(1S)-1-[4,5-dimethoxy-2-[(R)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline | 1309831-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (1S)-1-[4,5-dimethoxy-2-[(R)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (1S)-1-[[4,5-dimethoxy-2-[(R)-(4-methylphenyl)sulfinyl]phenyl]methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS: 1309831-82-0
• 化学式: C₂₇H₃₁NO₅S
• 分子量: 481.613
• InChiKey: SNAIFXNXNMXFIQ-XSJBNIOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S)-1-[4,5-dimethoxy-2-[(R)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 在 叔丁基锂 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.25h， 以67%的产率得到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：

  2-(2-chloroethyl)-4,5-dimethoxybenzaldehyde 在 titanium(IV) tetraethanolate 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (1S)-1-[4,5-dimethoxy-2-[(R)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  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