(2R,3'R)-4-[3-methoxycarbonyl-2-(1',2',3',4'-tetrahydroquinolin-3'-yl)propyl]piperidine-1-carboxylic acid tert-butyl ester | 791820-88-7

• 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: (2R,3'R)-4-[3-methoxycarbonyl-2-(1',2',3',4'-tetrahydroquinolin-3'-yl)propyl]piperidine-1-carboxylic acid tert-butyl ester
• CAS: 791820-88-7
• 化学式: C₂₄H₃₆N₂O₄
• 分子量: 416.561
• InChiKey: LNYREZFRWFJOJC-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (2,3-Z)-4-(3-methoxycarbonyl-2-quinolin-3-yl-allyl)piperidine-1-carboxylic acid tert-butyl ester 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 氢气 、 碘 作用下， 以 乙酸乙酯 为溶剂， 65.0 ℃ 、2.5 MPa 条件下， 反应 91.0h， 生成 (2S,3'R)-4-[3-methoxycarbonyl-2-(1',2',3',4'-tetrahydroquinolin-3'-yl)propyl]piperidine-1-carboxylic acid tert-butyl ester 、 (2S,3'S)-4-[3-methoxycarbonyl-2-(1',2',3',4'-tetrahydroquinolin-3'-yl)propyl]piperidine-1-carboxylic acid tert-butyl ester 、 (2R,3'R)-4-[3-methoxycarbonyl-2-(1',2',3',4'-tetrahydroquinolin-3'-yl)propyl]piperidine-1-carboxylic acid tert-butyl ester 、 tert-butyl 4-[(2R)-4-methoxy-4-oxo-2-[(3S)-1,2,3,4-tetrahydroquinolin-3-yl]butyl]piperidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of an αvβ3 integrin antagonist intermediate via asymmetric hydrogenation of an α,β-unsaturated ester with BoPhoz-iridium and BoPhoz-rhodium catalysts

  摘要：

  The enantioselective synthesis of an alpha(v)beta(3) integrin antagonist intermediate was approached via asymmetric hydrogenation of a beta,beta-disubstituted-alpha,beta-unsaturated ester. As a result of the rapid parallel screening of a selection of ligands and catalysts, we found that neutral Me-BoPhoz-rhodium and iridium catalysts effect the required transformation with a high enantioselectivity. Both the activity and selectivity of the catalysts were strongly dependent on the choice of solvent and counter-ion. The addition of iodine modified the iridium catalyst such that the reduction of the 3-substituted quinoline ring took place. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.031