(4-chlorophenyl)-3-(3-nitrophenyl)oxiran-2-yl-methanone | 874193-94-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-chlorophenyl)-3-(3-nitrophenyl)oxiran-2-yl-methanone
• 英文别名: (4-chlorophenyl)-[3-(3-nitrophenyl)oxiran-2-yl]methanone
• CAS: 874193-94-9
• 化学式: C₁₅H₁₀ClNO₄
• 分子量: 303.702
• InChiKey: FZECDMVSTGREBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  72.74
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4-chlorophenyl)-3-(3-nitrophenyl)oxiran-2-yl-methanone 在 β-环糊精 、 lithium bromide 、 2-碘酰基苯甲酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 9.5h， 以78%的产率得到1-(4-chlorophenyl)-3-(3-nitrophenyl)propane-1,2,3-trione
  参考文献：
  名称：

  LiBr/β-CD/IBX/H2O-DMSO：一种单锅仿生区域选择性开环查尔酮环氧化物为溴醇并转化为 1,2,3-三酮的新方法

  摘要：

  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

  DOI：

  10.1080/00397911.2017.1315537
• 作为产物：
  描述：

  1-(4-chlorophenyl)-3-(3-nitrophenyl)prop-2-en-1-one 在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以87%的产率得到(4-chlorophenyl)-3-(3-nitrophenyl)oxiran-2-yl-methanone
  参考文献：
  名称：

  Regioselective Opening of Chalcone Epoxides with Nitrogen Heterocycles Using Indium(III) Chloride as an Efficient Catalyst

  摘要：

  Indium(III) chloride catalyzes regioselective ring opening of chalcone epoxides with nitrogen heterocycles such as indole, 2-methyl indole, and pyrrole under mild conditions at room temperature to afford 1,3-diaryl-2-hydroxy-3-(1H-3-indolyl/2-pyrrolyl)propan-1-ones in good yields (6088%) within 2050min. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.667291

文献信息

• <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
• An approach to synthesis of (Z)-2-chloro-1,3-diarylpropen-1-ones by Vilsmeier reagent (bis-(trichloromethyl) carbonate/DMF)
  作者：Yi Yi Weng、Jian Jun Li、Wei Ke Su

  DOI：10.1016/j.cclet.2011.07.006

  日期：2011.12

  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.
• 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
• Regioselective Opening of Chalcone Epoxides with Nitrogen Heterocycles Using Indium(III) Chloride as an Efficient Catalyst
  作者：Naveen Kumar Konduru、Naseem Ahmed

  DOI：10.1080/00397911.2012.667291

  日期：2013.8.3

  Indium(III) chloride catalyzes regioselective ring opening of chalcone epoxides with nitrogen heterocycles such as indole, 2-methyl indole, and pyrrole under mild conditions at room temperature to afford 1,3-diaryl-2-hydroxy-3-(1H-3-indolyl/2-pyrrolyl)propan-1-ones in good yields (6088%) within 2050min. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.