(S)-1-(3-hydroxy-2-naphthylcarbonyl)pyrrolidine-2-carboxylic acid methyl ester | 497106-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-(3-hydroxy-2-naphthylcarbonyl)pyrrolidine-2-carboxylic acid methyl ester
• 英文别名: methyl (2S)-1-(3-hydroxynaphthalene-2-carbonyl)pyrrolidine-2-carboxylate
• CAS: 497106-69-1
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: TYDWFCHSRUOKHZ-AWEZNQCLSA-N

物化性质

• 沸点：
  500.8±45.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-(3-hydroxy-2-naphthylcarbonyl)pyrrolidine-2-carboxylic acid methyl ester 在 盐酸 、 氧气 、 copper(l) chloride 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.5h， 生成 2,2'-二羟基-1,1'-联萘-3,3'-二甲酸
  参考文献：
  名称：

  A novel method for the synthesis of (R)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid by asymmetric oxidative coupling of a chiral β-naphthol derivative catalyzed by CuCl

  摘要：

  Asymmetric oxidative coupling of (S)-1-(3-hydroxy-2-naphthylcarbonyl)pyrrolidine-2-carboxylic acid methyl ester 1 catalyzed by CuCl afforded (S,S,R)-2,2'-dihydroxy-3,3'-bis(2-methoxycarbonyl-1-pyrrolidinylcarbonyl)-1,1'-binapthalene 2 with diastereomeric excess up to 65.9%. (R)-BINOL-3,3'-diacid 3 was obtained in 30% overall yield and 97% e.e. by separating the diastereomers and hydrolyzing 2. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00507-4
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (S)-1-(3-hydroxy-2-naphthylcarbonyl)pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  A novel method for the synthesis of (R)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid by asymmetric oxidative coupling of a chiral β-naphthol derivative catalyzed by CuCl

  摘要：

  Asymmetric oxidative coupling of (S)-1-(3-hydroxy-2-naphthylcarbonyl)pyrrolidine-2-carboxylic acid methyl ester 1 catalyzed by CuCl afforded (S,S,R)-2,2'-dihydroxy-3,3'-bis(2-methoxycarbonyl-1-pyrrolidinylcarbonyl)-1,1'-binapthalene 2 with diastereomeric excess up to 65.9%. (R)-BINOL-3,3'-diacid 3 was obtained in 30% overall yield and 97% e.e. by separating the diastereomers and hydrolyzing 2. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00507-4

文献信息

• A novel method for the synthesis of (R)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid by asymmetric oxidative coupling of a chiral β-naphthol derivative catalyzed by CuCl
  作者：Zhuo-qun Xin、Chao-shan Da、Shou-liang Dong、Da-xue Liu、Jie Wei、Rui Wang

  DOI：10.1016/s0957-4166(02)00507-4

  日期：2002.9

  Asymmetric oxidative coupling of (S)-1-(3-hydroxy-2-naphthylcarbonyl)pyrrolidine-2-carboxylic acid methyl ester 1 catalyzed by CuCl afforded (S,S,R)-2,2'-dihydroxy-3,3'-bis(2-methoxycarbonyl-1-pyrrolidinylcarbonyl)-1,1'-binapthalene 2 with diastereomeric excess up to 65.9%. (R)-BINOL-3,3'-diacid 3 was obtained in 30% overall yield and 97% e.e. by separating the diastereomers and hydrolyzing 2. (C) 2002 Elsevier Science Ltd. All rights reserved.