methyl (1RS,2RS)-1-[(tert-butoxycarbonyl)amino]-2-phenyl-1-cyclopropanecarboxylate

• 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: methyl (1RS,2RS)-1-[(tert-butoxycarbonyl)amino]-2-phenyl-1-cyclopropanecarboxylate
• 英文别名: methyl (1S,2S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylcyclopropane-1-carboxylate
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: AWAKPKGIPXODOP-LRDDRELGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1RS,2RS)-1-[(tert-butoxycarbonyl)amino]-2-phenyl-1-cyclopropanecarboxylate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以100%的产率得到(1R,2R)-1-methoxycarbonyl-2-phenylcyclopropanaminium chloride
  参考文献：
  名称：

  A formyl peptide substituted with a conformationally constrained phenylalanine residue evokes a selective immune response in human neutrophils

  摘要：

  Formyl-Met-Leu-Phe-OH (fMLP) binds to formyl peptide receptors, FPR1 and FPR2, and evokes migration and superoxide anion production in human neutrophils. To obtain a more effective and selective ligand, fMLP analogs in which the Phe residue was substituted with four isomers of cyclopropanephenylalanine were synthesized. While Z-isomer peptides induced both migration and superoxide anion production, E-isomer peptides elicited only chemotaxis. Homologous receptor desensitization experiments revealed that E-isomer peptides bound to FPR2. Although a selective agonist of chemotaxis also binds to FPR2 without increasing intracellular calcium concentration, E-isomer peptide elevated the concentration to the same level as fMLP. Understanding of mechanisms responsible for the selectivity of the reported selective agonists and rPhe-substituted analogs should prove useful for revealing the relationship between receptor-ligand interactions and biological responses of human neutrophils. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.046
• 作为产物：
  描述：

  diethyl 2-phenylcyclopropane-1,1-dicarboxylate 在 硫酸 、 sodium hydroxide 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 43.0h， 生成 methyl (1RS,2RS)-1-[(tert-butoxycarbonyl)amino]-2-phenyl-1-cyclopropanecarboxylate
  参考文献：
  名称：

  A formyl peptide substituted with a conformationally constrained phenylalanine residue evokes a selective immune response in human neutrophils

  摘要：

  Formyl-Met-Leu-Phe-OH (fMLP) binds to formyl peptide receptors, FPR1 and FPR2, and evokes migration and superoxide anion production in human neutrophils. To obtain a more effective and selective ligand, fMLP analogs in which the Phe residue was substituted with four isomers of cyclopropanephenylalanine were synthesized. While Z-isomer peptides induced both migration and superoxide anion production, E-isomer peptides elicited only chemotaxis. Homologous receptor desensitization experiments revealed that E-isomer peptides bound to FPR2. Although a selective agonist of chemotaxis also binds to FPR2 without increasing intracellular calcium concentration, E-isomer peptide elevated the concentration to the same level as fMLP. Understanding of mechanisms responsible for the selectivity of the reported selective agonists and rPhe-substituted analogs should prove useful for revealing the relationship between receptor-ligand interactions and biological responses of human neutrophils. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.046

文献信息

• Asymmetric Cyclopropanations by Rhodium(II) <i>N</i>-(Arylsulfonyl)prolinate Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Alkenes. Practical Enantioselective Synthesis of the Four Stereoisomers of 2-Phenylcyclopropan-1-amino Acid
  作者：Huw M. L. Davies、Paul R. Bruzinski、Debra H. Lake、Norman Kong、Michael J. Fall

  DOI：10.1021/ja9604931

  日期：1996.1.1

  to]dirhodium. The carbenoid structure has a critical effect on the degree of asymmetric induction, and the combination of a small electron-withdrawing group such as a methyl ester and an electron-donating group such as vinyl or phenyl resulted in the highest levels of enantioselectivity. The use of electron neutral alkenes and pentane as solvent also enhanced the enantioselectivity of the process.

  N-(芳基磺酰基)脯氨酸铑在烯烃存在下催化乙烯基重氮甲烷的分解导致以高度非对映选择性和对映选择性模式合成官能化环丙烷的非常通用的方法。进行了详细研究以确定控制该过程的对映选择性的关键因素。使用环状 N-(芳基磺酰基)氨基酸作为二铑催化剂的配体获得了最高水平的对映选择性，优化的催化剂是四[N-[(4-十二烷基苯基)磺酰基]-(L)-脯氨酰]二铑。卡宾结构对不对称诱导的程度有关键影响，小的吸电子基团（例如甲酯）和给电子基团（例如乙烯基或苯基）的组合导致最高水平的对映选择性。使用电子中性烯烃和戊烷作为溶剂也提高了该过程的对映选择性。这种化学的合成效用...
• Diastereoselective Synthesis of Cyclopropane Amino Acids Using Diazo Compounds Generated in Situ
  作者：Luke A. Adams、Varinder K. Aggarwal、Roger V. Bonnert、Bettina Bressel、Russell J. Cox、Jon Shepherd、Javier de Vicente、Magnus Walter、William G. Whittingham、Caroline L. Winn

  DOI：10.1021/jo035060c

  日期：2003.11.1

  E selectivity, while reactions in the presence of meso-tetraphenylporphyrin iron chloride gave predominantly the corresponding Z isomers. The synthetic utility of this process was demonstrated in the synthesis of (+/-)-(Z)-2,3-methanophenylalanine [(+/-)-(Z)-1], the anti-Parkinson (+/-)-(E)-2,3-methano-m-tyrosine [(+/-)-(E)-2], and the natural product (+/-)-coronamic acid [(+/-)-3].

  描述了一种简单且高产率的制备环丙烷氨基酸的方法。该新方法涉及使用从相应的甲苯磺酰salts盐就地产生的芳基和不饱和重氮化合物对易得的脱氢氨基酸进行一锅环丙烷化。发现热的1，3-偶极环加成反应，接着进行氮挤出，得到具有良好E选择性的环丙烷氨基酸衍生物，而在中四苯基卟啉氯化铁存在下的反应主要产生了相应的Z异构体。在合成（+/-）-（Z）-2,3-methanophenylphenylineine [（+/-）-（Z）-1]，抗帕金森氏菌（+/-）中证明了该方法的合成效用-（E）-2，3-甲基-间-酪氨酸[（+/-）-（E）-2]和天然产物（+/-）-冠状酸[（+/-）-3]。
• A formyl peptide substituted with a conformationally constrained phenylalanine residue evokes a selective immune response in human neutrophils
  作者：Ryo Hayashi、Masaya Miyazaki、Satoshi Osada、Hiroshi Kawasaki、Ichiro Fujita、Yuhei Hamasaki、Hiroaki Kodama

  DOI：10.1016/j.bmc.2012.11.046

  日期：2013.2

  Formyl-Met-Leu-Phe-OH (fMLP) binds to formyl peptide receptors, FPR1 and FPR2, and evokes migration and superoxide anion production in human neutrophils. To obtain a more effective and selective ligand, fMLP analogs in which the Phe residue was substituted with four isomers of cyclopropanephenylalanine were synthesized. While Z-isomer peptides induced both migration and superoxide anion production, E-isomer peptides elicited only chemotaxis. Homologous receptor desensitization experiments revealed that E-isomer peptides bound to FPR2. Although a selective agonist of chemotaxis also binds to FPR2 without increasing intracellular calcium concentration, E-isomer peptide elevated the concentration to the same level as fMLP. Understanding of mechanisms responsible for the selectivity of the reported selective agonists and rPhe-substituted analogs should prove useful for revealing the relationship between receptor-ligand interactions and biological responses of human neutrophils. (C) 2012 Elsevier Ltd. All rights reserved.