(S)-(-)-1,2-dimethoxy-4-methyl-5-(p-tolylsulfinyl)benzene | 1309831-72-8

• 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: (S)-(-)-1,2-dimethoxy-4-methyl-5-(p-tolylsulfinyl)benzene
• 英文别名: 2-p-tolylsulfinyl-4,5-dimethoxytoluene；1,2-dimethoxy-4-methyl-5-[(S)-(4-methylphenyl)sulfinyl]benzene
• CAS: 1309831-72-8
• 化学式: C₁₆H₁₈O₃S
• 分子量: 290.383
• InChiKey: DFFBCPHSFZAHOJ-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1,2-dimethoxy-4-methyl-5-(p-tolylsulfinyl)benzene 在 叔丁基锂 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 正戊烷 为溶剂， 反应 16.25h， 生成 S-四氢罂粟碱
  参考文献：
  名称：

  Asymmetric Synthesis of (S)-(−)-Xylopinine. Use of the Sulfinyl Group as an Ipso Director in Aromatic S_E

  摘要：

  Optically pure (S)-(-)-xylopinine 2 was prepared in three steps in 52% overall yield. Thus, condensation of the carbanion derived from (S)-4 with the (S)-(E)-sulfinylimine 5 gave a 2:1 mixture of tetrahydroisoquinolines 6a and 6b, differing only in configuration at sulfur. N-Desulfinylation of this mixture gave the diastereomeric sulfoxides which, without separation, were converted into (S)-(-)-xylopinine (2) with loss of the sulfinyl moieties under Pictet-Spengler conditions. This unprecedented ipso electrophilic substitution of a sulfinyl group may have synthetic implications beyond that described in this work.

  DOI：

  10.1021/jo2007237
• 作为产物：
  描述：

  1-溴-4,5-二甲氧基-2-甲基苯 、 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.41h， 以42%的产率得到(S)-(-)-1,2-dimethoxy-4-methyl-5-(p-tolylsulfinyl)benzene
  参考文献：
  名称：

  Asymmetric Synthesis of (S)-(−)-Xylopinine. Use of the Sulfinyl Group as an Ipso Director in Aromatic S_E

  摘要：

  Optically pure (S)-(-)-xylopinine 2 was prepared in three steps in 52% overall yield. Thus, condensation of the carbanion derived from (S)-4 with the (S)-(E)-sulfinylimine 5 gave a 2:1 mixture of tetrahydroisoquinolines 6a and 6b, differing only in configuration at sulfur. N-Desulfinylation of this mixture gave the diastereomeric sulfoxides which, without separation, were converted into (S)-(-)-xylopinine (2) with loss of the sulfinyl moieties under Pictet-Spengler conditions. This unprecedented ipso electrophilic substitution of a sulfinyl group may have synthetic implications beyond that described in this work.

  DOI：

  10.1021/jo2007237

文献信息

• Asymmetric Synthesis of (<i>S</i>)-(−)-Xylopinine. Use of the Sulfinyl Group as an <i>Ipso</i> Director in Aromatic S_E
  作者：Virginia M. Mastranzo、Francisco Yuste、Benjamín Ortiz、Rubén Sánchez-Obregón、Rubén A. Toscano、José L. García Ruano

  DOI：10.1021/jo2007237

  日期：2011.6.17

  Optically pure (S)-(-)-xylopinine 2 was prepared in three steps in 52% overall yield. Thus, condensation of the carbanion derived from (S)-4 with the (S)-(E)-sulfinylimine 5 gave a 2:1 mixture of tetrahydroisoquinolines 6a and 6b, differing only in configuration at sulfur. N-Desulfinylation of this mixture gave the diastereomeric sulfoxides which, without separation, were converted into (S)-(-)-xylopinine (2) with loss of the sulfinyl moieties under Pictet-Spengler conditions. This unprecedented ipso electrophilic substitution of a sulfinyl group may have synthetic implications beyond that described in this work.