(1S,5R,6R)-1-bromo-4-oxabicyclo[3.1.0]hexane-6-carboxylic acid | 263169-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,5R,6R)-1-bromo-4-oxabicyclo[3.1.0]hexane-6-carboxylic acid
• 英文别名: (1RS,5R,6R)-1-bromo-4-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid；(1S,5R,6R)-1-bromo-4-oxo-3-oxabicyclo[3.1.0]hexane-6-carboxylic acid
• CAS: 263169-43-3
• 化学式: C₆H₅BrO₄
• 分子量: 221.007
• InChiKey: SCANVLCIISWUFR-SAMGZKJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,5R,6R)-1-bromo-4-oxabicyclo[3.1.0]hexane-6-carboxylic acid 在 偶氮二异丁腈 、 tri-n-butyltin tritiide 、 硫酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 36.0h， 生成 3-[3H]-(1R,2R)-1,2-dicarbomethoxy-3-formylcyclopropane
  参考文献：
  名称：

  Synthesis of (2S,2?R,3?R)-2-(1?-[3H],2?,3?-dicarboxylcyclopropyl)-glycine ([3H]-DCG-IV)

  摘要：

  The conformationally restricted analog of L-glutamic acid (L-Glu, 1), (2S,2'R,3'R)-2-(2',3'-dicarboxylcyclopropyl)-glycine (DCG-IV, 2) is a potent group II mGluR agonist. In order to study the distribution of group IImGluRs in the brain and to establish a radioligand binding assay we have developed a synthesis of [H-3]-DCG-IV (2a). The key intermediate, alpha-bromo aldehyde 7, was prepared in four steps starting from (-)-Feist's acid (3). The incorporation of tritium was performed by reaction of 7 with tri-n-butyltin tritide to give 8, which was transformed in two steps into 2a.

  DOI：

  10.1002/(sici)1099-1344(200001)43:1<1::aid-jlcr285>3.0.co;2-n
• 作为产物：
  描述：

  (1R,2R)-3-bromo-3-(bromomethyl)cyclopropane-1,2-dicarboxylic acid 以 水 为溶剂， 反应 4.0h， 以61%的产率得到(1S,5R,6R)-1-bromo-4-oxabicyclo[3.1.0]hexane-6-carboxylic acid
  参考文献：
  名称：

  Wichmann, Juergen; Adam, Geo, European Journal of Organic Chemistry, 1999, # 11, p. 3131 - 3133

  摘要：

  DOI：

文献信息

• Wichmann, Juergen; Adam, Geo, European Journal of Organic Chemistry, 1999, # 11, p. 3131 - 3133
  作者：Wichmann, Juergen、Adam, Geo

  DOI：——

  日期：——
• Synthesis of (2S,2?R,3?R)-2-(1?-[3H],2?,3?-dicarboxylcyclopropyl)-glycine ([3H]-DCG-IV)
  作者：J�rgen Wichmann、Philipp Huguenin、Geo Adam

  DOI：10.1002/(sici)1099-1344(200001)43:1<1::aid-jlcr285>3.0.co;2-n

  日期：2000.1

  The conformationally restricted analog of L-glutamic acid (L-Glu, 1), (2S,2'R,3'R)-2-(2',3'-dicarboxylcyclopropyl)-glycine (DCG-IV, 2) is a potent group II mGluR agonist. In order to study the distribution of group IImGluRs in the brain and to establish a radioligand binding assay we have developed a synthesis of [H-3]-DCG-IV (2a). The key intermediate, alpha-bromo aldehyde 7, was prepared in four steps starting from (-)-Feist's acid (3). The incorporation of tritium was performed by reaction of 7 with tri-n-butyltin tritide to give 8, which was transformed in two steps into 2a.