methyl 2-carbomethoxy-2-(2-norbornyl)-dithioethanote | 790691-92-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 2-carbomethoxy-2-(2-norbornyl)-dithioethanote
• 英文别名: Methyl 2-(2-bicyclo[2.2.1]heptanyl)-3-methylsulfanyl-3-sulfanylidenepropanoate
• CAS: 790691-92-8
• 化学式: C₁₂H₁₈O₂S₂
• 分子量: 258.406
• InChiKey: CXIXCJULPPCJNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• 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：

  methyl 2-carbomethoxy-2-(2-norbornyl)-dithioethanote 在 盐酸 、 甲醇 、 三氟化溴 、 氢氟酸 作用下， 以 一氟三氯甲烷 、 水 为溶剂， 反应 14.0h， 生成 methyl 2-(2-norbornyl)-2-trifluoromethylethanoate
  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 、 methyl 2-norbornylacetate 、 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methyl 2-carbomethoxy-2-(2-norbornyl)-dithioethanote
  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