(S)-2-amino-3-methoxymethyltetrahydroisoquinoline | 1616107-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (S)-2-amino-3-methoxymethyltetrahydroisoquinoline
• 英文别名: (3S)-3-(methoxymethyl)-3,4-dihydro-1H-isoquinolin-2-amine
• CAS: 1616107-81-3
• 化学式: C₁₁H₁₆N₂O
• 分子量: 192.261
• InChiKey: LGPASTNGDHSADP-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-3-methoxymethyltetrahydroisoquinoline 在 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 生成 methyl (R)-5-(((S)-3-(methoxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)imino)-3-methyl-5-phenylpentanoate
  参考文献：
  名称：

  The preparation of novel chiral auxiliaries SAMIQ/RAMIQ and their application in the asymmetric Michael addition

  摘要：

  A pair of novel chiral auxiliaries SAMIQ/RAMIQ was synthesized from L- or D-phenylalanine methyl ester hydrochloride over six steps in 45.8% and 44.4% yield, respectively. The SAMIQ-/RAMIQ-hydrazone methodology was applied for the asymmetric Michael addition of ketones to alpha,beta-unsaturated carboxylic acid methyl esters, which afforded 3-substituted-5-oxo-alkanoates in moderate to good yield (65-82%) with excellent enantioselectivity (ee=95.3%similar to>99.5%). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.049
• 作为产物：
  描述：

  (S)-(+)-α-(甲氧基甲基)苯乙胺 盐酸盐 在 盐酸 、 lithium aluminium tetrahydride 、 甲酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.0h， 生成 (S)-2-amino-3-methoxymethyltetrahydroisoquinoline
  参考文献：
  名称：

  The preparation of novel chiral auxiliaries SAMIQ/RAMIQ and their application in the asymmetric Michael addition

  摘要：

  A pair of novel chiral auxiliaries SAMIQ/RAMIQ was synthesized from L- or D-phenylalanine methyl ester hydrochloride over six steps in 45.8% and 44.4% yield, respectively. The SAMIQ-/RAMIQ-hydrazone methodology was applied for the asymmetric Michael addition of ketones to alpha,beta-unsaturated carboxylic acid methyl esters, which afforded 3-substituted-5-oxo-alkanoates in moderate to good yield (65-82%) with excellent enantioselectivity (ee=95.3%similar to>99.5%). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.049

文献信息

• The preparation of novel chiral auxiliaries SAMIQ/RAMIQ and their application in the asymmetric Michael addition
  作者：Xuan Pan、Zhanzhu Liu

  DOI：10.1016/j.tet.2014.05.049

  日期：2014.8

  A pair of novel chiral auxiliaries SAMIQ/RAMIQ was synthesized from L- or D-phenylalanine methyl ester hydrochloride over six steps in 45.8% and 44.4% yield, respectively. The SAMIQ-/RAMIQ-hydrazone methodology was applied for the asymmetric Michael addition of ketones to alpha,beta-unsaturated carboxylic acid methyl esters, which afforded 3-substituted-5-oxo-alkanoates in moderate to good yield (65-82%) with excellent enantioselectivity (ee=95.3%similar to>99.5%). (C) 2014 Elsevier Ltd. All rights reserved.