(3R)-3-(methoxymethyl)-1,2,3,4-tetrahydroisoquinoline | 1616107-80-2

• 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: (3R)-3-(methoxymethyl)-1,2,3,4-tetrahydroisoquinoline
• CAS: 1616107-80-2
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: IDSUOIGUQHWCCU-LLVKDONJSA-N

物化性质

• 沸点：
  274.3±20.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 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：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-3-(methoxymethyl)-1,2,3,4-tetrahydroisoquinoline 在 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 、 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成
  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：

  N-乙酰基-D-苯基丙氨酸甲酯 在 盐酸 、 锂硼氢 、 甲酸 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 mineral oil 为溶剂， 反应 49.0h， 生成 (3R)-3-(methoxymethyl)-1,2,3,4-tetrahydroisoquinoline
  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.