3-[3H]-(1R,2R)-1,2-dicarbomethoxy-3-formylcyclopropane | 244076-72-0

• 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: 3-[3H]-(1R,2R)-1,2-dicarbomethoxy-3-formylcyclopropane
• 英文别名: dimethyl (1R,2R)-3-formyl-3-tritiocyclopropane-1,2-dicarboxylate
• CAS: 244076-72-0
• 化学式: C₈H₁₀O₅
• 分子量: 188.156
• InChiKey: BQLDVKLTWMNLSR-CMROSECKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  13
• 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：

  3-[3H]-(1R,2R)-1,2-dicarbomethoxy-3-formylcyclopropane 以 甲醇 为溶剂， 反应 21.0h， 生成 (2R,2'R,3'R)-N-[(R)-α-phenylglycinyl]-2-(1'-[3H]-2',3'-dicarbomethoxycyclopropyl)glycinonitrile
  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：

  (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

文献信息

• 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.