(1R,2R)-3-bromo-1,2-dicarbomethoxy-3-formyl-cyclopropane | 244076-69-5

• 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-1,2-dicarbomethoxy-3-formyl-cyclopropane
• 英文别名: dimethyl (1R,2R)-3-bromo-3-formylcyclopropane-1,2-dicarboxylate
• CAS: 244076-69-5
• 化学式: C₈H₉BrO₅
• 分子量: 265.06
• InChiKey: RBUGERHTSZZZJO-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R)-3-bromo-1,2-dicarbomethoxy-3-formyl-cyclopropane 在 锌 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以yielded (1R,2R)-1,2-dicarbomethoxy-3-formyl-cyclopropane (265 mg, 88%) as a colorless oil的产率得到(1R,2R)-1,2-dicarbomethoxy-3-formyl-cyclopropane
  参考文献：
  名称：

  (2S,2'R,3'R)-2-(2,3-dicarboxyl-cyclopropyl)-glycine (DCG-1/4) and .sup.3

  摘要：

  本发明涉及式（＃STR1＃）的（2S、2'R、3'R）-2-（2,3-二羧基环丙基）-甘氨酸，其中R.sub.2是氢或氚，以及其制备过程。所述化合物可用作药理学工具，用于研究II型mGluR（代谢型谷氨酸受体）的功能。

  公开号：

  US06020525A1
• 作为产物：
  描述：

  (1S,5R,6R)-1-bromo-4-oxabicyclo[3.1.0]hexane-6-carboxylic acid 在 硫酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (1R,2R)-3-bromo-1,2-dicarbomethoxy-3-formyl-cyclopropane
  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：——
• 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
• (2S,2'R,3'R)-2-(2,3-dicarboxyl-cyclopropyl)-glycine (DCG-1/4) and .sup.3
  申请人：Hoffmann-La Roche Inc.

  公开号：US06020525A1

  公开（公告）日：2000-02-01

  This invention relates to (2S,2'R,3'R)-2-(2,3-dicarboxyl-cyclopropyl)-glycine of formula ##STR1## wherein R.sub.2 is hydrogen or tritium and to a process for the preparation thereof. The described compounds can be used as a pharmacological tool to study the function of group II mGluR (metabotropic glutamate receptor).

  这项发明涉及到式为(2S,2'R,3'R)-2-(2,3-二羧基环丙基)-甘氨酸的化合物，其中R.sub.2为氢或氚，并涉及其制备方法。所述化合物可用作研究II型mGluR（代谢型谷氨酸受体）功能的药理学工具。
• 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.