tert-butyl (S)-3-(((benzyloxy)carbonyl)amino)-4-phenylbutanoate | 200267-79-4

• 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: tert-butyl (S)-3-(((benzyloxy)carbonyl)amino)-4-phenylbutanoate
• 英文别名: (S)-3-Benzyloxycarbonylamino-4-phenyl-butyric acid tert-butyl ester；tert-butyl (3S)-4-phenyl-3-(phenylmethoxycarbonylamino)butanoate
• CAS: 200267-79-4
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: ZEVUWVOKKACHRQ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-3-(((benzyloxy)carbonyl)amino)-4-phenylbutanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (3S)-3-氨基-4-苯基丁酸叔丁酯
  参考文献：
  名称：

  New kelatorphan-related inhibitors of enkephalin metabolism: improved antinociceptive properties

  摘要：

  In order to improve the in vivo protection of enkephalins from enzymatic degradation, a new series of inhibitors derived from kelatorphan [HONHCOCH2CH(CH2Ph)CONHCH(CH3)COOH], the first-described complete inhibitor of enkephalin metabolism, were designed by modification of the C-terminal amino acid. The progressive lengthening of the chain of this residue shows that a beta-alanine seems to be the best basic model for the conception of such types of compounds. On the other hand, the methylation of the amide bond, which is well accepted by aminopeptidase N (EC 3.4.11.2) and dipeptidylaminopeptidase, induced a significant loss of affinity for neutral endopeptidase -24.11. Starting from these data, compounds containing a variously substituted beta-alanine residue and corresponding to the general formula HONHCOCH2CH(CH2Ph)CONHCH(R1)CH(R2)COOH were synthesized. All these molecules inhibit neutral endopeptidase -24.11 and dipeptidylaminopeptidase in the nanomolar range, and those containing an aromatic chain (compound 7A, R1 = CH2Ph,R2 = H, and compound 8A, R1 = Ph, R2 = H) inhibit the biologically relevant aminopeptidase N, with IC50's around 10(-8) M. Intracerebroventricular injection in mice of these multienzyme inhibitors produced an efficient and naloxone-reversible analgesic response (hot plate test): compounds 7A and 8A were shown to be more potent than kelatorphan in increasing the jump latency time, in agreement with their in vitro properties, and these new compounds were found to increase the forepaw lick latency, a reflex considered as a typical morphine response.

  DOI：

  10.1021/jm00127a017
• 作为产物：
  描述：

  L-苯丙氨酸 在 氯甲酸乙酯 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 8.08h， 生成 tert-butyl (S)-3-(((benzyloxy)carbonyl)amino)-4-phenylbutanoate
  参考文献：
  名称：

  用于实时阳光诱导乙烯酮形成和 API 合成的太阳能跟踪器集成微反应器

  摘要：

  利用太阳能进行化学合成是地球上最重要的反应途径之一。本文提出了一种集成的程序化太阳能电池板微流平台方法，用于 Wolff 重排以合成 β-氨基酸、酯、酰胺、硫醇盐等。该反应在没有金属催化剂的情况下进行，并以一种省时省力的方式使用阳光作为能源，从而实现了一种更环保的方法。合成的同源酸进一步扩展到抗糖尿病 2 型活性药物成分 (API) 前列列汀的合成。

  DOI：

  10.1039/d2gc00649a

文献信息

• [EN] THROMBIN INHIBITORS<br/>[FR] INHIBITEURS DE LA THROMBINE
  申请人：NOVARTIS AG

  公开号：WO1997046553A1

  公开（公告）日：1997-12-11

  (EN) The present invention provides a compound of general formula (I) in which Y is a primary or secondary amino group; R2 is the residue of a natural or synthetic amino acid; R3 is hydrogen or a C1-C8 alkyl chain which may be substituted by hydroxy or halogen; and X is (CH2)n where n is 1, 2, or 3, or is CH2N or represents a fused phenyl ring which is optionally substituted by one or two methoxy groups or a salt thereof.(FR) L'invention concerne un composé de formule générale (I), ou son sel, formule dans laquelle Y est un groupe amino primaire ou secondaire; R2 est le résidu d'un acide aminé naturel ou synthétique; R3 est hydrogène ou une chaîne alkyle C1-C8 qu'on peut substituer par hydroxy ou halogène; et X est (CH2)n où n est égal à 1, 2 ou 3, ou bien est CH2N ou représente un noyau phénylique condensé éventuellement substitué par un ou deux groupes méthoxy.

  本发明提供了通式（I）的化合物，其中Y是一级或二级氨基团；R2是天然或合成氨基酸的残基；R3是氢或C1-C8烷基链，可以被羟基或卤素取代；X是（CH2）n，其中n为1、2或3，或者是CH2N或代表一个融合的苯环，该环可以选择地被一个或两个甲氧基取代，或其盐。
• New kelatorphan-related inhibitors of enkephalin metabolism: improved antinociceptive properties
  作者：Juan Xie、Jean Marc Soleilhac、Catherine Schmidt、Jacques Peyroux、Bernard P. Roques、Marie Claude Fournie-Zaluski

  DOI：10.1021/jm00127a017

  日期：1989.7

  In order to improve the in vivo protection of enkephalins from enzymatic degradation, a new series of inhibitors derived from kelatorphan [HONHCOCH2CH(CH2Ph)CONHCH(CH3)COOH], the first-described complete inhibitor of enkephalin metabolism, were designed by modification of the C-terminal amino acid. The progressive lengthening of the chain of this residue shows that a beta-alanine seems to be the best basic model for the conception of such types of compounds. On the other hand, the methylation of the amide bond, which is well accepted by aminopeptidase N (EC 3.4.11.2) and dipeptidylaminopeptidase, induced a significant loss of affinity for neutral endopeptidase -24.11. Starting from these data, compounds containing a variously substituted beta-alanine residue and corresponding to the general formula HONHCOCH2CH(CH2Ph)CONHCH(R1)CH(R2)COOH were synthesized. All these molecules inhibit neutral endopeptidase -24.11 and dipeptidylaminopeptidase in the nanomolar range, and those containing an aromatic chain (compound 7A, R1 = CH2Ph,R2 = H, and compound 8A, R1 = Ph, R2 = H) inhibit the biologically relevant aminopeptidase N, with IC50's around 10(-8) M. Intracerebroventricular injection in mice of these multienzyme inhibitors produced an efficient and naloxone-reversible analgesic response (hot plate test): compounds 7A and 8A were shown to be more potent than kelatorphan in increasing the jump latency time, in agreement with their in vitro properties, and these new compounds were found to increase the forepaw lick latency, a reflex considered as a typical morphine response.
• A solar tracker integrated microreactor for real-time sunlight induced ketene formation and API synthesis
  作者：Abhilash Rana、Bhanwar Kumar Malviya、Deepak Kumar Jaiswal、P. Srihari、Ajay K. Singh

  DOI：10.1039/d2gc00649a

  日期：——

  Employing solar energy for chemical synthesis is one of the most important reaction pathways on the earth. An integrated programmed solar panel micro-flow platform approach is presented herein for Wolff rearrangements to synthesize β-amino acid, ester, amide, thiolate, etc. The reaction is performed without a metal catalyst and uses sunlight as an energy source in a time and labour-efficient manner

  利用太阳能进行化学合成是地球上最重要的反应途径之一。本文提出了一种集成的程序化太阳能电池板微流平台方法，用于 Wolff 重排以合成 β-氨基酸、酯、酰胺、硫醇盐等。该反应在没有金属催化剂的情况下进行，并以一种省时省力的方式使用阳光作为能源，从而实现了一种更环保的方法。合成的同源酸进一步扩展到抗糖尿病 2 型活性药物成分 (API) 前列列汀的合成。