(S,S,S)-2,2'-dihydroxy-3,3'-bis(2-methoxycarbonyl-1-pyrrolidinylcarbonyl)-1,1'-binaphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S,S,S)-2,2'-dihydroxy-3,3'-bis(2-methoxycarbonyl-1-pyrrolidinylcarbonyl)-1,1'-binaphthalene
• 英文别名: (S,S,R)-2,2-dihydroxy-3,3'-bis(2-methoxycarbonyl-1-pyrrolidinylcarbonyl)-1,1'-binaphthalene；methyl (2S)-1-[3-hydroxy-4-[2-hydroxy-3-[(2S)-2-methoxycarbonylpyrrolidine-1-carbonyl]naphthalen-1-yl]naphthalene-2-carbonyl]pyrrolidine-2-carboxylate
• 化学式: C₃₄H₃₂N₂O₈
• 分子量: 596.637
• InChiKey: HVRFZJFVDXSFOZ-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  44
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S,S,S)-2,2'-dihydroxy-3,3'-bis(2-methoxycarbonyl-1-pyrrolidinylcarbonyl)-1,1'-binaphthalene 在 盐酸 作用下， 反应 0.5h， 以74%的产率得到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：

  3-羟基-2-萘甲酰氯 在 氧气 、 三乙胺 、 copper(l) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 52.0h， 生成 (S,S,S)-2,2'-dihydroxy-3,3'-bis(2-methoxycarbonyl-1-pyrrolidinylcarbonyl)-1,1'-binaphthalene
  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.