(2S)-2-[[(1S)-1,2-bis(3,4-dimethoxyphenyl)ethyl]amino]-2-phenylethanol | 195311-98-9

• 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: (2S)-2-[[(1S)-1,2-bis(3,4-dimethoxyphenyl)ethyl]amino]-2-phenylethanol
• CAS: 195311-98-9
• 化学式: C₂₆H₃₁NO₅
• 分子量: 437.536
• InChiKey: LMAQLMLYPUPRJT-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-2-[[(1S)-1,2-bis(3,4-dimethoxyphenyl)ethyl]amino]-2-phenylethanol 在 草酰氯 、 二乙基异丙基胺 、 sodium cyanoborohydride 、 二甲基亚砜 作用下， 以 水 、 乙腈 为溶剂， 反应 20.75h， 生成
  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：

  L-苯甘氨醇 在 4A MS 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 9.0h， 生成 (2S)-2-[[(1S)-1,2-bis(3,4-dimethoxyphenyl)ethyl]amino]-2-phenylethanol
  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

• Chiral Amino Alcohols As Intermediates in the Stereocontrolled Synthesis of 1,3-Disubstituted Tetrahydroisoquinolines and Protoberberines
  作者：Luisa Carrillo、Dolores Badía、Esther Domínguez、Eneritz Anakabe、Iñaki Osante、Imanol Tellitu、José L. Vicario

  DOI：10.1021/jo981326h

  日期：1999.2.1

  An efficient stereocontrolled synthetic approach to (3S)-3-aryltetrahydroisoquinoline Sd and (1S,3S)-3-aryl-1-methyltetrahydroisoquinolines 3a-c by a Pictet-Spengler heterocyclization reaction of optically active (95% ee) (S)-1,2-diarylethylamines 2a-c is presented. An alternative route toward obtaining the epimeric derivative of 3a, tetrahydroisoquinoline (1R,3S)-6, was also achieved by a stereocontrolled ring opening process carried out on the oxazolotetrahydroisoquinoline 9. Tetrahydroisoquinoline 8 was employed for the stereoselective preparation of(5S,6S, 14S)-6-phenyl-2,3,10,11-tetramethoxyprotoberberin-5-ol (12), a new type of 5,6-disubstituted protoberberine derivative with excellent (d.e>95% by H-1 NMR) stereoselection.
• 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.