(S)-tert-butyl (2-oxo-1-phenyl-2-(phenylamino)ethyl)carbamate | 329791-72-2

• 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: (S)-tert-butyl (2-oxo-1-phenyl-2-(phenylamino)ethyl)carbamate
• 英文别名: tert-butyl N-[(1S)-2-anilino-2-oxo-1-phenylethyl]carbamate
• CAS: 329791-72-2
• 化学式: C₁₉H₂₂N₂O₃
• 分子量: 326.395
• InChiKey: BHCHSFPFLROJTD-INIZCTEOSA-N

物化性质

• 沸点：
  540.2±50.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl (2-oxo-1-phenyl-2-(phenylamino)ethyl)carbamate 在 lithium aluminium tetrahydride 、 三乙胺 、 三氯化磷 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 8.58h， 生成 (4S)-2-chloro-3-methyl-1,4-diphenyl-1,3,2-diazaphospholidine
  参考文献：
  名称：

  Development of P∗-monodentate diamidophosphites with a C1-symmetric 1,2-diamine backbone: the effects of substituents in the 1,3,2-diazaphospholidine cycle on Pd-catalyzed asymmetric allylations

  摘要：

  We have designed and synthesized a small library of modular monodentate diamidophosphite ligands with stereogenic phosphorus atoms. The library was prepared efficiently from the commercially available and inexpensive (S)-N-Boc-amino acids. These novel ligands were screened in the Pd-catalyzed asymmetric allylations of (E)-1,3-diphenylallyl acetate with dimethyl malonate as the C-nucleophile with up to 93% ee being obtained. The results showed that the different substituents in the 1,3,2-diazaphospholidine cycle had remarkable effects on the enantioselectivity. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.010
• 作为产物：
  描述：

  L-苯甘氨酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 8.33h， 生成 (S)-tert-butyl (2-oxo-1-phenyl-2-(phenylamino)ethyl)carbamate
  参考文献：
  名称：

  具有含L-苯甘氨酸的分支帽的PXD101类似物作为组蛋白脱乙酰基酶抑制剂

  摘要：

  组蛋白脱乙酰基酶（HDAC）允许组蛋白更紧密地包裹DNA，并最终导致某些肿瘤抑制基因的抑制。组蛋白脱乙酰基酶抑制剂（HDACIs）已被证明对肿瘤发生和肿瘤进展有影响。在这项研究中，我们报道了具有L-苯基甘氨酸帽的HDACIs的新型PXD101类似物的设计，合成和体外活性评估。我们的结果表明，HDACs对化合物10k，10r和10s的抑制活性不仅优于首个批准的HDACI SAHA，而且与其母体化合物PXD101（2014年最近批准的HDACI）相当。但是，所有6个选定的PXD101类似物均表现出适度的体外抗增殖活性，效果不如PXD101和SAHA。代表性化合物10s具有与PXD101相似的HDAC同工型选择性图谱，这表明引入含L-苯基甘氨酸的支链帽基团不会显着改变PXD101的同工型选择性。

  DOI：

  10.1111/cbdd.12787

文献信息

• Amine Activation:<i>N</i>-Arylamino Acid Amide Synthesis from Isothioureas and Amino Acids
  作者：Yan-Ping Zhu、Pieter Mampuys、Sergey Sergeyev、Steven Ballet、Bert U. W. Maes

  DOI：10.1002/adsc.201700134

  日期：2017.7.17

  functional group compatibility, with respect to side chain functionality of the amino acid (e. g. aliphatic and aromatic OH, (hetero)aromatic NH, amide NH, thioether), and the chiral amino acids do not undergo epimerization. The mechanism of the new amide synthesis has been studied.

  Ñ -arylamino酰胺已经通过基于新方法被合成ñ -芳基胺活化成异硫脲，随后用下铁催化氨基酸反应。可以使用三组分反应与市售试剂叔丁基异氰化物和S-苯基苯硫代磺酸盐轻松地制备活化的N-芳基胺。相对于氨基酸（例如脂族和芳族OH，（杂）芳族NH，酰胺NH，硫醚）的侧链官能度，该方案显示出广泛的官能团相容性，并且手性氨基酸不发生差向异构化。已经研究了新酰胺合成的机理。
• Design, synthesis, and insecticidal activities of novel diamide derivatives with alpha‐amino acid subunits
  作者：Rui‐Jia Chen、Jun‐Jie Wang、Li Han、Yu‐Cheng Gu、Zhi‐Ping Xu、Jia‐Gao Cheng、Xu‐Sheng Shao、Xiao‐Yong Xu、Zhong Li

  DOI：10.1002/jhet.4268

  日期：2021.7

  A series of diamide derivatives containing α-amino acids were designed and synthesized. These compounds were evaluated for their insecticidal activities against Plutella xylostella, Mythimna separate, Myzus persicae, and Tetranychus cinnabarinus. Most of the title compounds containing an l-phenylglycine skeleton were endowed with good activities at the concentration of 500 mg·L−1. Compounds (R)-A6

  设计并合成了一系列含有α-氨基酸的二酰胺衍生物。评估了这些化合物对小菜蛾、单独的 Mythimna、桃蚜和红叶螨的杀虫活性。大多数含有l-苯基甘氨酸骨架的标题化合物在500 mg·L -1的浓度下具有良好的活性。化合物( R)-A6显示出作为杀虫先导物的进一步优化的潜在价值，LC 50值为86.8 mg·L -1。
• 一种含有苯甘氨酸的肉桂酰胺类组蛋白去乙酰化酶抑制剂及其制备方法和应用
  申请人：山东大学

  公开号：CN105481736A

  公开（公告）日：2016-04-13

  本发明涉及一种含有苯甘氨酸的肉桂酰胺类组蛋白去乙酰化酶抑制剂及其制备方法和应用。所述化合物具有式I的结构。本发明还涉及含有式I结构化合物的药物组合物。本发明的化合物，用于制备预防或治疗与组蛋白去乙酰化酶活性异常表达相关的哺乳动物疾病的药物。
• Proline-based dipeptides with two amide units as organocatalyst for the asymmetric aldol reaction of cyclohexanone with aldehydes
  作者：Fubin Chen、Shi Huang、Hui Zhang、Fengying Liu、Yungui Peng

  DOI：10.1016/j.tet.2008.07.051

  日期：2008.9

  A series of proline-based dipeptide organocatalysts with two amide units (1-16) have been developed and evaluated in the direct catalytic asymmetric aldol reactions of aldehydes with cyclohexanone. These catalysts showed good solubility in organic solvents compared with their corresponding carboxyl terminal dipeptides. The robust amide bond formation allowed structural modifications and fine tuning of catalyst properties by varying the stereo and electronic effects of the terminal amide to affect the ability of hydrogen bonding formation between the catalysts and the substrates. The reactions proceeded smoothly in high yields (up to 99%), enantioselectivities (up to 98% ee) and anti-diastereoselectivities (up to 99:1) in the presence of bifunctional organocatalyst 4 under the optimal reaction conditions. (C) 2008 Elsevier Ltd, All rights reserved.
• MPAI-Ligand Accelerated Pd-Catalyzed C(<i>sp</i>³)–H Arylation of Free Aliphatic Acids
  作者：Zi-Yu Dong、Jia-Hui Zhao、Peng Wang、Jin-Quan Yu

  DOI：10.1021/acs.orglett.2c02933

  日期：2022.10.28