Dithiobenzoic acid (1R,4R)-7,7-dimethyl-2-thioxo-bicyclo[2.2.1]hept-1-ylmethyl ester | 186391-65-1

• 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: Dithiobenzoic acid (1R,4R)-7,7-dimethyl-2-thioxo-bicyclo[2.2.1]hept-1-ylmethyl ester
• CAS: 186391-65-1
• 化学式: C₁₇H₂₀S₃
• 分子量: 320.544
• InChiKey: MKCNFATWKFFKAU-CXAGYDPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Dithiobenzoic acid (1R,4R)-7,7-dimethyl-2-thioxo-bicyclo[2.2.1]hept-1-ylmethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 25.0h， 生成 (1R,2R,4R)-1-mercaptomethyl-7,7-dimethylbicyclo[2.2.1]heptane-2-thiol
  参考文献：
  名称：

  New camphor-derived sulfur chiral controllers: Synthesis of (2R-exo)-10-methylthio-2-bornanethiol and (2R-exo)-2,10-bis(methylthio)bornane

  摘要：

  An efficient preparation of two camphor-derived controllers [(2R-exo)-10-methylthio-2-bornanethiol 1b and (2R-exo)-2,10-bis(methylthio)bornane 2] potentially useful as a ligands or chiral auxiliaries in asymmetric synthesis is described. Both compounds have been prepared starting from (1S)-camphor-10-thiol 3. Alkylation of this thiol with sodium methoxide and methyl iodide afforded 10-methylthiocamphor 8. Conversion of 8 into the corresponding thioketone 9 with the Lawesson's reagent followed by the stereoselective reduction with DIBAL-H at low temperature yielded (2R-exo)-10-methylthio-2-bornanethiol 1b in good yield. (2R-exo)-2,10-bis(Methylthio)bornane 2 could be obtained by alkylation of 1b with sodium methoxide and methyl iodide. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00463-6
• 作为产物：
  描述：

  (1S,4R)-camphor-10-thiol 在 劳森试剂 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.5h， 生成 Dithiobenzoic acid (1R,4R)-7,7-dimethyl-2-thioxo-bicyclo[2.2.1]hept-1-ylmethyl ester
  参考文献：
  名称：

  New camphor-derived sulfur chiral controllers: Synthesis of (2R-exo)-10-methylthio-2-bornanethiol and (2R-exo)-2,10-bis(methylthio)bornane

  摘要：

  An efficient preparation of two camphor-derived controllers [(2R-exo)-10-methylthio-2-bornanethiol 1b and (2R-exo)-2,10-bis(methylthio)bornane 2] potentially useful as a ligands or chiral auxiliaries in asymmetric synthesis is described. Both compounds have been prepared starting from (1S)-camphor-10-thiol 3. Alkylation of this thiol with sodium methoxide and methyl iodide afforded 10-methylthiocamphor 8. Conversion of 8 into the corresponding thioketone 9 with the Lawesson's reagent followed by the stereoselective reduction with DIBAL-H at low temperature yielded (2R-exo)-10-methylthio-2-bornanethiol 1b in good yield. (2R-exo)-2,10-bis(Methylthio)bornane 2 could be obtained by alkylation of 1b with sodium methoxide and methyl iodide. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00463-6