropan-1-ones with Vilsmeier reagent, which was derived from bis(trichloromethyl) carbonate (BTC, triphosgene) and DMF. A possible mechanism was also proposed, where sequential ring-opening, halogenation and elimination reactions were involved. (C) 2011 Wei Ke Su. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.07.006
• 作为产物：
  描述：

  (E)-4-chloro-4'-methylchalcone 在 urea-2,2-dihydroperoxypropane 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.3h， 以97%的产率得到(3-(4-chlorophenyl)oxiran-2-yl)(p-tolyl)methanone
  参考文献：
  名称：

  尿素-2,2-二氢过氧丙烷作为新型氧化剂，可轻松进行α，β-不饱和酮的环氧化

  摘要：

  摘要首次使用脲-2,2-二氢过氧丙烷作为氧源，成功地将各种芳香族α，β-不饱和酮转化为相应的环氧化物。反应在室温下在弱碱性条件下以高产率和短反应时间进行。 图形概要

  DOI：

  10.1007/s13738-016-0980-1

文献信息

• Metal-Free and Efficient Epoxidation of α,β-Unsaturated Ketones with 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as a Powerful Solid Oxidant
  作者：Kaveh Khosravi、Shirin Naserifar、Boshra Mahmoudi

  DOI：10.1002/jccs.201700026

  日期：2017.6

  1,1,2,2‐Tetrahydroperoxy‐1,2‐diphenylethane was used for the efficient and metal‐free epoxidation of various α,β‐unsaturated ketones, carried out under mild alkaline conditions at room temperature.

  1,1,2,2-四氢过氧1,2-二苯乙烷用于各种α，β-不饱和酮的高效无金属环氧化，在室温下于弱碱性条件下进行。
• <font>β</font>-Cyclodextrin in Water: Highly Versatile and Green Approach for Biomimetic Regioselective Ring Opening of Chalcone Epoxides with Nitrogen Heterocycles
  作者：Sumit Kumar、Naveen Kumar Konduru、Nishant Verma、Naseem Ahmed

  DOI：10.1080/00397911.2015.1093142

  日期：2015.11.17

  The formation of new C-C bond through highly regioselective ring opening of chalcone epoxides to nitrogen-containing heterocycles has been effectively worked out in impressive yields with heterocyclic nucleophiles such as pyrrole, indole, and 2-methyl indole in the presence of β-cyclodextrin using water as solvent at room temperature within 25–50 min. Water, an environmentally friendly reaction medium

  摘要 使用杂环亲核试剂如吡咯、吲哚和 2-甲基吲哚，在 β-环糊精存在下，通过查耳酮环氧化物高度区域选择性开环形成含氮杂环，形成新的 CC 键已得到有效解决，产率令人印象深刻。水作为溶剂在室温下在 25-50 分钟内。水是一种环境友好的反应介质，首次用于这些杂环亲核试剂与查耳酮环氧化物作为其 β-环糊精配合物的反应，得到 1,3-二芳基-2-羟基-3-(1H-3-吲哚基/2-吡咯基）丙-1-酮（3a-u）。催化剂可以很容易地回收和循环使用多次而不会损失活性。图形概要
• A transition-metal-free, one-pot procedure for the synthesis of α,β-epoxy ketones by oxidative coupling of alkenes and aldehydes via base catalysis
  作者：Qingping Ke、Bingyan Zhang、Bolun Hu、Yangxin Jin、Guanzhong Lu

  DOI：10.1039/c4cc09260k

  日期：——

  A new strategy for the synthesis of epoxides is presented.

  一种合成环氧化物的新策略被提出。
• LiBr/β-CD/IBX/H₂O-DMSO: A new approach for one-pot biomimetic regioselective ring opening of chalcone epoxides to bromohydrins and conversion to 1,2,3-triketones
  作者：Nishant Verma、Sumit Kumar、Naseem Ahmed

  DOI：10.1080/00397911.2017.1315537

  日期：2017.6.3

  ABSTRACT Highly regioselective ring cleavage of chalcone epoxides to bromohydrins has been carried out in good yields with LiBr in the presence of β-CD using DMSO-H2O as solvent system. The ring-opened product, i.e., bromohydrin, was well adapted to IBX-mediated oxidation in such a fashion that the bromohydrins are transformed to their corresponding 1,2,3-triketones in moderate-to-good yields in one

  摘要 在 β-CD 存在下，使用 DMSO-H2O 作为溶剂系统，使用溴化锂以良好的收率将查尔酮环氧化物的高区域选择性环裂解成溴醇。开环产物，即溴代醇，以这样一种方式很好地适应了 IBX 介导的氧化，使得溴代醇在一锅中以中等至良好的产率转化为其相应的 1,2,3-三酮。图形概要
• One-pot synthesis of chalcone epoxides—A green chemistry strategy
  作者：Dalyna Ngo、Mbelu Kalala、Victoria Hogan、Renuka Manchanayakage

  DOI：10.1016/j.tetlet.2014.06.057

  日期：2014.8

  Waste minimization is a very important aspect of an environmentally benign protocol. A one-pot consec-process has been developed for chalcone epoxide synthesis that allows compounds to be prepared having to isolate and purify the intermediates. The strategy utilizes consecutive Claisen Schmidt and epoxidation reactions to prepare chalcone epoxides from substituted benzaldehydes acetophenones in good yields. (C) 2014 Elsevier Ltd. All rights reserved.