D-CCG-III | 125412-12-6

• 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: D-CCG-III
• 英文别名: (2R,3R,4S) α-(Carboxycyclopropyl)glycine；(1S,2R)-2-[(R)-amino(carboxy)methyl]cyclopropane-1-carboxylic acid
• CAS: 125412-12-6
• 化学式: C₆H₉NO₄
• 分子量: 159.142
• InChiKey: GZOVEPYOCJWRFC-FLRLBIABSA-N

物化性质

• 沸点：
  414.1±20.0 °C(Predicted)
• 密度：
  1.601±0.06 g/cm3(Predicted)

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：

  (1S,2R)-2-((R)-1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-cyclopropanecarboxylic acid ethyl ester 在 sodium hydroxide 、 jones reagent 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 生成 D-CCG-III
  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

• 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。
• The palladium(II)-assisted syntheses of (±)α-(methylenecyclopropyl)glycine and (±)trans-α-(carboxycyclopropyl) glycine, two bioactive amino acids.
  作者：Natsuko Kurokawa、Yasufumi Ohfune

  DOI：10.1016/s0040-4039(00)98473-9

  日期：1985.1

  Title compounds and have been synthesized efficiently from β-hydroxyallylglycine derivative via the Pd(II)-catalyzed reactions.

  标题化合物和已经被有效地从β-hydroxyallylglycine衍生物合成通过加入Pd（II） -催化的反应。
• Reactivity of (Bicyclo[5.1.0]octadienyl)iron(1+) Cations:  Application to the Synthesis of <i>cis</i>-2-(2‘-Carboxycyclopropyl)glycines
  作者：Nathaniel J. Wallock、William A. Donaldson

  DOI：10.1021/jo030259a

  日期：2004.4.1

  heteroatom nucleophiles to (bicyclo[5.1.0]octadienyl)Fe(CO)2L+ cations 5 or 8 (L = CO, PPh3) generally proceeds via attack at the dienyl terminus on the face of the ligand opposite to iron to generate 6-substituted (bicyclo[5.1.0]octa-2,4-diene)iron complexes (11 or 13). In certain cases, these products are unstable with respect to elimination of a proton and the nucleophilic substituent to afford (cyclooctatetraene)Fe(CO)2L

  碳原子和杂原子亲核试剂向（双环[5.1.0]辛二烯基）Fe（CO）2 L +阳离子5或8（L = CO，PPh 3）的加成通常是通过攻击配体表面上的二烯基末端进行的与铁相反生成六取代的（双环[5.1.0] octa-2,4-二烯）铁配合物（11或13）。在某些情况下，这些产物在消除质子和亲核取代基方面不稳定，以提供（环辛酸酯）Fe（CO）2 L（4或7）。13f的分解，是由于将邻苯二甲酰亚胺添加到8中引起的，得到N-（双环[5.1.0]八-3,5-二烯-2-基）邻苯二甲酰亚胺（19）。19（RuCl 3 / NaIO 4）的氧化裂解，然后进行酯化反应，得到环丙烷二酯22，水解后生成顺式-2-（2'-羧基环丙基）甘氨酸（CCG-III，18）（从4到43％的八个步骤）总产量）。该方法学还用于制备立体定向氘代CCG-III（d -18）和光学富集的（-）- 18。质子化22导致环丙烷开环，得到苯并吲哚并核苷（23）。
• PELLICCIARI, ROBERTO;NATALINI, BENEDETTO;MARINOZZI, MAURA;MONAHAN, JOSEPH+, TETRAHEDRON LETT., 31,(1990) N, C. 139-142
  作者：PELLICCIARI, ROBERTO、NATALINI, BENEDETTO、MARINOZZI, MAURA、MONAHAN, JOSEPH+

  DOI：——

  日期：——