1-氨基-2-苯基环丙烷羧酸 | 129101-41-3

• 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
• 中文名称: 1-氨基-2-苯基环丙烷羧酸
• 英文名称: (1R,2R)-1-amino-2-phenylcyclopropanecarboxylic acid
• 英文别名: (+)-1-amino-2-phenyl-cyclopropanecarboxylic acid；(2R,3R)-2,3-methanophenylalanine；Cyclopropanecarboxylic acid, 1-amino-2-phenyl-, (1R,2R)-；(1R,2R)-1-amino-2-phenylcyclopropane-1-carboxylic acid
• CAS: 129101-41-3
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: MRUPFDZGTJQLCH-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 1-氨基-2-苯基环丙烷羧酸 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Comparison of the Effects of (2S,3S)-2,3-Methanomethionine, (2R,3R)-2,3-Methanomethionine, and (2R,3R)-2,3-Methanophenylalanine on the Conformations of Small Peptides

  摘要：

  The goal of this paper is to lay foundations for an understanding of the local conformational effects of 2,3-methanoamino acids on secondary structures. These studies are a necessary preliminary to the anticipated applications of 2,3-methanoamino acids in rational manipulation of peptidomimetic and protein-mimic conformations. Derails of the research described are as follows. Quenched molecular dynamics (QMD) studies have been performed to compare the conformational effects of (2S,3S)-2,3 -methanomethionine (2S,3S-cyclo-M), (2R,3R)-2,3 -methanomethionine (2R,3R-cyclo-M), and (2R,3R)-2,3-methanophenylalanine (2R,3R-cyclo-F) incorporated into small peptide systems. Data generated for F{2R,3R-cyclo-M}RF-NH2 and F{2S,3S-cyclo-M}R{2R,3R-cyclo-F}-NH2 were compared with that previously obtained for F{2S,3S-cyclo-M}RF-NH2 (J. Am. Chem. Sec. 1995, 117, 54). This approach facilitated comparisons between enantiomeric methanoamino acids (2S,3S-cyclo-M and 2R,3R-cyclo-M which have the amine and side chain functions trans-oriented across a cyclopropane) and between cis- and trans-2,3-methanoamino acids (i.e. 2R,3R-cyclo-M and 2R,3R-cyclo-F). To effect this comparison, the local influences of the 2,3-methanoamino acids were visualized and rationalized using phi,psi, dot plots and Newman projections, respectively. For 2S,3S-cyclo-M, the psi constraints caused by the 3-substituent were greater than the corresponding phi restrictions. The fundamental difference between the enantiomers of (E)-2,3-methanomethionine was that psi values for 2S,3S-cyclo-M in the peptidomimetics tended to be more positive than the corresponding torsions for 2R,3R-cyclo-M. For the cis methanolog, 2R,3R-cyclo-F, phi values were more severely affected than psi torsions, unlike the situation outlined for the E-cyclo-M enantiomers. NMR experiments also were performed to determine any conformational biases of F{2R,3R-cyclo-M}RF-NH2 and F{2S,3S-cyclo-M}R{2R,3R-cyclo-F}-NH2 in dimethyl sulfoxide (DMSO) solution. These data were then compared with results from the calculations. Both the NMR and QMD studies indicated that F{2S,3S-cyclo-M}R{2R,3R-cyclo-F}-NH2 had a bias toward a structure with all the side chains oriented on one face of the molecule and all the carbonyl vectors pointing in the opposite direction. Inconsistencies between the NMR and QMD data arose for F{2R,3R-cyclo-M}RF-NH2, i.e. conformers fitting the NMR data could be located in the families of structures generated by the QMD experiments, but they did not appear to be the mast favorable ones in the theoretical approach. It is suggested that these ambiguities could be due to contributions from different conformers with energies relatively close to the global minimum.

  DOI：

  10.1021/ja00118a017
• 作为产物：
  描述：

  (Z)-4-亚苄基-2-甲基噁唑-5(4h)-酮 在 盐酸 、 sodium hydroxide 、 乙酸酐 作用下， 以 水 、 溶剂黄146 、 丙酮 、 苯 为溶剂， 反应 163.0h， 生成 1-氨基-2-苯基环丙烷羧酸
  参考文献：
  名称：

  高度官能化的手性烯烃的非对映选择性环丙烷化反应合成不对称的1-氨基-2-苯基环丙烷羧酸

  摘要：

  同型手性苄基二烯酮基哌嗪和α-苯甲酰基氨基肉桂酸酯与重氮甲烷反应，可得到螺吡唑啉衍生物的非对映异构体比率高至良好，它们在进行光解和酸水解后所得到的螺环丙基化合物分别得到（+）-和（-）-1-氨基-2-苯环丙烷羧酸。

  DOI：

  10.1016/s0040-4039(00)99413-9

文献信息

• [EN] PEPTIDYL NITRILES AND USE THEREOF AS DIPEPTIDYL PEPTIDASE I INHIBITORS<br/>[FR] PEPTIDYL-NITRILES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE LA DIPEPTIDYLPEPTIDASE I
  申请人：ASTRAZENECA AB

  公开号：WO2009074829A1

  公开（公告）日：2009-06-18

  The present invention provides compounds of formula (I) in which n, y, X1, X2, A, B, R1, R2, R3, R4 and R5 are as defined in the specification, a process for their preparation, pharmaceutical compositions containing them and their use as dipeptidyl peptidase I (DPPI) inhibitors.

  本发明提供了式（I）中的化合物，其中n、y、X1、X2、A、B、R1、R2、R3、R4和R5如规范中定义，以及它们的制备方法、含有它们的药物组合物以及它们作为二肽基肽酶I（DPPI）抑制剂的用途。
• Novel Compounds 010
  申请人：Furber Mark

  公开号：US20090306042A1

  公开（公告）日：2009-12-10

  The present invention provides compounds of formula (I) in which n, y, X 1 , X 2 , A, B, R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the specification, a process for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了公式（I）中的化合物，其中n，y，X1，X2，A，B，R1，R2，R3，R4和R5如规范中所定义，以及它们的制备方法，含有它们的制药组合物以及它们在治疗中的应用。
• Catalytic Diastereo‐ and Enantioselective Cyclopropanation of <i>gem</i>‐Dihaloalkanes and Terminal Olefins
  作者：Hou‐Lu Liu、Xinyu Wang、Ke Gao、Zhaobin Wang

  DOI：10.1002/anie.202305987

  日期：2023.7.10

  We report the unprecedented chromium-catalyzed asymmetric cyclopropanation of readily available gem-dihaloalkanes and terminal olefins. Distinct from previous approaches, gem-dihaloalkanes serve as suitable precursors for non-stabilized carbenes or carbenoids, furnishing various functionalized chiral cyclopropanes. Mechanistic studies provide insights into the catalytic process, featuring radical-polar

  我们报道了前所未有的铬催化的现成宝石二卤代烷烃和末端烯烃的不对称环丙烷化反应。与以前的方法不同，偕二卤代烷烃可作为非稳定卡宾或类胡萝卜素的合适前体，提供各种官能化的手性环丙烷。机理研究提供了对以自由基-极性交叉为特征的催化过程的见解。
• Asymmetric syntheses of 1-amino-2-phenyl(alkyl)cyclopropanecarboxylic acids by diastereoselective cyclopropanation of highly functionalized monochiral olefines
  作者：Carmen Alcaraz、Ma Dolores Fernández、Ma Pilar de Frutos、Joseé L. Marco、Manuel Bernabé、Concepción Foces-Foces、Félix H. Cano

  DOI：10.1016/s0040-4020(01)89550-8

  日期：1994.1

  Monochiral alpha-benzamidocinnamic esters of N-methylephedrine or mandelic derivatives and benzylidene or alkylidene diketopiperazines, all obtained from oxazolones, react with diazomethane to give moderate to high diastereomeric excess (d.e) of pyrazoline derivatives which after photolysis and acid hydrolysis of the resulting cyclopropyl compounds, gave (1R,2R)-, (1S,2S)- or (1S,2R)-1-amino-2-phenyl(alkyl)cyclopropanecarboxylic acids. The enantiomerically pure dipeptide of the (1R,2R) enantiomer with S-proline was also obtained by selective cleavage of the diketopiperazine moiety. The structure of all compounds has been assessed by NMR studies and by X-ray crystallography analysis of an intermediate spiroderivative.
• US7902181B2
  申请人：——

  公开号：US7902181B2

  公开（公告）日：2011-03-08