N-benzyloxycarbonyl-(S)-phenylalanine piperidine amide | 15368-74-8

• 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: N-benzyloxycarbonyl-(S)-phenylalanine piperidine amide
• 英文别名: (S)-N-(benzyloxycarbonyl)phenylalanine piperidylamide；(S)-benzyl (1-oxo-3-phenyl-1-(piperidin-1-yl)propan-2-yl)carbamate；Cbz-L-Phe-piperidyl；Phenylmethyl N-[(1S)-2-oxo-1-(phenylmethyl)-2-(1-piperidinyl)ethyl]carbamate；benzyl N-[(2S)-1-oxo-3-phenyl-1-piperidin-1-ylpropan-2-yl]carbamate
• CAS: 15368-74-8
• 化学式: C₂₂H₂₆N₂O₃
• 分子量: 366.46
• InChiKey: AJCZGMXDFXTFQR-FQEVSTJZSA-N

物化性质

• 沸点：
  587.7±50.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-(S)-phenylalanine piperidine amide 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 94.0h， 生成 (S)-1-piperidyl-2-(N,N-dimethylamino)-3-phenylpropane
  参考文献：
  名称：

  Chiral ligands containing heteroatoms.7. An investigation on the stereochemistry of the ketone reductions by chiral diamines/tin hydride systems.

  摘要：

  Reducing agents prepared from SnCl2, chiral diamines and diisobutyl aluminum hydride have been applied to the enantioselective reduction of alkyl phenyl and alpha-alkynyl ketones. The extent of the ee observed was dependent on the hydrolysis temperature and the structure of the chiral diamine. Hypotheses on possible mechanistic pathways on the basis of stereochemical data and H-1 NMR studies were discussed too.

  DOI：

  10.1016/s0957-4166(00)80050-6
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 、 哌啶盐酸盐 在 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以84%的产率得到N-benzyloxycarbonyl-(S)-phenylalanine piperidine amide
  参考文献：
  名称：

  Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1 S ,2 R )-tranylcypromine

  摘要：

  Primary amidations of carboxylic acids 1 or 3 with NH4Cl in the presence of ClCO2Et and Et3N were developed to afford the corresponding primary amides in 22% to quantitative yields. Additionally, we have applied the amidation to the preparation of various amides containing hydroxamic acids and achieved the synthesis of (1S,2R)-tranylcypromine as an antidepressant medicine via Lossen rearrangement. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.10.015

文献信息

• Imidazolines as amide bond replacements
  作者：Ian H. Gilbert、David C. Rees、Alan K. Crockett、Raymond C.F. Jones

  DOI：10.1016/0040-4020(95)00273-b

  日期：1995.5

  This work describes the use of a 2,5,5-trisubstituted imidazoline as an amide bond replacement. The replacement is incorporated into dipeptide derivatives of Phe, Trp, Lys and Nle and also into the CCK-4 analogue Trp-Nle-Asp-Phe-NH2 and the pentagastrin analogue Gly-Trp-Nle-Asp-Phe-NH2. The amide bond replacement is synthesised in enantiomerically and diastereomerically pure form.

  这项工作描述了2,5,5-三取代的咪唑啉作为酰胺键替代物的用途。该替代物被掺入到Phe，Trp，Lys和Nle的二肽衍生物中，并且还被掺入CCK-4类似物Trp-Nle-Asp-Phe-NH 2和五肽胃泌素类似物Gly-Trp-Nle-Asp-Phe-NH 2中。酰胺键置换以对映体和非对映体纯的形式合成。
• An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry
  作者：Tarek S. Ibrahim、Israa A. Seliem、Siva S. Panda、Amany M. M. Al-Mahmoudy、Zakaria K. M. Abdel-Samii、Nabil A. Alhakamy、Hani Z. Asfour、Mohamed Elagawany

  DOI：10.3390/molecules25112501

  日期：——

  straightforward, mild and cost-efficient synthesis of various arylamides in water was accomplished using versatile benzotriazole chemistry. Acylation of various amines was achieved in water at room temperature as well as under microwave irradiation. The developed protocol unfolds the synthesis of amino acid aryl amides, drug conjugates and benzimidazoles. The environmentally friendly synthesis, short reaction

  使用通用的苯并三唑化学完成了在水中直接、温和且经济高效地合成各种芳基酰胺。在室温下以及在微波辐射下，在水中实现了各种胺的酰化。开发的协议展开了氨基酸芳基酰胺、药物偶联物和苯并咪唑的合成。环保合成、反应时间短、后处理简单、收率高、条件温和、无外消旋化是该协议的主要优点。
• Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1 S ,2 R )-tranylcypromine
  作者：Tetsuya Ezawa、Yuya Kawashima、Takuya Noguchi、Seunghee Jung、Nobuyuki Imai

  DOI：10.1016/j.tetasy.2017.10.015

  日期：2017.12

  Primary amidations of carboxylic acids 1 or 3 with NH4Cl in the presence of ClCO2Et and Et3N were developed to afford the corresponding primary amides in 22% to quantitative yields. Additionally, we have applied the amidation to the preparation of various amides containing hydroxamic acids and achieved the synthesis of (1S,2R)-tranylcypromine as an antidepressant medicine via Lossen rearrangement. (C) 2017 Elsevier Ltd. All rights reserved.
• Chiral ligands containing heteroatoms.7. An investigation on the stereochemistry of the ketone reductions by chiral diamines/tin hydride systems.
  作者：Massimo Falorni、Giampaolo Giacomelli、Mauro Marchetti、Nicola Culeddu、Luciano Lardicci

  DOI：10.1016/s0957-4166(00)80050-6

  日期：1991.1

  Reducing agents prepared from SnCl2, chiral diamines and diisobutyl aluminum hydride have been applied to the enantioselective reduction of alkyl phenyl and alpha-alkynyl ketones. The extent of the ee observed was dependent on the hydrolysis temperature and the structure of the chiral diamine. Hypotheses on possible mechanistic pathways on the basis of stereochemical data and H-1 NMR studies were discussed too.