(2R,3R,4R) α-(Carboxycyclopropyl)glycine | 22255-17-0

• 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: (2R,3R,4R) α-(Carboxycyclopropyl)glycine
• 英文别名: (2S)-2-[(R)-amino(carboxy)methyl]cyclopropane-1-carboxylic acid
• CAS: 22255-17-0；95673-12-4；104758-69-2；104758-70-5；117857-93-9；117857-94-0；117857-95-1；117857-96-2；125412-10-4；125412-11-5；125412-12-6；125412-13-7；129446-08-8
• 化学式: C₆H₉NO₄
• 分子量: 159.142
• InChiKey: GZOVEPYOCJWRFC-UQBUZFSFSA-N

物化性质

• 熔点：
  243-245 °C (decomp)
• 沸点：
  414.1±20.0 °C(Predicted)
• 密度：
  1.601±0.06 g/cm3(Predicted)
• 溶解度：
  H2O:>7 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  -0.88
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  100.62
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  C-[(R)-C-Furan-2-yl-C-((1S,2S)-2-furan-2-yl-cyclopropyl)]-methylamine 在 臭氧 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以93%的产率得到(2R,3R,4R) α-(Carboxycyclopropyl)glycine
  参考文献：
  名称：

  的新颖的对映选择性合成反式-α-（2- carboxycycloprop -1-基）甘氨酸：构象受限L-谷氨酸类似物

  摘要：

  由反式-1,3-二（2-呋喃基）丙烯酮合成d-和l-α-（2-羧基环丙-1-基）甘氨酸。将双键转化为环丙烷，然后形成肟醚。肟醚的对映选择性还原，非对映异构体的分离和呋喃环的氧化，得到对映体纯的d-和I-CCG I和CCG II。通过X射线晶体结构分析确定肟7b的结构。关键步骤是恶唑硼烷催化的肟醚向胺的对映选择性转化。

  DOI：

  10.1016/s0957-4166(98)00061-5

文献信息

• D-3,4-‘cyclopropylglutamate’ isomers as nmda receptor ligands: Synthesis and enantioselective activity.
  作者：Roberto Pellicciari、Benedetto Natalini、Maura Marinozzi、Joseph B Monahan、James P Snyder

  DOI：10.1016/s0040-4039(00)94355-7

  日期：1990.1

  D-Cbz-vinylglycine methyl ester (11) afforded a mixture of the cyclopropyl esters D-CGA A-D (13) from which the corresponding 2R-acids 7-10 were obtained and their absolute configurations assigned. The (2R,3S,4R) α-(carboxycyclopropyl)glycine (D-CGA C, 9 resulted to be the most potent and selective among the NMDA receptor ligands yet reported.

  二铑（II）四乙酸催化在d-CBZ-乙烯基甘氨酸甲基酯的存在重氮乙酸乙酯的分解（11） ，得到环丙基酯d-CGA AD的混合物（13），从该相应2R酸7-10得到及其绝对配置。结果表明，（2R，3S，4R）α-（羧基环丙基）甘氨酸（D-CGA C，9）在迄今为止报道的NMDA受体配体中是最有效和最具选择性的。
• Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogs
  作者：Keiko Shimamoto、Michiko Ishida、Haruhikio Shinozaki、Yasufumi Ohfune

  DOI：10.1021/jo00013a018

  日期：1991.6

  To determine what conformations of L-glutamate (L-Glu) activate that compound's different receptors in the mammalian central nervous system, four diastereomeric L-2-(carboxycyclopropyl)glycines, 1-4, which are conformationally constrained analogues of the extended and folded conformers of L-Glu, were synthesized and subjected to neutrophysiological assay. Compounds 1-4 were efficiently synthesized from chiral amino acids. Cyclopropanation of the (2S)-2-amino-3-butenol derivative 5b gave intermediates for the synthesis of all four diastereomers. Stereoselective cyclopropanation of both the alpha,beta-unsaturated gamma-lactam 16 and the delta-lactone 19 gave precursors of (2S,1'S,2'R)-3 and (2S,1'R,2'S)-4, respectively. Neurophysiological assays of 1-4 performed with the newborn rat spinal cord demonstrated that the compounds induced a variety of depolarizing effects. The results of the assays strongly suggested that the N-methyl-D-aspartic acid (NMDA) receptor is activated by the folded conformer of L-Glu and that the extended conformer of L-Glu activates the metabotropic L-Glu receptor. The four analogous D-2-(carboxycyclopropyl)glycines (D-1-D-4), which were synthesized from (2R)-5b, proved to be NMDA agonists.
• Novel enantioselective synthesis of trans-α-(2-carboxycycloprop-1-yl)glycines: conformationally constrained l-glutamate analogues
  作者：Ayhan S Demir、Cihangir Tanyeli、Ali Cagir、M.Nawaz Tahir、Dincer Ulku

  DOI：10.1016/s0957-4166(98)00061-5

  日期：1998.3

  followed by the formation of an oxime ether. Enantioselective reduction of the oxime ether, separation of diastereomers and oxidation of the furane rings gave enantiomerically pure d- and l-CCG I and CCG II. The structure of oxime 7b was determined by X-ray crystal structure analysis. The key step is the oxazaborolidine catalyzed enantioselective conversion of oxime ethers to amines.

  由反式-1,3-二（2-呋喃基）丙烯酮合成d-和l-α-（2-羧基环丙-1-基）甘氨酸。将双键转化为环丙烷，然后形成肟醚。肟醚的对映选择性还原，非对映异构体的分离和呋喃环的氧化，得到对映体纯的d-和I-CCG I和CCG II。通过X射线晶体结构分析确定肟7b的结构。关键步骤是恶唑硼烷催化的肟醚向胺的对映选择性转化。