(3aS,4aR,7R,8aS)-1-benzyl-8-oxo-octahydro-2-oxa-1,7a-diaza-s-indacene-7-carboxylic acid tert-butyl ester | 851544-45-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3aS,4aR,7R,8aS)-1-benzyl-8-oxo-octahydro-2-oxa-1,7a-diaza-s-indacene-7-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (3aS,4aR,7S,9aS)-1-benzyl-9-oxo-3,3a,4,4a,5,6,7,9a-octahydro-[1,2]oxazolo[3,4-f]indolizine-7-carboxylate
• CAS: 851544-45-1
• 化学式: C₂₁H₂₈N₂O₄
• 分子量: 372.464
• InChiKey: WCGJTBGBRCOAEU-BDXSIMOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,4aR,7R,8aS)-1-benzyl-8-oxo-octahydro-2-oxa-1,7a-diaza-s-indacene-7-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以99%的产率得到(3S,4S,6R,9S)-3-amino-1-aza-2-oxo-4-hydroxymethyl-bicyclo[4.3.0]nonanecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Functionalized Azabicycloalkane Amino Acids by Nitrone 1,3-Dipolar Intramolecular Cycloaddition

  摘要：

  An efficient and operationally simple method for the synthesis of functionalized azaoxobicyclo[X.3.0]alkane amino acids has been devised. The key step is an intramolecular nitrone cycloaddition on 5-allyl- or 5-homoallylproline that was found to be completely regio- and stereoselective.

  DOI：

  10.1021/jo0500683
• 作为产物：
  描述：

  (2R,5S)-5-allyl-1-methoxyoxalylpyrrolidine-2-carboxylic acid tert-butyl ester 在 锂硼氢 、 草酰氯 、 碳酸氢钠 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 (3aS,4aR,7R,8aS)-1-benzyl-8-oxo-octahydro-2-oxa-1,7a-diaza-s-indacene-7-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Functionalized Azabicycloalkane Amino Acids by Nitrone 1,3-Dipolar Intramolecular Cycloaddition

  摘要：

  An efficient and operationally simple method for the synthesis of functionalized azaoxobicyclo[X.3.0]alkane amino acids has been devised. The key step is an intramolecular nitrone cycloaddition on 5-allyl- or 5-homoallylproline that was found to be completely regio- and stereoselective.

  DOI：

  10.1021/jo0500683

文献信息

• Peptidomimetic Compounds and Preparation of Biologically Active Derivatives
  申请人：Scolastico Carlo

  公开号：US20080139461A1

  公开（公告）日：2008-06-12

  The invention relates to novel cyclic peptidomimetic compounds containing the sequence RGD for the preparation of appropriately functionalised antagonists of αvβ3 and αvβ5 integrins, and intended, for example, for the treatment of altered angiogenic phenomena or for the preparation of diagnostically useful compounds.
• Functionalized Azabicycloalkane Amino Acids by Nitrone 1,3-Dipolar Intramolecular Cycloaddition
  作者：Leonardo Manzoni、Daniela Arosio、Laura Belvisi、Antonio Bracci、Matteo Colombo、Donatella Invernizzi、Carlo Scolastico

  DOI：10.1021/jo0500683

  日期：2005.5.1

  An efficient and operationally simple method for the synthesis of functionalized azaoxobicyclo[X.3.0]alkane amino acids has been devised. The key step is an intramolecular nitrone cycloaddition on 5-allyl- or 5-homoallylproline that was found to be completely regio- and stereoselective.