N-羟基-3,3-环戊烷戊二酰亚胺 | 64744-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 中文名称: N-羟基-3,3-环戊烷戊二酰亚胺
• 英文名称: N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione
• 英文别名: 3-Hydroxy-3-azaspiro[5.5]undecane-2,4-dione
• CAS: 64744-41-8
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: ZBAUSHIGYKKATD-UHFFFAOYSA-N

物化性质

• 沸点：
  353.8±25.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-羟基-3,3-环戊烷戊二酰亚胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 2,4-dioxo-3-azaspiro[5.5]undecan-3-yl ((benzyloxy)carbonyl)glycinate
  参考文献：
  名称：

  3-Azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate), a new reagent for the synthesis of the N-protected amino acid-ASUD ester

  摘要：

  A new reagent, 3-azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate) is described for the synthesis of N-protected amino acid-ASUD esters which are active esters useful in the synthesis of peptides. This compound was synthesized by reacting N-hydroxy-3-azaspiro[5,5]-undecane-2,4-dione (HO-ASUD) with diphenyl chlorophosphate in the presence of a base at room temperature and was obtained in high yields. The ASUD-diphenyl phosphate reagent reacts with N-protected amino acids under mild conditions to give the corresponding ASUD active esters, while preserving the enantiomeric purity of the amino acid. The new reagent is a stable crystalline compound and eliminates the need for DCC, a potent skin allergen, used previously for the synthesis of N-protected amino acid-ASUD ester. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.04.007
• 作为产物：
  描述：

  tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate 生成 N-羟基-3,3-环戊烷戊二酰亚胺
  参考文献：
  名称：

  一种用于将 boc 保护基团引入胺类的新试剂：Boc-OASUD

  摘要：

  摘要描述了一种用于制备 N-Boc-氨基酸的新试剂叔丁基 (2,4-dioxo-3-azaspiro [5,5] undecan-3-yl) 碳酸酯 (Boc-OASUD)。Boc-OASUD 在室温下在碱存在下与氨基酸及其酯反应，并以良好的产率和纯度得到 N-Boc-氨基酸及其酯。Boc 基团的引入无需外消旋化。Boc-OASUD 是一种固体且更稳定，是二碳酸二叔丁酯的更好替代品，二碳酸二叔丁酯熔点低，由于稳定​​性差，必须在塑料容器中分配，而不是玻璃。图形概要

  DOI：

  10.1080/00397911.2017.1366525

文献信息

• Process For Synthesis Of Gabapentin
  申请人：Kumar Ashok

  公开号：US20080103334A1

  公开（公告）日：2008-05-01

  A process for preparation of gabapentin comprising a step of obtaining 1,1-cyclohexane diacetic acid monoamide from 1,1-cyclohexane diacetic acid anhydride, wherein said reaction is characterized by the use of ammonia precursor or pre-generated ammonia-isopropanol solution. The invention further discloses preparation of gabapentin and isolation of gabapentin in polymorphic Form II with high yield and purity.

  制备加巴喷丁的方法包括从1,1-环己烷二乙酸酐获得1,1-环己烷二乙酸单酰胺的步骤，其中该反应的特点是使用氨的前体或预生成的氨-异丙醇溶液。该发明还揭示了加巴喷丁的制备以及高产率和纯度下的多形式II加巴喷丁的分离。
• Synthesis of dipeptides from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione activated α-amino acids
  作者：Shaik Nowshuddin、A. Ram Reddy

  DOI：10.1016/j.tetasy.2010.12.021

  日期：2011.1

  A simple two step procedure for the synthesis of a dipeptide from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) activated a-amino acids is described. In presence of DCC, N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione readily esterifies the carboxylic acid group of all the N-protected amino acids to yield crystalline N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy ester. The N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy esters of N-protected amino acids readily condensed with other amino acids and gave a dipeptide. This new method is effective for the DCC coupling of a variety of chiral amino acids without loss of enantiomeric purity. Synthesis of fifteen dipeptides including the hitherto unreported Fmoc-L-Orn(Boc)-Val-OMe. Fmoc-L-Cys(trt)-Gly-OEt and Boc-L-Tyr-Gly-OEt is presented. (C) 2011 Elsevier Ltd. All rights reserved.
• 3-Azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate), a new reagent for the synthesis of the N-protected amino acid-ASUD ester
  作者：B. Leelamaheswara Rao、Shaik Nowshuddin、Anjali Jha、Murali K. Divi、M.N.A. Rao

  DOI：10.1016/j.tetasy.2016.04.007

  日期：2016.7

  A new reagent, 3-azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate) is described for the synthesis of N-protected amino acid-ASUD esters which are active esters useful in the synthesis of peptides. This compound was synthesized by reacting N-hydroxy-3-azaspiro[5,5]-undecane-2,4-dione (HO-ASUD) with diphenyl chlorophosphate in the presence of a base at room temperature and was obtained in high yields. The ASUD-diphenyl phosphate reagent reacts with N-protected amino acids under mild conditions to give the corresponding ASUD active esters, while preserving the enantiomeric purity of the amino acid. The new reagent is a stable crystalline compound and eliminates the need for DCC, a potent skin allergen, used previously for the synthesis of N-protected amino acid-ASUD ester. (C) 2016 Elsevier Ltd. All rights reserved.
• New reagent for the introduction of Boc protecting group to amines: Boc-OASUD
  作者：B. Leela Maheswara Rao、Shaik Nowshuddin、Anjali Jha、Murali K. Divi、M. N. A. Rao

  DOI：10.1080/00397911.2017.1366525

  日期：2017.11.17

  ABSTRACT A new reagent, tert-butyl (2,4-dioxo-3-azaspiro [5,5] undecan-3-yl) carbonate (Boc-OASUD) for the preparation of N-Boc-amino acids is described. The Boc-OASUD reacts with amino acids and their esters at room temperature in the presence of a base and gives N-Boc-amino acids and their esters in good yields and purity. Introduction of the Boc group takes place without racemization. The Boc-OASUD

  摘要描述了一种用于制备 N-Boc-氨基酸的新试剂叔丁基 (2,4-dioxo-3-azaspiro [5,5] undecan-3-yl) 碳酸酯 (Boc-OASUD)。Boc-OASUD 在室温下在碱存在下与氨基酸及其酯反应，并以良好的产率和纯度得到 N-Boc-氨基酸及其酯。Boc 基团的引入无需外消旋化。Boc-OASUD 是一种固体且更稳定，是二碳酸二叔丁酯的更好替代品，二碳酸二叔丁酯熔点低，由于稳定​​性差，必须在塑料容器中分配，而不是玻璃。图形概要