1-O-benzyl 2-O-methyl (1S,2S,6S)-6-methoxy-1-[(S)-(4-methylphenyl)sulfinyl]cyclohex-4-ene-1,2-dicarboxylate | 155687-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-benzyl 2-O-methyl (1S,2S,6S)-6-methoxy-1-[(S)-(4-methylphenyl)sulfinyl]cyclohex-4-ene-1,2-dicarboxylate
• CAS: 155687-82-4
• 化学式: C₂₄H₂₆O₆S
• 分子量: 442.533
• InChiKey: XTTPWFHKAANYJW-DLOSSFGDSA-N

物化性质

• 沸点：
  589.3±50.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-benzyl 2-O-methyl (1S,2S,6S)-6-methoxy-1-[(S)-(4-methylphenyl)sulfinyl]cyclohex-4-ene-1,2-dicarboxylate 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (S)-2-Benzyl 1-methyl 3-methoxy-1,4-cyclohexadiene-1,2-dicarboxylate
  参考文献：
  名称：

  Benzyl methyl (S)-2-(p-tolylsulfinyl)maleate: an efficient dienophile for the enantioselective synthesis of cyclohexadienes

  摘要：

  The new dienophile, benzyl methyl (S)-2-(p-tolylsulfinyl)maleate, readily prepared in two steps from benzyl acetate, reacts with a wide variety of 1,3-dienes, under catalysis by TiC4, in a very regioselective and stereoselective manner to give optically pure (ee >96%) 1,3- and/or 1,4-cyclohexadienedicarboxylate esters in very high yields.

  DOI：

  10.1021/jo00064a005
• 作为产物：
  描述：

  benzyl (R)-(+)-(p-tolylsulfinyl)acetate 在 四氢吡咯 、 碳酸氢钠 、 三乙胺 、 Eu(fod)3 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-O-benzyl 2-O-methyl (1S,2S,6S)-6-methoxy-1-[(S)-(4-methylphenyl)sulfinyl]cyclohex-4-ene-1,2-dicarboxylate
  参考文献：
  名称：

  Benzyl methyl (S)-2-(p-tolylsulfinyl)maleate: an efficient dienophile for the enantioselective synthesis of cyclohexadienes

  摘要：

  The new dienophile, benzyl methyl (S)-2-(p-tolylsulfinyl)maleate, readily prepared in two steps from benzyl acetate, reacts with a wide variety of 1,3-dienes, under catalysis by TiC4, in a very regioselective and stereoselective manner to give optically pure (ee >96%) 1,3- and/or 1,4-cyclohexadienedicarboxylate esters in very high yields.

  DOI：

  10.1021/jo00064a005

文献信息

• Benzyl methyl (S)-2-(p-tolylsulfinyl)maleate: an efficient dienophile for the enantioselective synthesis of cyclohexadienes
  作者：Ines Alonso、Juan C. Carretero、Jose L. Garcia Ruano

  DOI：10.1021/jo00064a005

  日期：1993.6

  The new dienophile, benzyl methyl (S)-2-(p-tolylsulfinyl)maleate, readily prepared in two steps from benzyl acetate, reacts with a wide variety of 1,3-dienes, under catalysis by TiC4, in a very regioselective and stereoselective manner to give optically pure (ee >96%) 1,3- and/or 1,4-cyclohexadienedicarboxylate esters in very high yields.