(1R,2S)-(-)-2-amino-1-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethanol | 761395-52-2

• 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: (1R,2S)-(-)-2-amino-1-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethanol
• 英文别名: (1R,2S)-2-amino-1-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethanol
• CAS: 761395-52-2
• 化学式: C₁₉H₂₅NO₆
• 分子量: 363.411
• InChiKey: UAAPCQXZQHAWJU-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  92.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (1R,2S)-(-)-2-amino-1-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethanol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以77%的产率得到(1R,2S)-(-)-2-[dimethyl(2,2-dimethylethyl)-silyloxy]-2-(3,4-dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethylamine
  参考文献：
  名称：

  Asymmetric synthesis of 1,2-diaryl-2-amino ethanols

  摘要：

  A straightforward procedure for the asymmetric synthesis of 1,2-diaryl-2-amino ethanols is described. The key step relies on the diastereoselective electrophilic amination of the enolates derived from the corresponding (S,S)-(+)-pseudoephedrine arylacetamides with di-tert-butylazodicarboxylate, followed by a hydrolysis/hydrogenolysis procedure to yield alpha-amino amide derivatives with a very high degree of diastereoselection. These substrates were subsequently Subjected to a non-racemizing 1,2-addition step with several aryllithium reagents to yield the corresponding alpha-amino ketones which, upon diastereoselective reduction with NaBH4 afforded the desired beta-amino alcohols as single enantiomers with 1,2-anti relative configuration. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00181-7
• 作为产物：
  描述：

  (+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4,5-trimethoxyphenyl)acetamide 在 sodium tetrahydroborate 、 正丁基锂 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1R,2S)-(-)-2-amino-1-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethanol
  参考文献：
  名称：

  Asymmetric synthesis of 1,2-diaryl-2-amino ethanols

  摘要：

  A straightforward procedure for the asymmetric synthesis of 1,2-diaryl-2-amino ethanols is described. The key step relies on the diastereoselective electrophilic amination of the enolates derived from the corresponding (S,S)-(+)-pseudoephedrine arylacetamides with di-tert-butylazodicarboxylate, followed by a hydrolysis/hydrogenolysis procedure to yield alpha-amino amide derivatives with a very high degree of diastereoselection. These substrates were subsequently Subjected to a non-racemizing 1,2-addition step with several aryllithium reagents to yield the corresponding alpha-amino ketones which, upon diastereoselective reduction with NaBH4 afforded the desired beta-amino alcohols as single enantiomers with 1,2-anti relative configuration. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00181-7

文献信息

• A new general method for the synthesis of 4-hydroxylated 3-aryltetrahydroisoquinolines
  作者：Raúl SanMartín、Roberto Olivera、Eduardo Martínez de Marigorta、Esther Domínguez

  DOI：10.1016/0040-4020(95)00197-g

  日期：1995.5

  3-Aryl-4-hydroxytetrahydroisoquinolines have been prepared from deoxybenzoins. The nitrosation of the latter derivatives has been improved and the catalytic reduction of the obtained oximinoketones has been carried out with the help of ultrasounds. Heterocyclization to the isoquinoline moiety occurred on the unprotected 1,2-aminoalcohol to give stereoselectively the corresponding hydroxylated heterocycle

  3-芳基-4-羟基四氢异喹啉已由脱氧苯偶姻制备。后一种衍生物的亚硝化得到了改善，并且所获得的肟基酮的催化还原已经借助超声波进行了。在未保护的1,2-氨基醇上发生杂环化成异喹啉部分，从而以良好的产率立体选择性地给出了相应的羟基化杂环。
• Asymmetric synthesis of 1,2-diaryl-2-amino ethanols
  作者：Jose L. Vicario、Dolores Badı́a、Luisa Carrillo、Eneritz Anakabe

  DOI：10.1016/s0957-4166(02)00181-7

  日期：2002.5

  A straightforward procedure for the asymmetric synthesis of 1,2-diaryl-2-amino ethanols is described. The key step relies on the diastereoselective electrophilic amination of the enolates derived from the corresponding (S,S)-(+)-pseudoephedrine arylacetamides with di-tert-butylazodicarboxylate, followed by a hydrolysis/hydrogenolysis procedure to yield alpha-amino amide derivatives with a very high degree of diastereoselection. These substrates were subsequently Subjected to a non-racemizing 1,2-addition step with several aryllithium reagents to yield the corresponding alpha-amino ketones which, upon diastereoselective reduction with NaBH4 afforded the desired beta-amino alcohols as single enantiomers with 1,2-anti relative configuration. (C) 2002 Elsevier Science Ltd. All rights reserved.