3,3-dichloropropionic acid | 22716-03-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,3-dichloropropionic acid
• 英文别名: dichloroacetate；3,3-dichloro-propionic acid；3,3-Dichlor-propionsaeure；β.β-Dichlor-propionsaeure；3.3-Dichlor-propansaeure-(1)；3,3-dichloro-propanoic acid；3,3-dichloropropanoic acid
• CAS: 22716-03-6
• 化学式: C₃H₄Cl₂O₂
• mdl: MFCD00086352
• 分子量: 142.97
• InChiKey: HFPLCFMATPQWMD-UHFFFAOYSA-N

物化性质

• 熔点：
  54 °C(Solv: ligroine (8032-32-4))
• 沸点：
  76-78 °C(Press: 1.5 Torr)
• 密度：
  1.491±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3-dichloropropionic acid 在 氯化亚砜 作用下， 生成 dichloropropionyl chloride
  参考文献：
  名称：

  Leimu, Chemische Berichte, 1937, vol. 70, p. 1042

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,4-trichloro-but-1-ene 在 potassium permanganate 作用下， 生成 3,3-dichloropropionic acid
  参考文献：
  名称：

  有机氘化合物：十八。氢和溴化氘的加成产物到 1,1-二氯乙烯

  摘要：

  在紫外线照射下将溴化氢加入 1,1-二氯乙烯中，得到两种产物，分别为 1-溴-2,2-二氯乙烷和 1-溴-2,2,4,4-四氯丁烷。使用溴化氘，形成相应的氘代卤化物。1-Chloroethene-1-d 由 1-bromo-2,2-dichloroethane-2-d 制备。

  DOI：

  10.1139/v57-070

文献信息

• Visible Light-Induced Oxidative Chlorination of Alkyl sp³ C–H Bonds with NaCl/Oxone at Room Temperature
  作者：Mengdi Zhao、Wenjun Lu

  DOI：10.1021/acs.orglett.7b02153

  日期：2017.9.1

  light-induced monochlorination of cyclohexane with sodium chloride (5:1) has been successfully accomplished to afford chlorocyclohexane in excellent yield by using Oxone as the oxidant in H2O/CF3CH2OH at room temperature. Other secondary and primary alkyl sp3 C–H bonds of cycloalkanes and functional branch/linear alkanes can also be chlorinated, respectively, under similar conditions. The selection of

  通过在室温下在H 2 O / CF 3 CH 2 OH中使用Oxone作为氧化剂，已成功完成了可见光诱导的氯化钠（5：1）对环己烷的单氯化，以优异的产率提供了氯环己烷。环烷烃和功能性支链/直链烷烃的其他仲和仲烷基sp 3 C–H键也可以在类似条件下分别进行氯化。在两相溶液中烷烃的有效自由基氯化中，选择合适的有机溶剂至关重要。通过在甲苯的苄基sp 3 C–H键或芳基sp 2 C–H键氯化中实现高化学选择性，可以对它进行进一步的研究。
• Ketone-catalyzed photochemical C(sp3)–H chlorination
  作者：Lei Han、Ji-Bao Xia、Lin You、Chuo Chen

  DOI：10.1016/j.tet.2017.05.008

  日期：2017.6

  Photoexcited arylketones catalyze the direct chlorination of C(sp3)–H groups by N- chlorosuccinimide. Acetophenone is the most effective catalyst for functionalization of unactivated C–H groups while benzophenone provides better yields for benzylic C–H functionalization. Activation of both acetophenone and benzophenone can be achieved by irradiation with a household compact fluorescent lamp. This light-dependent

  光激发芳基酮通过N - 氯代琥珀酰亚胺催化 C(sp 3 )–H 基团的直接氯化。苯乙酮是未活化 C-H 基团官能化最有效的催化剂，而二苯甲酮为苄基 C-H 官能化提供了更好的收率。苯乙酮和二苯甲酮都可以通过家用紧凑型荧光灯的照射来激活。与通过自由基链增长机制进行的传统氯化方法相比，这种光依赖性反应提供了更好的反应控制。
• Otto, Justus Liebigs Annalen der Chemie, 1887, vol. 239, p. 279
  作者：Otto

  DOI：——

  日期：——
• Glutathione Transferase Zeta-Catalyzed Biotransformation of Dichloroacetic Acid and Other α-Haloacids
  作者：Zeen Tong、Philip G. Board、M. W. Anders

  DOI：10.1021/tx980144f

  日期：1998.11.1

  Dichloroacetic acid (DCA) is a common drinking-water contaminant, is hepatocarcinogenic in rats and mice, and is a therapeutic agent used clinically in the management of lactic acidosis. Recent studies show that glutathione transferase Zeta (GSTZ) catalyzes the oxygenation of DCA to glyoxylic acid [Tong et al. (1998) Biochem. J. 331, 371-374]. In the present studies, the substrate selectivity of GSTZ, the kinetics of DCA metabolism, and the fate of DCA and glutathione were investigated. The results showed that GSTZ catalyzed the oxygenation of bromochloro-, bromofluoro-, chlorofluoro-, dibromo-, and dichloroacetic acid, but not difluoroacetic acid, to glyoxylic acid. GSTZ also catalyzed the biotransformation of fluoroacetic acid to S-(carboxymethyl)glutathione, and of(R, S)-2-bromopropionic acid, (R)-, (S)-, and (R,S)-2-chloropropionic acid, and (R,S)-2-iodopropionic acid, but not (R,S)-2-fluoropropionic acid, to S-(alpha-methylcarboxymethyl)glutathione; and of 2,2-dichloropropionic acid to pyruvate. No biotransformation of 3,3-dichloropropionic acid was detected, and no GSTZ-catalyzed fluoride release from ethyl fluoroacetate and fluoroacetamide was observed. The relative rates of DCA biotransformation by hepatic cytosol were mouse > rat > human. Immunoblotting showed the presence of GSTZ in mouse, rat, and human liver cytosol. C-13 NMR spectroscopic studies showed that [2-C-13]glyoxylic acid was the only observable, stable metabolite of [2-13C]DCA. Also, glutathione was required, but was neither consumed nor oxidized to glutathione disulfide, during the oxygenation of DCA to glyoxylic acid. These results are consistent, with a reaction mechanism that involves displacement of chloride from DCA by glutathione to afford S-(alpha-chlorocarboxymethyl)glutathione, which may undergo hydrolysis to give the hemithioacetal S-(alpha-hydroxycarboxymethyl)glutathione. Elimination of glutathione from the hemithioacetal would give glyoxylic acid.
• Leimu, Chemische Berichte, 1937, vol. 70, p. 1042
  作者：Leimu

  DOI：——

  日期：——