Cbz-L-Phe-cyclohexylNH | 17186-45-7

• 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: Cbz-L-Phe-cyclohexylNH
• 英文别名: N-benzyloxycarbonyl-L-phenylalanine cyclohexylamide；N-Benzyloxycarbonyl-L-phenylalanin-cyclohexylamid；N-Benzyloxycarbonyl-L-phenylalanin-cyclohexylamid；benzyl N-[(2S)-1-(cyclohexylamino)-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 17186-45-7
• 化学式: C₂₃H₂₈N₂O₃
• 分子量: 380.487
• InChiKey: JNOPAYROMBBZSP-NRFANRHFSA-N

物化性质

• 熔点：
  165 °C
• 沸点：
  624.3±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  Cbz-L-Phe-cyclohexylNH 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 74.0h， 生成 (S)-N-Cyclohexyl-2-{[(4-methyl-6-phenyl-pyrimidin-2-yl)-phenyl-methyl]-amino}-3-phenyl-propionamide
  参考文献：
  名称：

  3-苯基异恶唑并[2,3- a ]嘧啶衍生物的亲核开环中的立体选择性和区域选择性。不可预料的二聚化和环转化。嘧啶基甲胺，嘧啶基甲基氨基酸酰胺和α-氨基-2-嘧啶基乙酰胺的衍生物的合成1

  摘要：

  光学活性氨基酸酰胺和麻黄碱在2-氧代-3-苯基异恶唑啉[2,3- a ]嘧啶衍生物中异恶唑酮环的亲核开环导致嘧啶基甲基氨基酸酰胺。的不同使用酰胺升-氨基酸和（ - ） -麻黄碱导致不同程度的立体选择性的。选择性的程度主要取决于所使用的亲核试剂。当使用羟胺如麻黄碱时，发现通过仲氨基的进攻是有利的区域选择性。取代苯基异恶唑[2,3- a]中位置2的氧代基团后通过亚氨基形成]嘧啶体系，预期不会发生开环后的自发脱羧反应，从而获得了2-嘧啶基乙酰胺的氨基酸酰胺衍生物，该衍生物与嘧啶溴酸（博来霉素的重要成分）密切相关，用于癌症治疗。然而，通过在溶液中加热5，7-二甲基-2-亚氨基-3-苯基异恶唑并[2，3- a ]嘧啶，它经历了前所未有的二聚反应过程，该过程涉及苯基和亚氨基。通过乙酰化保护亚氨基后，亲核试剂可能会开环，导致形成2-嘧啶基乙酰胺的衍生物。2-乙酰氨基-5,7-二甲基-3-苯基异恶唑[2,3-

  DOI：

  10.1021/jo0497196
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 三氧化硫 、 N,N-二甲基甲酰胺 作用下， 生成 Cbz-L-Phe-cyclohexylNH
  参考文献：
  名称：

  Distress and disease status among patients with rheumatoid arthritis: Roles of coping styles and perceived responses from support providers

  摘要：

  Previous research has shown that social support can have a beneficial impact on coping processes and psychological adjustment in patients with rheumatoid arthritis (RA). The association of individual coping styles and perceived responses from others to one's pain episodes with patients' distress and disease status over time was investigated. The sample consisted of 42 middle-aged patients with RA who were predominantly White (98%), female (64%), and married (88%). Participants completed surveys and their rheumatologist completed clinical assessments of patient disease status at 2 time points over a 9-month period Although punishing responses from others (e.g, getting irritated or angry when the patient is in pain) were perceived as relatively infrequent, they were associated with a patient coping style of focusing on and venting of negative emotion as well as elevated negative affect (NA). Findings also indicated that those who perceived punishing responses from close others and coped by venting negative emotions reported increased NA over time and were rated by their rheumatologist as having more severe RA disease status over time. Implications for psychosocial intervention and directions for future research are discussed.

  DOI：

  10.1207/s15324796abm2302_8

文献信息

• Biocatalytic hydrolysis of various anilides containing l-phenylalanine using Baker's yeast under starvation conditions
  作者：Takuya Noguchi、Hideyuki Daitoku、Shin Satoh、Yuya Kawashima、Nobuyuki Imai

  DOI：10.1016/j.tetlet.2022.154130

  日期：2022.10

  Biocatalytic hydrolysis of various anilides containing l-phenylalanine using Baker's yeast proceeded efficiently without sucrose under neutral conditions to afford the corresponding aniline derivatives in 26–60% yields.

  在中性条件下，在不含蔗糖的情况下，使用贝克酵母对各种含有l-苯丙氨酸的苯胺的生物催化水解有效地进行，以 26-60% 的产率提供相应的苯胺衍生物。
• An Efficient Light‐Mediated Protocol for the Direct Amide Bond Formation via a Novel Carboxylic Acid Photoactivation Mode by Pyridine‐CBr₄
  作者：Olga G. Mountanea、Danai Psathopoulou、Christiana Mantzourani、Maroula G. Kokotou、E. Alexandros Routsi、Demeter Tzeli、Christoforos G. Kokotos、George Kokotos

  DOI：10.1002/chem.202300556

  日期：2023.6.22

  A UVA-light-mediated synthesis of amides from carboxylic acids and amines or amino acids is presented, taking advantage of a novel photoactivation mode using pyridine-CBr4. Mechanistic studies by DI-HRMS provide experimental evidence for the formation of various intermediates. Application in the synthesis of industrially interesting or bioactive compounds was demonstrated.

  提出了利用吡啶-CBr 4的新型光活化模式，由羧酸和胺或氨基酸UVA光介导合成酰胺。DI-HRMS 的机理研究为各种中间体的形成提供了实验证据。展示了在工业上有趣的或生物活性化合物的合成中的应用。
• Verfahren zur Herstellung von Carbonsäureamidgruppen enthaltenden Verbindungen, insbesondere von Peptiden
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0135183A2

  公开（公告）日：1985-03-27

  Die Erfindung betrifft ein Verfahren zur Herstellung von Carbonsäureamidgruppen enthaltenden Verbindungen, insbesondere Peptiden durch Umsetzung von Verbindungen, die eine Carboxylgruppe enthalten, in Gegenwart von Dialkylphosphinsäureanhydriden mit Verbindungen, die eine freie Aminogruppe enthalten, das dadurch gekennzeichnet ist, daß man die Wasserstoffionenkonzentration der Reaktionsmischung durch Zudosierung einer Base während der Reaktion innerhalb eines definierten Bereiches hält und nach beendeter Reaktion gegebenenfalls zum Schutz anderer funktioneller Gruppen eingeführte Reste abspaltet.

  本发明涉及一种制备含羧酸酰胺基团的化合物（尤其是肽）的工艺，该工艺是通过使含羧基的化合物在二烷基膦酸酐存在下与含游离氨基的化合物反应来制备肽的，其特点是通过在反应过程中加入碱，使反应混合物的氢离子浓度保持在规定的范围内，并且在反应完成后，消除为保护其他官能团而引入的任何残留物。
• 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.
• Distress and disease status among patients with rheumatoid arthritis: Roles of coping styles and perceived responses from support providers
  作者：Kenneth W. Griffin、Ronald Friend、Alan T. Kaell、Ronald S. Bennett

  DOI：10.1207/s15324796abm2302_8

  日期：2001.5

  Previous research has shown that social support can have a beneficial impact on coping processes and psychological adjustment in patients with rheumatoid arthritis (RA). The association of individual coping styles and perceived responses from others to one's pain episodes with patients' distress and disease status over time was investigated. The sample consisted of 42 middle-aged patients with RA who were predominantly White (98%), female (64%), and married (88%). Participants completed surveys and their rheumatologist completed clinical assessments of patient disease status at 2 time points over a 9-month period Although punishing responses from others (e.g, getting irritated or angry when the patient is in pain) were perceived as relatively infrequent, they were associated with a patient coping style of focusing on and venting of negative emotion as well as elevated negative affect (NA). Findings also indicated that those who perceived punishing responses from close others and coped by venting negative emotions reported increased NA over time and were rated by their rheumatologist as having more severe RA disease status over time. Implications for psychosocial intervention and directions for future research are discussed.