(1S,1'S,2'S)-carboxycyclopropylglycine | 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: (1S,1'S,2'S)-carboxycyclopropylglycine
• 英文别名: (2S)-2-[(S)-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-QNVNXEQISA-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)：
  -3.4
• 重原子数：
  11
• 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：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 (1S,1'S,2'S)-carboxycyclopropylglycine
  参考文献：
  名称：

  Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogs

  摘要：

  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.

  DOI：

  10.1021/jo00013a018

文献信息

• 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。
• Facile Synthesis of (2S,1′S,2′S)-2-(Carboxycyclopropyl)glycine, an Isotype-Selective Agonist of Metabotropic Glutamate Receptors
  作者：Dawei Ma、Zhaochun Ma

  DOI：10.1016/s0040-4039(97)10037-5

  日期：1997.10

  (2S,1'S,2'S)-2-(Carboxycyclopropyl)glycine (L-CCG-I) was synthesized in 12 steps and 14% overall yield by using Sharpless's asymmetric dihydroxylation reaction and stereochemically controlled cyclopropanation as key steps. (C) 1997 Elsevier Science Ltd.

  (l-CCG-1)的合成采用了12步反应，总产率为14%。其中，应用了Sharpless不对称二羟化反应及立体化学控制下的环丙化反应作为关键步骤。
• Synthesis of trans and cis-α-(car☐ycyclopropyl)glycines. Novel neuroinhibitory amino acids as L-glutamate analogue
  作者：Keiko Yamanoi、Yasufumi Ohfune、Kazuko Watanabe、Philipp Novales Li、Hiroshi Takeuchi

  DOI：10.1016/s0040-4039(00)86682-4

  日期：1988.1