(2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine

• 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: (2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine
• 英文别名: MCCG-I；L-MCCG-I；(1S,2S)-2-[(1S)-1-amino-1-carboxyethyl]cyclopropane-1-carboxylic acid
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: KFACHLANPCGTFI-FVSJBQLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-[(3-methoxy)carbonyl-(1E)-propenyl]oxazolidin-5-one 在 palladium diacetate lithium hydroxide 、 氢溴酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 1.5h， 生成 (2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine
  参考文献：
  名称：

  Stereospecific synthesis and absolute configuration of the (2S,3S,4S)-isomer of 2-methyl-2-(carboxycyclopropyl)glycine (MCCG)

  摘要：

  The conformationally restricted metabotropic glutamate receptor antagonist (2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine 1 (MCCG) has been synthesized in a stereoselective manner (>99% ee) with the (2S 3S,4S) absolute configuration of this molecule being confirmed by X-ray crystallographic analysis. Subsequent physico-chemical studies were undertaken and the data are at odds with those of the commercially available product. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00049-1

文献信息

• Synthesis of (2S,1′ S,2′ S)-2-methyl-2-(carboxycyclopropyl)glycine and (S)-2-amino-2-methyl-4-phosphonobutyric acid from l-alanine
  作者：Dawei Ma、Zhaochun Ma、Jiqing Jiang、Zhen Yang、Chongzhi Zheng

  DOI：10.1016/s0957-4166(97)00031-1

  日期：1997.3
• Stereospecific synthesis and absolute configuration of the (2S,3S,4S)-isomer of 2-methyl-2-(carboxycyclopropyl)glycine (MCCG)
  作者：Hassan Pajouhesh、Kenneth Curry、Hossein Pajouhesh、Mahmonir H. Meresht、Brian Patrick

  DOI：10.1016/s0957-4166(03)00049-1

  日期：2003.3

  The conformationally restricted metabotropic glutamate receptor antagonist (2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine 1 (MCCG) has been synthesized in a stereoselective manner (>99% ee) with the (2S 3S,4S) absolute configuration of this molecule being confirmed by X-ray crystallographic analysis. Subsequent physico-chemical studies were undertaken and the data are at odds with those of the commercially available product. (C) 2003 Elsevier Science Ltd. All rights reserved.