Ethyl 1-methylsulfanylcarbothioylcycloheptane-1-carboxylate | 790691-89-3

• 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: Ethyl 1-methylsulfanylcarbothioylcycloheptane-1-carboxylate
• CAS: 790691-89-3
• 化学式: C₁₂H₂₀O₂S₂
• 分子量: 260.422
• InChiKey: MICYXGWAJXEXCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  83.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 1-methylsulfanylcarbothioylcycloheptane-1-carboxylate 在 盐酸 、 三氟化溴 、 乙醇 、 氢氟酸 作用下， 以 一氟三氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 Ethyl 1-(trifluoromethyl)cycloheptane-1-carboxylate
  参考文献：
  名称：

  α-Trifluoromethylation of Secondary and Sterically Hindered Carboxylates with Use of BrF₃

  摘要：

  Secondary esters and those with sterical hindrance at the beta carbon were reacted with base, carbon disulfide, and methyl iodide to produce methyl 2-carboalkoxydithioalkenoate (2). These compounds were reacted with BrF3, forming the corresponding alpha-trifluoromethyl esters (3) along with 1,1-difluoro-2-trifluoromethyl-2-alkyl ethers (4). The products of type 4 have been transformed to derivatives of type 3, thus raising the overall yields of the target respective cc-trifluoromethyl esters to 65-80%. The reaction is tolerant to different functional groups such as halogens, protected alcohols, esters, and lactones.

  DOI：

  10.1021/jo048864g
• 作为产物：
  描述：

  二硫化碳 、 乙基环庚烷羧酸酯 、 碘甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 3.0h， 以90%的产率得到Ethyl 1-methylsulfanylcarbothioylcycloheptane-1-carboxylate
  参考文献：
  名称：

  α-Trifluoromethylation of Secondary and Sterically Hindered Carboxylates with Use of BrF₃

  摘要：

  Secondary esters and those with sterical hindrance at the beta carbon were reacted with base, carbon disulfide, and methyl iodide to produce methyl 2-carboalkoxydithioalkenoate (2). These compounds were reacted with BrF3, forming the corresponding alpha-trifluoromethyl esters (3) along with 1,1-difluoro-2-trifluoromethyl-2-alkyl ethers (4). The products of type 4 have been transformed to derivatives of type 3, thus raising the overall yields of the target respective cc-trifluoromethyl esters to 65-80%. The reaction is tolerant to different functional groups such as halogens, protected alcohols, esters, and lactones.

  DOI：

  10.1021/jo048864g

文献信息

• α-Trifluoromethylation of Secondary and Sterically Hindered Carboxylates with Use of BrF₃
  作者：Aviv Hagooly、Shlomo Rozen

  DOI：10.1021/jo048864g

  日期：2004.10.1

  Secondary esters and those with sterical hindrance at the beta carbon were reacted with base, carbon disulfide, and methyl iodide to produce methyl 2-carboalkoxydithioalkenoate (2). These compounds were reacted with BrF3, forming the corresponding alpha-trifluoromethyl esters (3) along with 1,1-difluoro-2-trifluoromethyl-2-alkyl ethers (4). The products of type 4 have been transformed to derivatives of type 3, thus raising the overall yields of the target respective cc-trifluoromethyl esters to 65-80%. The reaction is tolerant to different functional groups such as halogens, protected alcohols, esters, and lactones.