N-carbobenzyloxy-(1R,2S)-cis-1-amino-2-indanol | 244128-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-carbobenzyloxy-(1R,2S)-cis-1-amino-2-indanol
• 英文别名: benzyl (1R,2S)-N-(1-hydroxyindan-2-yl)carbamate；benzyl N-[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamate
• CAS: 244128-37-8
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: PJHDVFVGPKCGQX-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-carbobenzyloxy-(1R,2S)-cis-1-amino-2-indanol 、 (+/-)-α-cyano-α-fluoro-p-tolylacetyl chloride 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以2.58 g的产率得到(S)-Cyano-fluoro-p-tolyl-acetic acid (1R,2S)-1-benzyloxycarbonylamino-indan-2-yl ester
  参考文献：
  名称：

  An efficient procedure for the resolution of α-cyano-α-fluoro-p-tolylacetic acid (CFTA) via the diastereomeric N-carbobenzyloxy-cis-1-amino-2-indanol esters

  摘要：

  Development of a new, efficient resolution method of alpha-cyano-alpha-fluoro-p-tolylacetic acid (CFTA) 2a has been successfully achieved, which has been troublesome to obtain by conventional methods, in spite of its outstanding ability as an NMR chiral derivatizing agent. Fractional recrystallization of a mixture of the diastereomeric CFTA esters prepared from racemic CFTA chloride and (1R,2S)-N-carbobenzyloxy-cis-1-amino-2-indanol (-)-B afforded the less-soluble diastereomer, which was hydrolyzed to give (S)-2a. It has also been demonstrated that optically active N-acetyl-cis-1-amino-2-indanol is effective for the chromatographic resolution of alpha-arylacetic acids including ibuprofen and naproxen. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.024
• 作为产物：
  描述：

  (1S,2R)-(-)-1-氨基-2-茚醇 在 sodium carbonate 作用下， 反应 6.0h， 生成 N-carbobenzyloxy-(1R,2S)-cis-1-amino-2-indanol
  参考文献：
  名称：

  Enzymatic resolution of (±)-cis- and (±)-trans-1-aminoindan-2-ol and (±)-cis- and (±)-trans-2-aminoindan-1-ol

  摘要：

  Pseudomonas cepacia lipase (PSL) efficiently catalyses the kinetic resolution of (+/-)-cis- and (+/-)-trans-1-aminoindan-2-ol through the O-acylation reaction of the corresponding N-benzyloxycarbonyl derivative using vinyl acetate as the acyl donor. In a similar way, cis-N-Cbz-2-aminoindan-1-ol is resolved when isopropenyl acetate is used as the acylating agent. The enantioselectivity of the reaction was lower for (+/-)-trans-N-Cbz-2-aminoindan-1-ol due to the different steric requirements for the two conformers of this substrate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00200-1

文献信息

• Enzymatic resolution of (±)-cis- and (±)-trans-1-aminoindan-2-ol and (±)-cis- and (±)-trans-2-aminoindan-1-ol
  作者：Amparo Luna、Alicia Maestro、Covadonga Astorga、Vicente Gotor

  DOI：10.1016/s0957-4166(99)00200-1

  日期：1999.5

  Pseudomonas cepacia lipase (PSL) efficiently catalyses the kinetic resolution of (+/-)-cis- and (+/-)-trans-1-aminoindan-2-ol through the O-acylation reaction of the corresponding N-benzyloxycarbonyl derivative using vinyl acetate as the acyl donor. In a similar way, cis-N-Cbz-2-aminoindan-1-ol is resolved when isopropenyl acetate is used as the acylating agent. The enantioselectivity of the reaction was lower for (+/-)-trans-N-Cbz-2-aminoindan-1-ol due to the different steric requirements for the two conformers of this substrate. (C) 1999 Elsevier Science Ltd. All rights reserved.
• An efficient procedure for the resolution of α-cyano-α-fluoro-p-tolylacetic acid (CFTA) via the diastereomeric N-carbobenzyloxy-cis-1-amino-2-indanol esters
  作者：Tomoya Fujiwara、Masaki Sasaki、Kenji Omata、Chizuko Kabuto、Kuninobu Kabuto、Yoshio Takeuchi

  DOI：10.1016/j.tetasy.2003.12.024

  日期：2004.2

  Development of a new, efficient resolution method of alpha-cyano-alpha-fluoro-p-tolylacetic acid (CFTA) 2a has been successfully achieved, which has been troublesome to obtain by conventional methods, in spite of its outstanding ability as an NMR chiral derivatizing agent. Fractional recrystallization of a mixture of the diastereomeric CFTA esters prepared from racemic CFTA chloride and (1R,2S)-N-carbobenzyloxy-cis-1-amino-2-indanol (-)-B afforded the less-soluble diastereomer, which was hydrolyzed to give (S)-2a. It has also been demonstrated that optically active N-acetyl-cis-1-amino-2-indanol is effective for the chromatographic resolution of alpha-arylacetic acids including ibuprofen and naproxen. (C) 2003 Elsevier Ltd. All rights reserved.