(S)-2-(Diphenyl-phosphinoyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester | 608533-83-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-(Diphenyl-phosphinoyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester
• CAS: 608533-83-1
• 化学式: C₂₃H₂₂NO₃P
• 分子量: 391.406
• InChiKey: UQWBTRKCQZOGTG-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(Diphenyl-phosphinoyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester 在 lithium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 生成 (S)-2-(Diphenyl-phosphinoyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid ((S)-1-hydroxymethyl-2-methyl-propyl)-amide
  参考文献：
  名称：

  Two-fold amino acid-based chiral aminophosphine–oxazolines and use in asymmetric allylic alkylation

  摘要：

  Chiral aminophosphine-oxazoline ligands derived from two different amino acids (tetrahydroisoquinoline carboxylic acid and proline) have been synthesized and examined as chiral auxiliaries in asymmetric allylic alkylation of three substrates. Stereoisomers la and 2a are providing the highest enantio selectivities (up to 94% ee) in the allylation of diphenylpropenyl acetate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01561-2
• 作为产物：
  描述：

  methyl (3S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate 、 二苯基次膦酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(S)-2-(Diphenyl-phosphinoyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Two-fold amino acid-based chiral aminophosphine–oxazolines and use in asymmetric allylic alkylation

  摘要：

  Chiral aminophosphine-oxazoline ligands derived from two different amino acids (tetrahydroisoquinoline carboxylic acid and proline) have been synthesized and examined as chiral auxiliaries in asymmetric allylic alkylation of three substrates. Stereoisomers la and 2a are providing the highest enantio selectivities (up to 94% ee) in the allylation of diphenylpropenyl acetate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01561-2