α,α-dichlorophenylacetaldehyde | 50735-77-8

• 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: α,α-dichlorophenylacetaldehyde
• 英文别名: 2,2-Dichlor-2-phenylacetaldehyd；(dichlorophenyl)acetaldehyde；2,2-dichloro-2-phenylethanal；2,2-dichloro-2-phenylacetaldehyde；Dichloro(phenyl)acetaldehyde
• CAS: 50735-77-8
• 化学式: C₈H₆Cl₂O
• 分子量: 189.041
• InChiKey: NXZHTMYGZGIPNT-UHFFFAOYSA-N

物化性质

• 沸点：
  107-109 °C(Press: 12 Torr)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  α,α-dichlorophenylacetaldehyde 在 磷酸 、 sodium methylate 作用下， 生成 苯基丙醇水合物
  参考文献：
  名称：

  Preparation of 1,1-Dialkoxy-2-alkanones

  摘要：

  DOI：

  10.1055/s-1982-29895
• 作为产物：
  描述：

  L-苯丙氨酸 生成 α,α-dichlorophenylacetaldehyde
  参考文献：
  名称：

  HORTH, H., AQUA, 38,(1989) N, C. 80-100

  摘要：

  DOI：

文献信息

• Use of Phenylselenium Trichloride For Simple and Rapid Preparation of α-Phenylselanyl Aldehydes and Ketones
  作者：Didier Houllemare、Sylvain Ponthieux、Francis Outurquin、Claude Paulmier

  DOI：10.1055/s-1997-1509

  日期：1997.1

  α-Phenylselanyl aldehydes are prepared on a large scale by reaction of PhSeCl3 with the corresponding aldehydes in acetonitrile without isolation of the intermediate dichloro adducts. This method has been applied to α-phenylselanyl ketones derived from alkyl aryl ketones, symmetrical aliphatic ketones and alkyl isopropyl ketones. cis-4-tert-Butyl-2-phenylselanylcyclohexanone was also prepared in the same way.

  α-苯硒基醛通过PhSeCl3与相应醛在乙腈中反应大规模制备，无需分离二氯加成中间体。该方法已应用于由烷基芳基酮、对称脂肪酮和烷基异丙基酮衍生的α-苯硒基酮，并同样制备了顺-4-叔丁基-2-苯硒基环己酮。
• Synthesis of <i>trans</i>-2-Substituted Cyclopropylamines from α-Chloroaldehydes
  作者：Michael S. West、L. Reginald Mills、Tyler R. McDonald、Jessica B. Lee、Deeba Ensan、Sophie A. L. Rousseaux

  DOI：10.1021/acs.orglett.9b03172

  日期：2019.10.18

  report the synthesis of trans-2-substituted cyclopropylamines in high diastereoselectivity from readily available α-chloroaldehydes. The reaction proceeds via trapping of an electrophilic zinc homoenolate with an amine followed by ring closure to generate the cyclopropylamine. We have also observed that cyclopropylamine cis/trans-isomerization occurs in the presence of zinc halide salts and that this

  环丙胺在药物和农用化学品中普遍存在。在本文中，我们报道了从容易获得的α-氯醛以高非对映选择性合成反式-2-取代的环丙胺。该反应通过用胺捕获亲电性均烯酸锌来进行，然后闭环以产生环丙胺。我们还观察到环丙胺的顺/反异构化在卤化锌盐的存在下发生，并且可以通过添加极性非质子助溶剂来关闭该过程。
• Synthesis of 3-arylcoumarins through N-heterocyclic carbene catalyzed condensation and annulation of 2-chloro-2-arylacetaldehydes with salicylaldehydes
  作者：Yuansong Jiang、Wanzhi Chen、Weimin Lu

  DOI：10.1016/j.tet.2013.03.025

  日期：2013.5

  The condensation reaction of 2-chloro-2-arylacetaldehyde with salicylaldehyde catalyzed by N-heterocyclic carbene (NHC) leading to 3-arylcoumarin was studied. A number of 3-arylcoumarin derivatives were obtained in good to excellent yields via this umpolung reaction. This reaction is facile and experimentally simple and mild.

  研究了N-杂环卡宾（NHC）催化2-氯-2-芳基乙醛与水杨醛的缩合反应，生成3-芳基香豆素。通过这种化学反应，以良好的产率获得了许多3-芳基香豆素衍生物。该反应是容易的，并且实验上简单温和。
• RING CLEAVAGE OF EPOXIDES WITH THIOANISOLE–CHLORINE COMPLEX: A SIMPLE SYNTHESIS OF α-CHLOROCARBONYL COMPOUNDS
  作者：Hisao Nakai、Masayasu Kurono

  DOI：10.1246/cl.1977.995

  日期：1977.8.5

  The reaction of epoxides (1) with thioanisole-chlorine complex (2) produced α-chlorosulfoxonium intermediates (3a and/or 3b), which were quenched with aqNaHCO3 to afford α-chloroalcohols (4a and/or 4b). The intermediate (3a and/or 3b) gave α-chlorocarbonyl compounds (5a and/or 5b) by treatment with triethylamine.

  环氧化物 (1) 与苯甲硫醚-氯络合物 (2) 的反应产生 α-氯代锍中间体 (3a 和/或 3b)，用 aqNaHCO3 淬灭，得到 α-氯醇 (4a 和/或 4b)。通过用三乙胺处理，中间体(3a和/或3b)得到α-氯羰基化合物(5a和/或5b)。
• Preparation of acid chlorides
  申请人：OCCIDENTAL CHEMICAL CORPORATION, Occidental Tower

  公开号：EP0916641A1

  公开（公告）日：1999-05-19

  In a method of making an acid chloride having the general formula where each R contains no unsaturated groups and is preferably independently selected from aliphatic from C1 to C7 and aryl from C6 to C15, a solution is formed in an inert solvent of an aldehyde having the general formula and chlorine gas is sparged into said solution. The reaction between the aldehyde and the chlorine gas to produce the acid chloride is performed in the absence of a catalyst, in the absence of an initiator, and in the absence of ultraviolet light. A chlorinated acid chloride can be prepared from the acid chloride by reacting it with additional chlorine in the presence of a chlorine free radical generator.

  通式如下的氯化酸的制造方法 其中每个 R 不含不饱和基团，且最好独立地选自 C1 至 C7 脂肪族和 C6 至 C15 芳族，在惰性溶剂中形成通式如下的醛溶液 并向所述溶液中通入氯气。醛和氯气之间生成氯化酸的反应是在无催化剂、无引发剂和无紫外线的情况下进行的。在有氯自由基发生器存在的情况下，通过与额外的氯反应，可以从酰氯中制备出氯化酸。