(1R,2R)-3-bromo-3-(bromomethyl)cyclopropane-1,2-dicarboxylic acid | 244076-66-2

• 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: (1R,2R)-3-bromo-3-(bromomethyl)cyclopropane-1,2-dicarboxylic acid
• 英文别名: (1R,2R)-3-bromomethyl-cyclopropane-1,2-dicarboxylic acid；3-Brom-3-brommethyl-cyclopropan-trans-1.2-dicarbonsaeure
• CAS: 244076-66-2
• 化学式: C₆H₆Br₂O₄
• 分子量: 301.919
• InChiKey: YWURKUHKITZMCF-PWNYCUMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  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：
• 作为产物：
  描述：

  Feist's acid 在 溴 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以64%的产率得到(1R,2R)-3-bromo-3-(bromomethyl)cyclopropane-1,2-dicarboxylic acid
  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

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：——
• STRUCTURE OF FEIST'S METHYLCYCLOPROPENE-DICARBOXYLIC ACID
  作者：Martin G. Ettlinger

  DOI：10.1021/ja01142a537

  日期：1952.11
• A PROCESS FOR THE MANUFACTURE OF (2S,2'R,3'R)-2-(2,3-DICARBOXYLCYCLOPROPYL)-GLYCINE
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1064255B1

  公开（公告）日：2004-05-26
• US6020525A
  申请人：——

  公开号：US6020525A

  公开（公告）日：2000-02-01
• 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.