methyl 2,2-dichloro-2-(methoxycarbonylmethylthio)acetate | 176848-01-4

• 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: methyl 2,2-dichloro-2-(methoxycarbonylmethylthio)acetate
• 英文别名: Methyl 2,2-dichloro-2-(2-methoxy-2-oxoethyl)sulfanylacetate
• CAS: 176848-01-4
• 化学式: C₆H₈Cl₂O₄S
• 分子量: 247.099
• InChiKey: ARHUWFHNMJUMLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,2-dichloro-2-(methoxycarbonylmethylthio)acetate 在 triethylamine tris(hydrogen fluoride) 、 zinc dibromide 作用下， 以 乙腈 为溶剂， 反应 5.5h， 以75%的产率得到Difluoro-methoxycarbonylmethylsulfanyl-acetic acid methyl ester
  参考文献：
  名称：

  Fluorination of α,α-dichlorosulfides: access to gem-difluorothioethers as useful building blocks

  摘要：

  The synthesis of alkylsulfanyidifluoro-acetate and ketones by the Halex reaction is described. The remarkable reactivity of thiodifluoroacetate derivatives opened rapid access for the preparation of useful building blocks such as gem-difluoroketones and amides. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01134-1
• 作为产物：
  描述：

  硫代二乙酸二甲酯 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2,2-dichloro-2-(methoxycarbonylmethylthio)acetate
  参考文献：
  名称：

  First Synthesis of 4,4-Difluoro-1,3-oxathiolan-5-one

  摘要：

  据报道，一种新型 4,4-二氟-1,3-氧硫杂环戊酮是由δ,δ±-二氟亚砜合成的。这条路线涉及对称硫化物的氟化、普默尔重排和有机酸介导的闭环。

  DOI：

  10.1055/s-2002-31912

文献信息

• Synthesis of α-fluorinated-α,α-difunctionalized sulfides and sulfones
  作者：C. Jouen、M.C. Lasne、J.C. Pommelet

  DOI：10.1016/0040-4039(96)00186-4

  日期：1996.4

  The highly functionalized organofluorine compounds 3a-c were prepared from the activated dichlorinated sulfides 2a-c by displacement of a chlorine atom using nucleophilic fluorination agents such as dihydrogenfluoride polymer-supported. Fluorination of sulfoxides 5a-c with diethylaminosulfur trifluoride gives monofluoro sulfides 6a-c, subsequently transformed into α-chloro-α-fluoro sulfides 3a-c and

  通过使用亲核氟化剂（例如，聚合物支撑的氟化二氢）通过置换氯原子，由活化的二氯化硫化物2a-c制备高度官能化的有机氟化合物3a-c。用三氟化二乙基氨基硫将亚砜5a-c氟化，得到一氟硫化物6a-c，随后转化为α-氯-α-氟硫化物3a-c和砜7a-c。
• Monofluorination of α-dichlorosulfides: A short access to α-fluoro polyfunctionalised thioethers
  作者：C Jouen、J.C Pommelet

  DOI：10.1016/s0040-4020(97)00778-3

  日期：1997.9

  alpha-Chlorinated-alpha-fluorinated thioethers were synthesized in good yields by nucleophilic fluorination of their corresponding dichlorinated thioethers. A complete conversion of dihalosulfides 2 into alpha-fluoro-alpha-chlorosulfides 3 was achieved with Et3N.3HF in refluxing acetonitrile. (C) 1997 Elsevier Science Ltd.
• Fluorination of α,α-dichlorosulfides: access to gem-difluorothioethers as useful building blocks
  作者：Sonia Gouault、Cécile Guérin、Laurent Lemoucheux、Thierry Lequeux、Jean-Claude Pommelet

  DOI：10.1016/s0040-4039(03)01134-1

  日期：2003.6

  The synthesis of alkylsulfanyidifluoro-acetate and ketones by the Halex reaction is described. The remarkable reactivity of thiodifluoroacetate derivatives opened rapid access for the preparation of useful building blocks such as gem-difluoroketones and amides. (C) 2003 Elsevier Science Ltd. All rights reserved.
• First Synthesis of 4,4-Difluoro-1,3-oxathiolan-5-one
  作者：Sonia Gouault、Jean-Claude Pommelet、Thierry Lequeux

  DOI：10.1055/s-2002-31912

  日期：——

  The synthesis of a novel 4,4-difluoro-1,3-oxathiolanone was reported from α,α-difluorosulfoxide. This route involved a fluorination of a symmetrical sulfide, a Pummerer rearrangement, and a ring closure mediated by organic acids.

  据报道，一种新型 4,4-二氟-1,3-氧硫杂环戊酮是由δ,δ±-二氟亚砜合成的。这条路线涉及对称硫化物的氟化、普默尔重排和有机酸介导的闭环。