(S)-3-benzamido-3-phenylpropanoic acid | 127413-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-benzamido-3-phenylpropanoic acid
• 英文别名: (S)-3-benzoylamino-3-phenyl-propionic acid；(S)-3-Benzoylamino-3-phenyl-propionsaeure；(3S)-3-benzamido-3-phenylpropanoic acid
• CAS: 127413-52-9
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: VRZBLYAGRWDUPY-AWEZNQCLSA-N

物化性质

• 熔点：
  225.0 °C
• 沸点：
  527.9±43.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-benzamido-3-phenylpropanoic acid 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Enantiopure 3-Amino-Substituted 1-Indanones, 1-Tetralones, and 1-Benzosuberones via Friedel–Crafts Cyclisation of ω-Aryl-β-benz­amido Acids

  摘要：

  Conjugate addition of enantiopure lithium (R)-N-benzyl-N-(-methylbenzyl)amide to a range of -aryl-,-unsaturated esters gives the corresponding -aryl--amino esters as single diastereoisomers in high yields. Friedel-Crafts cyclisation of the pendant carbonyl group onto the -aryl ring then gives a range of 3-amino-substituted 1-indanones, 1-tetralones, and 1-benzosuberones, representing an efficient and short protocol for the preparation of these benzo-fused carbocycles in enantiopure form.

  DOI：

  10.1055/s-0034-1380675
• 作为产物：
  描述：

  (3S)-3-氨基-3-苯基丙酸叔丁酯 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 (S)-3-benzamido-3-phenylpropanoic acid
  参考文献：
  名称：

  Enantiopure 3-Amino-Substituted 1-Indanones, 1-Tetralones, and 1-Benzosuberones via Friedel–Crafts Cyclisation of ω-Aryl-β-benz­amido Acids

  摘要：

  Conjugate addition of enantiopure lithium (R)-N-benzyl-N-(-methylbenzyl)amide to a range of -aryl-,-unsaturated esters gives the corresponding -aryl--amino esters as single diastereoisomers in high yields. Friedel-Crafts cyclisation of the pendant carbonyl group onto the -aryl ring then gives a range of 3-amino-substituted 1-indanones, 1-tetralones, and 1-benzosuberones, representing an efficient and short protocol for the preparation of these benzo-fused carbocycles in enantiopure form.

  DOI：

  10.1055/s-0034-1380675

文献信息

• Kinetic Resolution of Oxazinones: Rational Exploration of Chemical Space through the Design of Experiments
  作者：Polyssena Renzi、Christel Kronig、Armando Carlone、Serap Eröksüz、Albrecht Berkessel、Marco Bella

  DOI：10.1002/chem.201402380

  日期：2014.9.8

  The organocatalytic kinetic resolution of 4‐substituted oxazinones has been optimised (selectivity factor S up to 98, chiral oxazinone ee values up to 99.6 % (1 a–g) and product ee values up to 90 % (3 a–g)) in a rational way by applying the Design of Experiments (DoE) approach.

  对4-取代的恶嗪酮的有机催化动力学拆分进行了优化（选择性因子S最高为98，手性恶嗪酮ee值最高为99.6％（1 a – g），产物ee值最高为90％（3 a – g））。通过应用实验设计（DoE）方法的一种合理方法。
• A Reinvestigation of the Role of the Sorbic Acid Tail on the Antibacterial and Anti‐Tuberculosis Properties of Moiramide B
  作者：Irina Kollmorgen、Nathalie Bachmann、Michael Dal Molin、Carsten Degenhart、Eldar Zent、Vikram Pareek、Uwe Koch、Jan Rybniker、Nils Metzler-Nolte、Raphael Stoll、Bert Klebl、Julia Elisabeth Bandow、Jürgen Scherkenbeck

  DOI：10.1002/cmdc.202200631

  日期：——

  New subpocket: In this study we demonstrate that the sorbic acid tail of the pseudopeptide moiramide B is essential for acetyl-CoA carboxylase binding. Based on structure–activity and molecular modeling data, a binding model was developed for N-terminally modified moiramide derivatives.

  新子口袋：在这项研究中，我们证明了假肽 moiramide B 的山梨酸尾部对于乙酰辅酶 A 羧化酶结合是必不可少的。基于结构-活性和分子建模数据，为 N-末端修饰的莫拉酰胺衍生物开发了结合模型。
• Stereochemistry and Mechanism of a Microbial Phenylalanine Aminomutase
  作者：Nishanka Dilini Ratnayake、Udayanga Wanninayake、James H. Geiger、Kevin D. Walker

  DOI：10.1021/ja2030728

  日期：2011.6.8

  The stereochemistry of a phenylalanine aminomutase (PAM) on the andrimid biosynthetic pathway in Pantoea agglomerans (Pa) is reported. PaPAM is a member of the 4-methylidene-1H-imidazol-5(4H)-one (MIO)-dependent family of catalysts and isomerizes (2S)-alpha-phenylalanine to (3S)-beta-phenylalanine, which is the enantiomer of the product made by the mechanistically similar aminomutase TcPAM from Taxus plants. The NH2 and pro-(3S) hydrogen groups at C-alpha and C-beta, respectively, of the substrate are removed and interchanged completely intramolecularly with inversion of configuration at the migration centers to form P-phenylalanine. This is a contrast to the retention of configuration mechanism followed by TcPAM.
• Pulmonary cryptococcosis and Capillaria aerophila infection in an FIV-positive cat
  作者：VR BARRS、P. MARTIN、RG NICOLL、JA BEATTY、R. MALIK

  DOI：10.1111/j.1751-0813.2000.tb10581.x

  日期：2000.3

  A 12‐year‐old, FIV‐positive, domestic longhair cat was presented with a history of sneezing and coughing during the previous seven months. On thoracic radiographs, a prominent bronchial pattern and three focal, opacified nodules were seen. Cytology of bronchoalveolar lavage fluid demonstrated spherical, capsulate, narrow‐necked, budding yeasts within macrophages. Culture of the fluid yielded a heavy growth of Cryptococcus neoformans var neoformans. The serum latex cryptococcal antigen agglutination test titre was 158. The cat was treated with itraconazole and the cough resolved over a 5‐month period but then recurred. Repeat thoracic radiographs showed resolution of the pulmonary nodules but a persistent bronchial pattern. Adult nematodes and ova with morphology characteristic of Capillaria aerophila were seen in bronchoalveolar lavage fluid and no yeasts were cultured from the fluid. The cryptococcal titre was zero. The lungworm infection was treated successfully with abamectin and the cough resolved. Immunosuppression related to FIV infection may have predisposed this cat to sequential respiratory tract infections.
• Asymmetric synthesis of α- and β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines
  作者：Raquel Almansa、Juan F. Collados、David Guijarro、Miguel Yus

  DOI：10.1016/j.tetasy.2010.03.046

  日期：2010.6

  The diastereoselective addition of triorganozincates to (R)-N-(tert-butanesulfinyl)imines has been used as a key step to achieve the synthesis of highly enantiomerically enriched N-protected alpha- and beta-amino acids. Desulfinylation of the addition products followed by benzoylation of the nitrogen atom of the obtained primary amines and oxidation of one of the substituents on the carbon atom connected to the nitrogen complete the sequence. Using the same configuration in the sulfinyl chiral auxiliary, alpha-amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. alpha,alpha-Disubstituted alpha-amino esters with high enantiomeric purity can also be prepared when a-imino esters are the starting substrates. (C) 2010 Elsevier Ltd. All rights reserved.