L-(+)-N-boc-2-苯基甘氨酸酰肼 | 1043912-48-6

• 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
• 中文名称: L-(+)-N-boc-2-苯基甘氨酸酰肼
• 英文名称: L-(+)-N-BOC-phenylglycine hydrazide
• 英文别名: L-(+)-N-Boc-2-phenylglycine hydrazide；tert-butyl N-[(1S)-2-hydrazinyl-2-oxo-1-phenylethyl]carbamate
• CAS: 1043912-48-6
• 化学式: C₁₃H₁₉N₃O₃
• 分子量: 265.312
• InChiKey: UGJVDHKUPLYPDD-JTQLQIEISA-N

物化性质

• 熔点：
  105-107 °C(Solv: hexane (110-54-3); methanol (67-56-1))
• 沸点：
  486.6±45.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-(+)-N-boc-2-苯基甘氨酸酰肼 在 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.75h， 生成 1-((S)-(5-(benzylthio)-1,3,4-oxadiazol-2-yl)(phenyl)methyl)-3-(4-nitrophenyl)urea
  参考文献：
  名称：

  Targeting RECQL5 Functions, by a Small Molecule, Selectively Kills Breast Cancer in Vitro and in Vivo

  摘要：

  DOI：

  10.1021/acs.jmedchem.0c01692
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-L-phenylglycine methyl ester 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以66%的产率得到L-(+)-N-boc-2-苯基甘氨酸酰肼
  参考文献：
  名称：

  从对映体苯基甘氨酸酰肼高效合成新的2-氨基甲基-1,3,4-恶二唑

  摘要：

  在冰乙酸的存在下，在N-保护的苯基甘氨酸酰肼与原酸三乙酯（原甲酸，原乙酸，原丙酸，原苯甲酸酯）的反应中合成了2-氨基甲基-1,3,4-恶二唑的新衍生物。研究了对酸敏感的裂解反应Ñ -BOC和Ñ被-Ac 1,3,4-恶二唑呈现。分光特性小号的化合物和试图阐明产品中观察到的现象消旋的进行了讨论。

  DOI：

  10.1016/j.tet.2008.11.096

文献信息

• An efficient synthesis of new 2-aminomethyl-1,3,4-oxadiazoles from enantiomeric phenylglycine hydrazides
  作者：Agnieszka Kudelko、Wojciech Zieliński

  DOI：10.1016/j.tet.2008.11.096

  日期：2009.2

  New derivatives of 2-aminomethyl-1,3,4-oxadiazole were synthesized in the reactions of N-protected phenylglycine hydrazides and triethyl orthoesters (orthoformate, orthoacetate, orthopropionate, orthobenzoate) in the presence of glacial acetic acid. Studies on the cleavage reactions of the acid-sensitive N-BOC and N-Ac 1,3,4-oxadiazoles are presented. Spectral characteristics of the compounds and attempts

  在冰乙酸的存在下，在N-保护的苯基甘氨酸酰肼与原酸三乙酯（原甲酸，原乙酸，原丙酸，原苯甲酸酯）的反应中合成了2-氨基甲基-1,3,4-恶二唑的新衍生物。研究了对酸敏感的裂解反应Ñ -BOC和Ñ被-Ac 1,3,4-恶二唑呈现。分光特性小号的化合物和试图阐明产品中观察到的现象消旋的进行了讨论。
• New <i>N</i>-substituted hydrazones, derivatives of uridyl aldehyde
  作者：Katarzyna Kral、Tadeusz Bieg、Agnieszka Kudelko、Anna Barabaś、Aleksandra Dąbrowska、Ilona Wandzik

  DOI：10.1080/15257770.2016.1231321

  日期：2017.3.4

  ABSTRACT N-substituted isomeric hydrazones of uridyl aldehyde have been synthesized. The occurrence of the dominant E isomers with respect to the azomethine group was confirmed by means of NMR spectroscopy. Synthesized hydrazones feature an acetonide moiety as a protection of two hydroxyl groups on the ribose part. The attempt to remove the protecting group resulted in an azo-hydrazone tautomeric mixture

  摘要已合成了尿苷醛的 N-取代异构腙。通过NMR光谱证实存在关于偶氮甲碱基团的主要E异构体。合成的腙具有丙酮化物部分作为核糖部分上两个羟基的保护。去除保护基团的尝试产生了偶氮腙互变异构混合物。所述化合物可能是用于金属螯合的有价值的手性配体。对锰 (II) 离子对一种选定腙的亲和力进行了评估。
• Facile one-pot synthesis of 2-amino-1,3,4-oxadiazole tethered peptidomimetics by molecular-iodine-mediated cyclodeselenization
  作者：L. Santhosh、C. Srinivasulu、S. Durgamma、Girish Prabhu、Vommina V. Sureshbabu

  DOI：10.1039/c7nj02278f

  日期：——

  Synthesis of 2-amino-1,3,4-oxadiazole tethered peptidomimetics through the reaction of Nα-protected amino acid hydrazides with isoselenocyanato esters in one- pot is described. The molecular-iodine-mediated cyclodeselenization of in situ generated selenosemicarbazide intermediates resulted in the facile formation of 2-amino-1,3,4-oxadiazoles under mild conditions in excellent yields. The method employs

  描述了通过一锅中Nα-保护的氨基酸酰肼与异戊烯基氰基酸酯的反应合成2-氨基-1,3,4-恶二唑束缚的拟肽。分子碘介导的原位生成的硒代氨基脲化合物中间体的环二硒化导致在温和条件下以优异的产率容易地形成2-氨基-1,3,4-恶二唑。该方法采用对环境无害的碘作为环化剂，从而避免了现有路线中所采用的苛刻条件。
• Exploring the reaction of formaldehyde with α-<i>N</i>-protected amino acid hydrazides
  作者：Giancarlo Verardo、Paola Geatti、Marta Mancuso、Paolo Strazzolini

  DOI：10.1139/v08-061

  日期：2008.7.1

  The reaction of formaldehyde with enantiomerically pure α-N-protected amino acid hydrazides is described. The system has been investigated in different solvents, including both aqueous formaldehyde and paraformaldehyde, with the aim of simplifying the final reaction mixture. Aqueous formaldehyde in refluxing THF proved to be the best combination, affording mainly the corresponding monomeric N-methylene

  描述了甲醛与对映异构纯 α-N-保护的氨基酸酰肼的反应。该系统已在不同的溶剂中进行了研究，包括甲醛水溶液和多聚甲醛，目的是简化最终反应混合物。回流四氢呋喃中的含水甲醛被证明是最佳组合，主要提供相应的单体 N-亚甲基和 1,3,5-三取代-1,3,5-六氢三嗪衍生物。1H 和 13C NMR 光谱证明，单体形式是高温下唯一存在的形式。关键词：氨基酸酰肼，甲醛，缩合反应，单体N-亚甲基衍生物，低聚物。
• A facile one-pot synthesis of Nα-Z/Boc-protected S-linked 1,3,4-oxadiazole tethered peptidomimetics
  作者：Vommina V. Sureshbabu、B. Vasantha、G. Nagendra

  DOI：10.1016/j.tetlet.2011.12.093

  日期：2012.3

  A new class of S-linked 1,3,4-oxadiazole-tethered N-alpha-protected peptidomimetics is designed and synthesized by a reaction of N-alpha-Z/Boc-protected 1,3,4-oxadiazole-2-thiol with alpha-bromo ester derived from amino acid. The protocol has also been employed for the synthesis of glycosylated amino acids and N,N'-orthogonally protected dipeptidomimetics bearing S-linked 1,3,4-oxadiazole mimetics as well. The intermediate 5-alkyl amino-1,3,4-oxadiazole-2-thiols have been isolated as stable compounds. Further, the chain extension at both N- and C-termini of N-protected S-linked 1,3,4-oxadiazole tethered dipeptidomimetics was also demonstrated. (C) 2012 Elsevier Ltd. All rights reserved.