(1R,2S)-1-acetamide-2-indanol O-acetate | 247098-53-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1R,2S)-1-acetamide-2-indanol O-acetate
• 英文别名: (1R,2S)-1-acetamidoindan-2-yl acetate；[(1R,2S)-1-acetamido-2,3-dihydro-1H-inden-2-yl] acetate
• CAS: 247098-53-9
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: QTNJKMWNYWVJPV-QWHCGFSZSA-N

物化性质

• 沸点：
  421.7±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S)-1-acetamide-2-indanol O-acetate 在 硫酸 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 (1R,2S)-1-氨基-2-茚醇
  参考文献：
  名称：

  Lipase-mediated kinetic resolution of cis-1,2-indandiol and the Ritter reaction of its mono-acetate

  摘要：

  Lipase-mediated kinetic resolution of cis-1,2-indandiol 5 in the presence of lipase PS was examined. Enantiomerically enriched (1S,2R)-2-acetoxy-1-indanol 6a was obtained when cis-1,2-indandiol 5 was treated with one equivalent of vinyl acetate. Treatment of 5 with two equivalents of vinyl acetate furnished a mixture of (1R,2S)-2-acetoxy-1-indanol 6a and (1R,2S)-1-acetoxy-2-indanol 6b. A route to both enantiomers of a was also developed by using the enantiomerically enriched mono-acetate thus obtained. (C) 2001 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00006-4
• 作为产物：
  描述：

  (1S,2R)-1-acetamide-2-indanol O-acetate 生成 (1R,2S)-1-acetamide-2-indanol O-acetate
  参考文献：
  名称：

  Lipase-mediated resolution of cis-1-amino-2-indanol, the key component of the HIV protease inhibitor indinavir

  摘要：

  The efficient and direct resolution of cis-1-amino-2-indanol using Candida antarctica lipase B catalyzing the alcoholysis of its N,O-diacetyl derivative is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00260-8

文献信息

• 一种由酰胺酯制备二胺衍生物的方法
  申请人：上海科技大学

  公开号：CN108530381B

  公开（公告）日：2021-09-21

  本发明提供了一种由酰胺酯制备二胺衍生物的方法，其特征在于，包括对同时含有酰胺、酯官能团的酰胺酯分子中的酯基进行取代，制备二胺衍生物，所述二胺衍生物的二胺基，其中之一为保留自酰胺酯原料的羧酸酰胺。本方法原料廉价易得，催化剂用量低，反应条件简单，产物立体选择性高。
• Synthesis of enantiomers of indanoxazolidinone based on the lipase-catalyzed resolution of the corresponding N-carbamylamino derivative
  作者：Masumi Suzuki、Chiaki Nagasawa、Takeshi Sugai

  DOI：10.1016/s0040-4020(01)00454-9

  日期：2001.6

  Enantiomerically enriched (4R,5S)- and (4S,5R)-indano[1,2-d]oxazolidinones were enzymatically prepared from (+/-)-1-amino-2-indanol. Racemic 1-(N'-chloroacetyl-N-carbamylamino)-2-indanol O-chloroacetate was hydrolyzed with immobilized Pseudomonas cepacia Lipase in the presence of beta -cyclodextrin in acetone-buffer solution, to afford (1S,2R)-1-(N'-chloroacetyl-N-carbamylamino)-2-indanol (90%e.e.) and the unreacted (1R,2S)-substrate (97%e.e.), in nearly quantitative yields. The deprotection provided enantiomers of 1-N-carbamylamino-2-indanol, the precursor of indanoxazolidinone, via nitrosation-deaminocyclization reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.