N,N′-di(2-naphthyl)hydrazinecarboxylic acid (-)-menthyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N′-di(2-naphthyl)hydrazinecarboxylic acid (-)-menthyl ester
• 英文别名: N-(-)-menthoxycarbonyl-N,N'-di(2-naphthyl)hydrazine；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] N-naphthalen-2-yl-N-(naphthalen-2-ylamino)carbamate
• 化学式: C₃₁H₃₄N₂O₂
• 分子量: 466.623
• InChiKey: BQQRFRJHIMGBKR-ZDERHKTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N′-di(2-naphthyl)hydrazinecarboxylic acid (-)-menthyl ester 在 盐酸 、 potassium hydroxide 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 24.0h， 生成 (S)-2,2'-diamino-1,1'-binaphthalene
  参考文献：
  名称：

  An efficient and practical synthesis of BINAM derivatives by diastereoselective [3,3]-rearrangement

  摘要：

  This work describes an efficient, practical, and diastereoselective synthesis of enantiomerically pure BINAM derivatives by utilizing the acid-catalyzed [3,3]-sigmatropic rearrangement of readily accessible N-(-)-menthoxycarbonyl-diaryl hydrazines as a key step. The yield of the rearrangement is very high and two diastereomers thus obtained are easily separable. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.06.006
• 作为产物：
  描述：

  1-薄荷酰肼 在 copper(l) iodide 、 三叔丁基膦 、 palladium diacetate 、 caesium carbonate 、 4-hydroxyproline 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 生成 N,N′-di(2-naphthyl)hydrazinecarboxylic acid (-)-menthyl ester
  参考文献：
  名称：

  An efficient and practical synthesis of BINAM derivatives by diastereoselective [3,3]-rearrangement

  摘要：

  This work describes an efficient, practical, and diastereoselective synthesis of enantiomerically pure BINAM derivatives by utilizing the acid-catalyzed [3,3]-sigmatropic rearrangement of readily accessible N-(-)-menthoxycarbonyl-diaryl hydrazines as a key step. The yield of the rearrangement is very high and two diastereomers thus obtained are easily separable. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.06.006

文献信息

• An efficient and practical synthesis of BINAM derivatives by diastereoselective [3,3]-rearrangement
  作者：Bing Li、Shengyong Zhang、Weiping Chen

  DOI：10.1016/j.tetasy.2014.06.006

  日期：2014.7

  This work describes an efficient, practical, and diastereoselective synthesis of enantiomerically pure BINAM derivatives by utilizing the acid-catalyzed [3,3]-sigmatropic rearrangement of readily accessible N-(-)-menthoxycarbonyl-diaryl hydrazines as a key step. The yield of the rearrangement is very high and two diastereomers thus obtained are easily separable. (C) 2014 Elsevier Ltd. All rights reserved.