1-氨基-2-苯基环丙烷羧酸 | 3200-80-4

• 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: (Z)-1-amino-2-phenylcyclopropanecarboxylic acid
• 英文别名: cis-1-amino-2-phenylcyclopropanecarboxylic acid；(1S,2S)-1-amino-2-phenylcyclopropane-1-carboxylic acid
• CAS: 3200-80-4；3200-83-7；63140-93-2；82112-08-1；91327-47-8；91327-48-9；123039-87-2；129101-41-3；129101-43-5
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: MRUPFDZGTJQLCH-WPRPVWTQSA-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：

  1-氨基-2-苯基环丙烷羧酸 在 sodium carbonate 作用下， 以 乙醚 为溶剂， 生成 methyl 1-benzamido-2-phenyl-cyclopropanecarboxylate
  参考文献：
  名称：

  Bernabe; Cuevas; Fernandez-AlvarezE., European Journal of Medicinal Chemistry, 1979, vol. 14, # 1, p. 33 - 45

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 1-benzamido-2-phenyl-cyclopropanecarboxylate 在 氢氧化钾 、 sodium hydride 作用下， 反应 93.0h， 生成 1-氨基-2-苯基环丙烷羧酸
  参考文献：
  名称：

  Arenal, I.; Bernabe, M.; Alvarez, E. Fernandez, Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 607 - 614

  摘要：

  DOI：

文献信息

• New α,β-didehydroamino acid derivatives as precursors in the synthesis of 1-aminocyclopropanecarboxylic acids
  作者：Carlos Cativiela、María D. Díaz-de-Villegas、Ana I. Jiménez

  DOI：10.1016/s0040-4020(01)85381-3

  日期：1994.1

  idehydroalanine methyl ester with diazoalkanes or ylides gives the corresponding cyclopropane derivatives in high yields. The cis/trans ratio of these compounds was dependent on substrate, reagent and reaction temperature. From stereochemically homogeneous compounds the corresponding 1-aminocyclopropanecarboxylic acids were easily obtained by acid hydrolysis.

  N-（二苯基亚甲基）二氢化氢丙氨酸甲酯和N- [双（甲硫基亚甲基）二氢化氢丙氨酸甲酯与重氮烷烃或碘化物的反应以高收率得到相应的环丙烷衍生物。这些化合物的顺/反比取决于底物，试剂和反应温度。从立体化学均相化合物中，通过酸水解容易地获得相应的1-氨基环丙烷羧酸。
• Synthesis of asymmetric 1-amino-2-phenylcyclopropanecarboxylic acids by diastereoselective cyclopropanation of highly functionalized homochiral olefines
  作者：Ma Dolores Fernández、Ma Pilar de Frutos、José L. Marco、Eldiberto Fernández-Alvarez、Manuel Bernabé

  DOI：10.1016/s0040-4039(00)99413-9

  日期：1989.1

  Homochiral benzylidenediketopiperazine and α-benzoylaminocinnamic esters react with diazomethane giving high to good diastereomeric ratios of spiropyrazoline derivatives which, on photolysis and acid hydrolysis of the resulting spirocyclopropyl compounds gave, respectively, (+)- and (−)-1-amino-2-phenylcyclopropanecarboxylic acids.

  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。
• Tricyclic compounds protein kinase inhibitors for enhancing the efficacy of anti-neoplastic agents and radiation therapy
  申请人：Benedict Suzanne

  公开号：US20060004052A1

  公开（公告）日：2006-01-05

  Protein kinase, such as CHK-1, inhibiting tricyclic compounds of the following formula (wherein R 2 , R 3 and R 4 are as defined in the specification) pharmaceutical compositions containing effective amounts of said compounds or their salts are useful as a single agent or in combination with an anti-neoplastic agent or therapeutic radiation having an anti-neoplastic effect for treating diseases or conditions such as cancers.

  蛋白激酶（例如CHK-1）抑制下列式子中三环化合物（其中R2，R3和R4如规范中定义）的药物组合物（或其盐）在单独使用或与具有抗肿瘤作用的抗肿瘤剂或治疗性放射线组合使用时，可用于治疗癌症等疾病或病况。
• TRICYCLIC COMPOUNDS PROTEIN KINASE INHIBITORS FOR ENHANCING THE EFFICACY OF ANTI-NEOPLASTIC AGENTS AND RADIATION THERAPY
  申请人：Benedict Suzanne

  公开号：US20070135415A1

  公开（公告）日：2007-06-14

  Protein kinase, such as CHK-1, inhibiting tricyclic compounds of the following formula (wherein R 2 , R 3 and R 4 are as defined in the specification) pharmaceutical compositions containing effective amounts of said compounds or their salts are useful as a single agent or in combination with an anti-neoplastic agent or therapeutic radiation having an anti-neoplastic effect for treating diseases or conditions such as cancers. The current invention relates to the making and using of such compounds.

  蛋白激酶，例如CHK-1，抑制以下式子中三环化合物（其中R2，R3和R4如规范所定义）的制剂（或其盐）的有效量的制药组合物，可用作单一剂量或与抗肿瘤剂或具有抗肿瘤作用的治疗性放射线组合使用，用于治疗癌症等疾病或病情。本发明涉及制备和使用这种化合物。
• 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。