1-[(1R)-1-(hydroxymethyl)prop-2-yl-1-yl]-1H-isoindole-1,3(2H)-dione | 1240283-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1-[(1R)-1-(hydroxymethyl)prop-2-yl-1-yl]-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-[(2R)-1-hydroxybut-3-yn-2-yl]isoindole-1,3-dione
• CAS: 1240283-66-2
• 化学式: C₁₂H₉NO₃
• 分子量: 215.208
• InChiKey: BYWTWQBVWSPMMS-MRVPVSSYSA-N

物化性质

• 沸点：
  413.5±35.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1-[(1R)-1-(hydroxymethyl)prop-2-yl-1-yl]-1H-isoindole-1,3(2H)-dione 在 copper(l) iodide 、 苯基溴化硒 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  A reasonably stereospecific multistep conversion of Boc-protected α-amino acids to Phth-protected β3-amino acids

  摘要：

  A method for the synthesis of beta(3)-amino acids starting from alpha-amino acids is described. This conversion can be effected by an eight-step procedure which involves the transformation of the carboxylic group into an alkyne followed by a selenium-mediated conversion of the carbon-carbon triple bond to a Se-phenyl selenocarboxylate intermediate. The reactive Se-phenyl selenocarboxylate intermediates can be trapped with water, alcohols or the amine of an amino acid derivative to give beta(3)-amino acids, beta(3)-amino esters or mixed peptides, respectively. The whole transformations of the carboxylic group into an alkyne and of the alkyne group into beta(3)-amino acids may not require purification of the intermediate products but a workup and isolation procedure of crude materials. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.143
• 作为产物：
  描述：

  N-乙氧羰基邻苯二甲酰亚胺 、 (R)-2,2-二甲基-3-(n-boc)-4-乙炔噁唑啉 在 三氟乙酸 、 sodium carbonate 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 28.0h， 以0.18 g的产率得到1-[(1R)-1-(hydroxymethyl)prop-2-yl-1-yl]-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  A reasonably stereospecific multistep conversion of Boc-protected α-amino acids to Phth-protected β3-amino acids

  摘要：

  A method for the synthesis of beta(3)-amino acids starting from alpha-amino acids is described. This conversion can be effected by an eight-step procedure which involves the transformation of the carboxylic group into an alkyne followed by a selenium-mediated conversion of the carbon-carbon triple bond to a Se-phenyl selenocarboxylate intermediate. The reactive Se-phenyl selenocarboxylate intermediates can be trapped with water, alcohols or the amine of an amino acid derivative to give beta(3)-amino acids, beta(3)-amino esters or mixed peptides, respectively. The whole transformations of the carboxylic group into an alkyne and of the alkyne group into beta(3)-amino acids may not require purification of the intermediate products but a workup and isolation procedure of crude materials. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.143

文献信息

• A reasonably stereospecific multistep conversion of Boc-protected α-amino acids to Phth-protected β3-amino acids
  作者：Andrea Temperini、Antonella Capperucci、Alessandro Degl’Innocenti、Raffaella Terlizzi、Marcello Tiecco

  DOI：10.1016/j.tetlet.2010.05.143

  日期：2010.8

  A method for the synthesis of beta(3)-amino acids starting from alpha-amino acids is described. This conversion can be effected by an eight-step procedure which involves the transformation of the carboxylic group into an alkyne followed by a selenium-mediated conversion of the carbon-carbon triple bond to a Se-phenyl selenocarboxylate intermediate. The reactive Se-phenyl selenocarboxylate intermediates can be trapped with water, alcohols or the amine of an amino acid derivative to give beta(3)-amino acids, beta(3)-amino esters or mixed peptides, respectively. The whole transformations of the carboxylic group into an alkyne and of the alkyne group into beta(3)-amino acids may not require purification of the intermediate products but a workup and isolation procedure of crude materials. (C) 2010 Elsevier Ltd. All rights reserved.