3-chloro-1,3-diphenyl-1,2-propanedione | 97295-30-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-chloro-1,3-diphenyl-1,2-propanedione
• 英文别名: 3-chloro-1,3-diphenylpropane-1,2-dione
• CAS: 97295-30-2
• 化学式: C₁₅H₁₁ClO₂
• 分子量: 258.704
• InChiKey: XSACTKBVPBCDTA-UHFFFAOYSA-N

物化性质

• 沸点：
  376.2±35.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-1,3-diphenyl-1,2-propanedione 在 溶剂黄146 、 三乙胺 作用下， 反应 16.0h， 生成 2-phenyl-3-(α-methoxybenzyl)quinoxaline
  参考文献：
  名称：

  Medium effect on the direction of the reaction of 3-chloro-1,3-diphenyl-1,2-propanedione with ortho-phenylenediamine

  摘要：

  The reaction of 3-chloro-1,3-diphenyl-1,2-propanedione (I) with ortho-phenylenediamine in acetic acid gave 2-phenyl-3-(alpha-chlorobenzyl)quinoxaline (II). This reaction in methanol with MeONa gave 2-(alpha-hydroxybenzylidene)-3-phenyl-1,4-dihydroquinoxaline (VI).

  DOI：

  10.1007/bf00961256
• 作为产物：
  描述：

  4-morpholinylacetophenone 在 盐酸 、 sodium hydroxide 、 四丁基溴化铵 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 3-chloro-1,3-diphenyl-1,2-propanedione
  参考文献：
  名称：

  Reactions of organic anions. 122. Reactions of carbanions with carbon tetrachloride in two-phase systems. Chlorinated products as nucleophilic and electrophilic intermediates

  摘要：

  DOI：

  10.1021/jo00220a010

文献信息

• Highly Diastereo- and Enantioselective Organocatalytic Domino Michael/Aldol Reaction of Acyclic 3-Halogeno-1,2-Diones to α,β-Unsaturated Aldehydes
  作者：Alice Lefranc、Laure Guénée、Alexandre Alexakis

  DOI：10.1021/ol400697n

  日期：2013.5.3

  The first organocatalytic diastereo- and enantioselective domino Michael/aldol reaction of 3-halogeno-1,2-diones to α,β-unsaturated aldehydes has been achieved. This transformation tolerates a large variety of electronically different substituents on both reactive partners and allows the synthesis of challenging cyclopentanone derivatives with four contiguous stereogenic centers in excellent diastereoselectivities

  已经实现了3-卤代1,2-二酮与α，β-不饱和醛的第一有机催化非对映和对映选择性多米诺迈克尔/醛醇缩合反应。这种转化在两个反应伙伴上都可以耐受多种电子上不同的取代基，并可以合成具有四个非连续立体异构中心（> 20：1 dr）且产率高（69-97％）的具有挑战性的具有四个连续立体中心的环戊酮衍生物。对映选择性（高达94％ee）。
• Reaction of 2,2-dichloroacetophenone and benzaldehydes under conditions of the darzens condensation
  作者：V. A. Mamedov、V. L. Polushina、F. F. Mertsalova、I. A. Nuretdinov

  DOI：10.1007/bf00863938

  日期：1992.1

  The reaction of 2,2-dichloroacetophenone with benzaldehydes was studied under Darzens condensation conditions. Benzaldehyde, p-bromobenzaldehyde, and o,p-dichlorobenzaldehyde condensed with 2,2-dichloroacetophenone to give 1-phenyl-3-aryl-3-chloro-1,2-propanediones. In the case of p-nitrobenzaldehyde, 1-phenyl-2-chloro-3-(p-nitrophenyl)-2,3-epoxy-1-propanone, which is the product of the first step of the Darzens condensation, was isolated.
• Darzens reaction as a convenient method for the synthesis of ?-chloroketones, ?-chloroepoxides, and symmetrically substituted dioxines
  作者：V. A. Mamedov、I. A. Litvinov、O. N. Kataeva、I. Kh. Rizvanov、I. A. Nuretdinov

  DOI：10.1007/bf00811092

  日期：1994.12

  The Darzens reaction of dichloroacetophenone (DCAP) with substituted benzaldehydes has been studied. The structure of the products was shown to depend on the phenyl group substituents. Reaction of benzaldehyde, 4-bromo-, and 2,4-dichlorobenzaldehydes results in 1-phenyl-3-aryl-3-chloropropane-1,2-diones (2a-c), reaction of para- or meta-nitrobenzaldehydes yields 1-phenyl-2-chloro-3-aryl-2,3-epoxypropane-1-ones (3a, b). Upon the introduction of an alkoxy group into the phenyl ring of benzaldexyde and/or dichloroacetophenone, symmetrically substituted dioxines were obtained (6a-c). The structure of the reaction products has been established by single crystal X-ray investigations.
• MAMEDOV, V. A.;POLUSHINA, V. L.;MERTSALOVA, F. F.;NURETDINOV, I. A.;PLYAM+, IZV. AN CCCP. CEP. XIM.,(1991) N, S. 1660-1662
  作者：MAMEDOV, V. A.、POLUSHINA, V. L.、MERTSALOVA, F. F.、NURETDINOV, I. A.、PLYAM+

  DOI：——

  日期：——
• Mamedov V. A., Litvinov I. A., Kataeva O. N., Rizvanov I. Kh., Nuretdinov+, Monatsh. Chem, 125 (1994) N 12, S 1427-1435
  作者：Mamedov V. A., Litvinov I. A., Kataeva O. N., Rizvanov I. Kh., Nuretdinov+

  DOI：——

  日期：——