(R)-2-(5-oxotetrahydrofuran-3-yl)isoindoline-1,3-dione | 1240283-76-4

• 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: (R)-2-(5-oxotetrahydrofuran-3-yl)isoindoline-1,3-dione
• 英文别名: 2-[(3R)-5-oxotetrahydrofuran-3-yl]-1H-isoindole-1,3(2H)-dione；2-[(3R)-5-oxooxolan-3-yl]isoindole-1,3-dione
• CAS: 1240283-76-4
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: VWMWWMHTIKBOJA-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以0.07 g的产率得到(R)-2-(5-oxotetrahydrofuran-3-yl)isoindoline-1,3-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

• Radical Decarboxylative Cyanomethylation of Aliphatic Carboxylic Acids and Uronic Acids via Vinyl Azide Cascade Fragmentation
  作者：Linhua Xu、Qishuai Li、Dongwei Li、Xin Zhou、Ni Song、Peng Wang、Ming Li

  DOI：10.1002/cjoc.202200732

  日期：——

  A direct oxidative radical decarboxylative cyanomethylation of carboxylic acids is described using 3-azido-2-methylbut-3-en-2-ol as the carbon-centered radical acceptor. The transformation is applicable to structurally diverse α-amino acids, α-oxy acids, α-keto acids, pentofuranuronic acids, and hexopyranuronic acids. The mechanistic investigations suggest that a radical process is involved in the

  使用 3-azido-2-methylbut-3-en-2-ol 作为以碳为中心的自由基受体，描述了羧酸的直接氧化自由基脱羧氰甲基化。该转化适用于结构多样的α-氨基酸、α-含氧酸、α-酮酸、戊呋喃糖醛酸和己吡喃糖醛酸。机械研究表明，转变涉及一个激进的过程。这项工作为构建具有生物学相关性的β-氨基酸、5-脱氧-己呋喃糖和 6-脱氧-庚糖提供了一种潜在的方法。