甲基(1R,2R)-1-氨基-2-苯基环丙烷羧酸酯 | 123806-63-3

• 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: 甲基(1R,2R)-1-氨基-2-苯基环丙烷羧酸酯
• 中文别名: (8S,9S,10R,13S,14S,17S)-17-[(1R)-1-羟基丙-2-炔-1-基]-10,13-二甲基-1,2,6,7,8,9,10,11,12,13,14,15,16,17-十四氢-3H-环戊二烯并[a]菲-3-酮(non-preferredname)
• 英文名称: methyl (1R,2S)-1-amino-2-phenylcyclopropanecarboxylate
• 英文别名: methyl (1R,2S)-1-amino-2-phenylcyclopropane-1-carboxylate
• CAS: 123806-63-3
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: SSNHIYGBNLNDBQ-GXSJLCMTSA-N

物化性质

• 沸点：
  279.9±40.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基(1R,2R)-1-氨基-2-苯基环丙烷羧酸酯 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.75h， 生成
  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：

  methyl (1R,2S)-1-nitro-2-phenylcyclopropanecarboxylate 在 盐酸 、 锌 作用下， 以 异丙醇 为溶剂， 反应 2.0h， 生成 甲基(1R,2R)-1-氨基-2-苯基环丙烷羧酸酯
  参考文献：
  名称：

  使用由硝基乙酸甲酯衍生的叶立德碘鎓通过烯烃的催化不对称环丙烷化反应快速合成环丙烷 α-氨基酸

  摘要：

  据报道，使用由碘代苯和硝基乙酸甲酯原位生成的苯基碘鎓叶立德，对烯烃进行了高度对映选择性（高达 97.5% ee）和非对映选择性（95:5 dr 反式/顺式）Cu（I）催化的烯烃环丙烷化反应。环丙烷化反应对多种烯烃具有高对映选择性，反应在室温下进行。1-硝基环丙基酯是通用的结构单元，可分别通过两步和三步从市售产品中获得相应的环丙烷氨基酯和氨基环丙烷。

  DOI：

  10.1021/ja056192l

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...
• Catalytic asymmetric synthesis of nitrocyclopropane carboxylates
  作者：Benoît Moreau、Dino Alberico、Vincent N.G. Lindsay、André B. Charette

  DOI：10.1016/j.tet.2011.05.113

  日期：2012.4

  A Cu(I)-catalyzed asymmetric cyclopropanation of alkenes with an iodonium ylide has been developed. The copper source, hypervalent iodine source, solvent, and additives all have a significant effect on the yields and enantioselectivities. High enantioselectivity (up to 99:1 er) and diastereoselectivity (95:5 dr trans/cis) were achieved for a wide range of alkenes. Conditions were developed to convert

  已经开发了具有碘鎓内鎓盐的Cu（I）催化的烯烃的不对称环丙烷化反应。铜源，高价碘源，溶剂和添加剂都对产率和对映选择性有重要影响。对于多种烯烃，均实现了高对映选择性（高达99：1 er）和非对映选择性（95：5 dr反式/顺式）。研究了将反式产物转化为顺式异构体的条件。另外，将1-硝基环丙基羧酸盐转化成相应的取代的环丙烷氨基酸和氨基环丙烷。此外，还记录了这些化合物中Zn介导的In和In介导的硝基还原反应之间关于腐蚀的比较研究。
• MAPELLI, CLAUDIO;STAMMER, CHARLES H.;LOK, STAN;MIERKE, DALE F.;GOODMAN, M+, INT. J. PEPTIDE AND PROTEIN RES., 32,(1988) N, C. 484-495
  作者：MAPELLI, CLAUDIO、STAMMER, CHARLES H.、LOK, STAN、MIERKE, DALE F.、GOODMAN, M+

  DOI：——

  日期：——
• 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.
• Expedient Synthesis of Cyclopropane α-Amino Acids by the Catalytic Asymmetric Cyclopropanation of Alkenes Using Iodonium Ylides Derived from Methyl Nitroacetate
  作者：Benoît Moreau、André B. Charette

  DOI：10.1021/ja056192l

  日期：2005.12.1

  A highly enantioselective (up to 97.5% ee) and diastereoselective (95:5 dr trans/cis) Cu(I)-catalyzed cyclopropanation of alkenes using phenyliodonium ylide generated in situ from iodosobenzene and methyl nitroacetate is reported. The cyclopropanation took place with high enantioselectivity for a wide range of alkenes, and the reaction was performed at room temperature. 1-Nitrocyclopropyl esters are

  据报道，使用由碘代苯和硝基乙酸甲酯原位生成的苯基碘鎓叶立德，对烯烃进行了高度对映选择性（高达 97.5% ee）和非对映选择性（95:5 dr 反式/顺式）Cu（I）催化的烯烃环丙烷化反应。环丙烷化反应对多种烯烃具有高对映选择性，反应在室温下进行。1-硝基环丙基酯是通用的结构单元，可分别通过两步和三步从市售产品中获得相应的环丙烷氨基酯和氨基环丙烷。