2-amine-N-[(S)-α-phenylethyl]benzamide | 783371-72-2

• 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: 2-amine-N-[(S)-α-phenylethyl]benzamide
• 英文别名: 2-amino-N-[(S)-α-methylbenzyl]-benzamide；(S)-2-amino-N-(1-phenylethyl)benzamide；2-amino-N-[(1S)-1-phenylethyl]benzamide
• CAS: 783371-72-2
• 化学式: C₁₅H₁₆N₂O
• mdl: MFCD19538521
• 分子量: 240.305
• InChiKey: KBRHMOXICLSVTL-NSHDSACASA-N

物化性质

• 熔点：
  136-138 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  453.5±38.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amine-N-[(S)-α-phenylethyl]benzamide 在 platinum(IV) oxide 盐酸 、 硫酸 、 氢气 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 20.0~115.0 ℃ 、413.68 kPa 条件下， 反应 8.5h， 生成 (1R,2R)-2-氨基环己甲酸
  参考文献：
  名称：

  Synthesis of enantiopure cis- and trans-2-aminocyclohexane-1-carboxylic acids from octahydroquinazolin-4-ones

  摘要：

  The chemoselective and diastereoselective hydrogenation of 2,3-dibydro-3-[(S)-alpha-methylbenzyl]-4-quinazolinone 2 affords octahydroquinazolinones cis-3 and cis-4. Epimerization of cis-3 and cis-4 using t-BuO-K+ produces trans-5 and trans-6, respectively. Hydrolysis with HCl of these octahydroquinazolinones leads to the free, enantiomerically pure, cis- and trans-2-aminocyclohexane-1-carboxylic acids 7-10. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.08.032
• 作为产物：
  描述：

  N-<(S)-1-phenylethyl>-2-nitrobenzamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 2-amine-N-[(S)-α-phenylethyl]benzamide
  参考文献：
  名称：

  Synthesis and structure of chiral 2,6-bis[(2-carbamoylphenyl)carbamoyl]pyridine ligands

  摘要：

  The synthesis and structure of a series of enantiomerically pure 2,6-bis[(2-carbamoylphenyl)carbamoyl]-pyridine ligands (H(2)a-c) are described. Appended from the aryl groups are optically active groups which provide a chiral environment around the planar pyridine core. NMR and X-ray diffraction studies show that these ligands contain helical character which is maintained by a network of intramolecular hydrogen bonds. These ligands can bind metal ions through their tridentate diamidato-pyridyl chelate to form optically active metal complexes. The modular design of these ligands offers a variety of chiral environments about the metal chelate that can be useful in the synthesis of metal reagents for asymmetric transformations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01486-5

文献信息

• Sirtuin Inhibiting Compounds
  申请人：Sinclair David A

  公开号：US20090137681A1

  公开（公告）日：2009-05-28

  Provided herein are compositions and methods for treating or preventing cancer and autoimmune diseases. Compositions comprise a sirtuin inhibitory compound that decreases the activity of a sirtuin, such as SIRT1 or Sir2. Exemplary methods comprise contacting a cell or a molecule with a sirtuin inhibitory compound that decreases the activity of a sirtuin and thereby reduces the life span of a cell, kills the cell or renders it susceptible to certain cell stresses including radiation and chemotherapy. Other methods include treating pathogens expressing a sirtuin.

  本文提供了治疗或预防癌症和自身免疫疾病的组合物和方法。组合物包括抑制sirtuin的化合物，降低sirtuin的活性，如SIRT1或Sir2。示例方法包括将细胞或分子与抑制sirtuin的化合物接触，降低sirtuin的活性，从而缩短细胞的寿命，杀死细胞或使其对包括放射治疗和化疗在内的某些细胞应激变得敏感。其他方法包括治疗表达sirtuin的病原体。
• Reaction of 2-Aminobenzamides with Indoline-2,3-Dione in an Ionic Liquid in the Presence and Absence of Iodine
  作者：Jie Sheng、Ke Yang、Mei-Mei Zhang、Xiang-Shan Wang

  DOI：10.3184/174751912x13303708813998

  日期：2012.3

  The reaction of 2-aminobenzamides with indoline-2,3-dione in ionic liquids, selectively gives 1’,3'-dihydrospiro[indolin-2-one-3,2'-quinazolin]-4'-ones in the presence of 5 mol% iodine, while giving 2-(1-acetyl-3-hydroxy-2-oxoindolin-3-ylamino) benzamide derivatives in the absence of iodine. Quinazolinones have great physiological significance and pharmaceutical uses.

  2-aminobenzamides 与吲哚啉-2,3-二酮在离子液体中反应，在 5 摩尔碘存在下可选择性地生成 1',3'-二氢螺[吲哚啉-2-酮-3,2'-喹唑啉]-4'-酮，而在无碘存在下则生成 2-(1-乙酰基-3-羟基-2-氧代吲哚啉-3-基氨基)苯甲酰胺衍生物。喹唑啉酮类化合物具有重要的生理意义和医药用途。
• A novel approach for the synthesis of functionalized hydroxylamino derivative of dihydroquinazolinones
  作者：Chikkanti Jaganmohan、Vinay Kumar K. P.、Venkateshwarlu R.、Sandeep Mohanty、Jaydeep Kumar、Venkateswara Rao B.、Akula Raghunadh、Krishnaji Tadiparthi

  DOI：10.1080/00397911.2020.1768406

  日期：2020.7.17

  Abstract A new metal-free and modular approach for the synthesis of various functionalized dihydroquinazolinones has been developed from isatoic anhydride, amines, 4-chloro-N-hydroxybenzimidoylchloride to yield up to 71%. The reaction has been screened in various bases, solvents at different temperatures. The substrate scope of the reaction has been studied with various amines and the possible reaction

  摘要 一种新的无金属和模块化方法用于合成各种功能化二氢喹唑啉酮类化合物，从靛红酸酐、胺类、4-氯-N-羟基苯并亚氨基酰氯的收率高达 71%。该反应已在各种碱、不同温度下的溶剂中进行筛选。对各种胺类反应的底物范围进行了研究，并提出了该反应可能的反应机理。图形概要
• Base mediated spirocyclization of quinazoline: one-step synthesis of spiro-isoindolinone dihydroquinazolinones
  作者：Rapolu Venkateshwarlu、V. Narayana Murthy、Krishnaji Tadiparthi、Satish P. Nikumbh、Rajesh Jinkala、Vidavalur Siddaiah、M. V. Madhu babu、Hindupur Rama Mohan、Akula Raghunadh

  DOI：10.1039/c9ra09567e

  日期：——

  A novel approach for the spiro-isoindolinone dihydroquinazolinones has been demonstrated from 2-aminobenzamide and 2-cyanomethyl benzoate in the presence of KHMDS as a base to get moderate yields.

  已经展示了一种新颖的方法，通过在KHMDS存在下，从2-氨基苯甲酰胺和2-氰甲基苯甲酸酯中得到螺环异吲哚酮二氢喹唑啉酮，以获得中等产率。
• Synthesis of 2,3-Dihydro-4(1H)- quinazolinones
  作者：Jaime Escalante、Patricia Flores、Jaime M. Priego

  DOI：10.3987/com-04-10130

  日期：——

  An improved procedure for the synthesis of 2-substituted 2,3-dihydro-4(1H)-quinazolinones through diastereomer separation of the corresponding quinazolinones derivatives is presented. The determination of their absolute configurations was obtained by X-Ray diffraction.

  提出了一种通过对相应的喹唑啉酮衍生物进行非对映异构体分离来合成 2-取代的 2,3-二氢-4(1H)-喹唑啉酮的改进方法。它们的绝对构型的确定是通过 X 射线衍射获得的。