(1R,2S)-2-[(S)-carboxy-[(2-methylpropan-2-yl)oxycarbonylamino]methyl]cyclopropane-1-carboxylic acid | 117747-67-8

• 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: (1R,2S)-2-[(S)-carboxy-[(2-methylpropan-2-yl)oxycarbonylamino]methyl]cyclopropane-1-carboxylic acid
• CAS: 117747-67-8
• 化学式: C₁₁H₁₇NO₆
• 分子量: 259.259
• InChiKey: XEXZEHHDYJHEND-XVMARJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  112.93
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-[(S)-carboxy-[(2-methylpropan-2-yl)oxycarbonylamino]methyl]cyclopropane-1-carboxylic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2S,3S,4R)-α-(carboxycyclopropyl)glycine
  参考文献：
  名称：

  Shimamoto, Keiko; Ohfune, Yasufumi, Tetrahedron Letters, 1989, vol. 30, # 29, p. 3803 - 3804

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (1R,2S)-2-[(1S)-2-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]cyclopropane-1-carboxylate 在 sodium hydroxide 、 jones reagent 作用下， 以 甲醇 、 乙醚 、 丙酮 为溶剂， 生成 (1R,2S)-2-[(S)-carboxy-[(2-methylpropan-2-yl)oxycarbonylamino]methyl]cyclopropane-1-carboxylic acid
  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

• 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。
• 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
• YAMANOI, KEIKO;OHFUNE, YASUFUMI;WATANABE, KAZUKO;NOVALES, LI PHILIPP;TAKE+, TETRAHEDRON LETT., 29,(1988) N 10, 1181-1184
  作者：YAMANOI, KEIKO、OHFUNE, YASUFUMI、WATANABE, KAZUKO、NOVALES, LI PHILIPP、TAKE+

  DOI：——

  日期：——