(+)-(1S)-N-(2,2-diethoxyethyl)-1,2-bis(3,4-dimethoxyphenyl)-N-methylethylamine | 195311-95-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (+)-(1S)-N-(2,2-diethoxyethyl)-1,2-bis(3,4-dimethoxyphenyl)-N-methylethylamine
• 英文别名: (1S)-N-(2,2-diethoxyethyl)-1,2-bis(3,4-dimethoxyphenyl)-N-methylethanamine
• CAS: 195311-95-6
• 化学式: C₂₅H₃₇NO₆
• 分子量: 447.572
• InChiKey: YIEGWWLWXMPHAV-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-(1S)-N-(2,2-diethoxyethyl)-1,2-bis(3,4-dimethoxyphenyl)-N-methylethylamine 在 盐酸 作用下， 生成 (-)-(1S,4R)-6,7-dimethoxy-1-(3,4-dimethoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol 、 (+)-(1S,4S)-6,7-dimethoxy-1-(3,4-dimethoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol
  参考文献：
  名称：

  Stereochemical studies on the synthesis of 1,2,3,4-tetrahydroisoquinolin-4-ols

  摘要：

  The stereoselectivity of the acid catalyzed promoted cyclization of adequately substituted alpha-aminoaldehydes to afford a series of tetrahydroisoquinolin-4-ols is studied. The results illustrate the effect of the substituents at C-l and/or C-3 in the target heterocycle. The required precursors 5 and 10 were synthesized from the enantiomerically pure (-)-imines 1 by two different routes, and reacted with cone. HCl. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00164-5
• 作为产物：
  描述：

  [1,2-Bis-(3,4-dimethoxy-phenyl)-ethyl]-methyl-amine 、 2-溴-1,1-二乙氧基乙烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 72.0h， 生成 (+)-(1S)-N-(2,2-diethoxyethyl)-1,2-bis(3,4-dimethoxyphenyl)-N-methylethylamine 、 (-)-(1R)-N-(2,2-diethoxyethyl)-1,2-bis(3,4-dimethoxyphenyl)-N-methylethylamine
  参考文献：
  名称：

  A Simple and Efficient Synthetic Route to Chiral Isopavines. Synthesis of (−)-O-Methylthalisopavine and (−)-Amurensinine

  摘要：

  The isopavinan alkaloids (-)-O-methylthalisopavine (7a) and (-)-amurensinine (7d) have been synthesized in good yield and high ee from the appropriate 1,2-diarylethylamine derivatives using optically active beta-amino alcohols as chiral support. This synthetic route employs as key steps the alkylation reaction of the azomethine derivatives 2 with Grignard reagents 1 and a novel one-pot double-intramolecular cyclization of the adequately functionalized 1,2-diarylethylamines 5 to afford a series of optically active isopavines 6a-d and 7a-d.

  DOI：

  10.1021/jo9708102

文献信息

• Stereoselective Synthesis of Aporphine Alkaloids Using a Hypervalent Iodine­(III) Reagent-Promoted Oxidative Nonphenolic Biaryl Coupling Reaction­. Total Synthesis of (<i>S</i>)-(+)-Glaucine
  作者：Dolores Badía、Eneritz Anakabe、Luisa Carrillo、Jose L. Vicario、Maite Villegas

  DOI：10.1055/s-2004-816009

  日期：——

  hydrogenation led to the key intermediate, optically active, 1-benzyltetrahydroisoquinolines 7a-c. The final C-ring closure step was performed by C-C biaryl bond formation by an hypervalent iodine(III) reagent promoted oxidative coupling, affording the target heterocycles 8a-c in good yields and with no racemization at the formerly created stereogenic center.

  由适当的 1,2-二芳基乙胺衍生物（依次使用 (S)-(+) -苯基甘氨醇作为手性载体。接下来，一系列简单的转化：用溴乙醛二乙缩醛进行 N-烷基化、N-甲基化、Pommeranz-Fritsch 环化和离子加氢，得到关键的中间体、光学活性的 1-苄基四氢异喹啉 7a-c。最后的 C 环闭合步骤是通过高价碘 (III) 试剂形成的 CC 联芳键进行的，促进氧化偶联，以良好的收率提供目标杂环 8a-c，并且在以前创建的立体中心没有外消旋化。
• A Simple and Efficient Synthetic Route to Chiral Isopavines. Synthesis of (−)-<i>O</i>-Methylthalisopavine and (−)-Amurensinine
  作者：Luisa Carrillo、Dolores Badía、Esther Domínguez、José L. Vicario、Imanol Tellitu

  DOI：10.1021/jo9708102

  日期：1997.10.1

  The isopavinan alkaloids (-)-O-methylthalisopavine (7a) and (-)-amurensinine (7d) have been synthesized in good yield and high ee from the appropriate 1,2-diarylethylamine derivatives using optically active beta-amino alcohols as chiral support. This synthetic route employs as key steps the alkylation reaction of the azomethine derivatives 2 with Grignard reagents 1 and a novel one-pot double-intramolecular cyclization of the adequately functionalized 1,2-diarylethylamines 5 to afford a series of optically active isopavines 6a-d and 7a-d.
• Stereochemical studies on the synthesis of 1,2,3,4-tetrahydroisoquinolin-4-ols
  作者：Luisa Carrillo、Dolores Badı́a、Esther Domı́nguez、Imanol Tellitu、José Luis Vicario

  DOI：10.1016/s0957-4166(98)00164-5

  日期：1998.5

  The stereoselectivity of the acid catalyzed promoted cyclization of adequately substituted alpha-aminoaldehydes to afford a series of tetrahydroisoquinolin-4-ols is studied. The results illustrate the effect of the substituents at C-l and/or C-3 in the target heterocycle. The required precursors 5 and 10 were synthesized from the enantiomerically pure (-)-imines 1 by two different routes, and reacted with cone. HCl. (C) 1998 Elsevier Science Ltd. All rights reserved.