Ethyl 2-bromo-2-[difluoro(methylsulfonyl)methyl]-6-(2,2-dimethylpropanoyloxy)hexanoate | 816447-76-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl 2-bromo-2-[difluoro(methylsulfonyl)methyl]-6-(2,2-dimethylpropanoyloxy)hexanoate
• CAS: 816447-76-4
• 化学式: C₁₅H₂₅BrF₂O₆S
• 分子量: 451.327
• InChiKey: XJQGVZLIKWSPPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  95.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Ethyl 2-bromo-2-[difluoro(methylsulfonyl)methyl]-6-(2,2-dimethylpropanoyloxy)hexanoate 在 镍 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 ethyl 2-(4-pivaloyloxybutyl)-β,β-difluoroacrylate
  参考文献：
  名称：

  General Method for the Preparation of β,β-Difluoroacrylates Using BrF₃

  摘要：

  Various esters were reacted with base, carbon disulfide, and methyl iodide, producing 2-carboalkoxy1,1-bis(methyl sulfide)-1-alkenes (2). The reaction of 2 with BrF3, followed by oxidation with HOF-CH3CN gave the bromodifluorosulfonyl derivatives 5. Subsequent treatment with Raney nickel led to alpha-substituted beta,beta-difluoroacrylates 6 in overall yields of 50-80%.

  DOI：

  10.1021/jo0485280
• 作为产物：
  描述：

  Ethyl 2-[bis(methylsulfanyl)methylidene]-6-(2,2-dimethylpropanoyloxy)hexanoate 在 三氟化溴 、 air 、 sodium sulfite 、 HOF* CH₃CN 作用下， 以 一氟三氯甲烷 、 氯仿 为溶剂， 反应 0.33h， 生成 Ethyl 2-bromo-2-[difluoro(methylsulfonyl)methyl]-6-(2,2-dimethylpropanoyloxy)hexanoate
  参考文献：
  名称：

  General Method for the Preparation of β,β-Difluoroacrylates Using BrF₃

  摘要：

  Various esters were reacted with base, carbon disulfide, and methyl iodide, producing 2-carboalkoxy1,1-bis(methyl sulfide)-1-alkenes (2). The reaction of 2 with BrF3, followed by oxidation with HOF-CH3CN gave the bromodifluorosulfonyl derivatives 5. Subsequent treatment with Raney nickel led to alpha-substituted beta,beta-difluoroacrylates 6 in overall yields of 50-80%.

  DOI：

  10.1021/jo0485280

文献信息

• The first general method for α-trifluoromethylation of carboxylic acids using BrF₃
  作者：Aviv Hagooly、Shlomo Rozen

  DOI：10.1039/b315705a

  日期：——

  2-Carbomethoxy-1,1-bis(methylsulfide)-1-alkenes, easily made from carboxylic acids, CS2 and MeI, were treated with BrF3 producing eventually the desired α-trifluoromethyl carboxylate derivatives – RCH(CF3)COOR′ – in good yields.

  2-Carbomethoxy-1,1-bis(methylsulfide)-1-alkenes 很容易由羧酸、CS2 和 MeI 制成，用 BrF3 处理后，最终会以良好的收率生成所需的δ-三氟甲基羧酸衍生物 RCH(CF3)COORâ² 。
• General Method for the Preparation of β,β-Difluoroacrylates Using BrF₃
  作者：Aviv Hagooly、Shlomo Rozen

  DOI：10.1021/jo0485280

  日期：2004.12.1

  Various esters were reacted with base, carbon disulfide, and methyl iodide, producing 2-carboalkoxy1,1-bis(methyl sulfide)-1-alkenes (2). The reaction of 2 with BrF3, followed by oxidation with HOF-CH3CN gave the bromodifluorosulfonyl derivatives 5. Subsequent treatment with Raney nickel led to alpha-substituted beta,beta-difluoroacrylates 6 in overall yields of 50-80%.