(S)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(3,4-methylenedioxy-2-trimethylsilylphenyl)methyl]isoquinoline | 439662-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (S)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(3,4-methylenedioxy-2-trimethylsilylphenyl)methyl]isoquinoline
• 英文别名: [5-[[(1S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-1,3-benzodioxol-4-yl]-trimethylsilane
• CAS: 439662-11-0
• 化学式: C₂₂H₂₉NO₄Si
• 分子量: 399.562
• InChiKey: ZGGIJJGLNMNXCP-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (S)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(3,4-methylenedioxy-2-trimethylsilylphenyl)methyl]isoquinoline 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以39%的产率得到(S)-(-)-2,3-dimethoxy-10,11-methylenedioxy-12-trimethylsilylprotoberberine
  参考文献：
  名称：

  Synthesis of protoberberines using a silyl-directed Pictet–Spengler cyclization

  摘要：

  Five naturally-occurring protoberberines have been synthesized in enantioenriched form by alkylation by two different 2-trimethylsilylbenzyl chlorides of four tetrahydroisoquinolines, derivatized with Meyers' formamidine valinol methyl ether chiral auxiliary. Silyl-directed Pictet-Spengler cyclization of the ensuing 3,4-dimethoxy-2-trimethylsilylbenzyl tetrahydroisoquinolines leads to four of the target protoberberines in excellent yield and complete regioselectivity. In the fifth case, the 3,4-methylenedioxy analog gives a mixture of protoberberine and a product of ring closure at C6 of the benzyl moiety in a 3:4 ratio. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00010-8
• 作为产物：
  描述：

  1-(dimethylamino)methyl-3,4-methylenedioxy-2-trimethylsilylbenzene 在 正丁基锂 、 氯甲酸乙酯 、 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 12.0h， 生成 (S)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(3,4-methylenedioxy-2-trimethylsilylphenyl)methyl]isoquinoline
  参考文献：
  名称：

  Synthesis of protoberberines using a silyl-directed Pictet–Spengler cyclization

  摘要：

  Five naturally-occurring protoberberines have been synthesized in enantioenriched form by alkylation by two different 2-trimethylsilylbenzyl chlorides of four tetrahydroisoquinolines, derivatized with Meyers' formamidine valinol methyl ether chiral auxiliary. Silyl-directed Pictet-Spengler cyclization of the ensuing 3,4-dimethoxy-2-trimethylsilylbenzyl tetrahydroisoquinolines leads to four of the target protoberberines in excellent yield and complete regioselectivity. In the fifth case, the 3,4-methylenedioxy analog gives a mixture of protoberberine and a product of ring closure at C6 of the benzyl moiety in a 3:4 ratio. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00010-8

文献信息

• Synthesis of protoberberines using a silyl-directed Pictet–Spengler cyclization
  作者：Paul S Cutter、R.Bryan Miller、Neil E Schore

  DOI：10.1016/s0040-4020(02)00010-8

  日期：2002.2

  Five naturally-occurring protoberberines have been synthesized in enantioenriched form by alkylation by two different 2-trimethylsilylbenzyl chlorides of four tetrahydroisoquinolines, derivatized with Meyers' formamidine valinol methyl ether chiral auxiliary. Silyl-directed Pictet-Spengler cyclization of the ensuing 3,4-dimethoxy-2-trimethylsilylbenzyl tetrahydroisoquinolines leads to four of the target protoberberines in excellent yield and complete regioselectivity. In the fifth case, the 3,4-methylenedioxy analog gives a mixture of protoberberine and a product of ring closure at C6 of the benzyl moiety in a 3:4 ratio. (C) 2002 Published by Elsevier Science Ltd.