N-allyloxycarbonyl-D-phenyl-glycine | 104128-14-5

• 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-allyloxycarbonyl-D-phenyl-glycine
• 英文别名: (2R)-{[(allyloxy)carbonyl]amino}(phenyl)acetic acid；(R)-2-(((Allyloxy)carbonyl)amino)-2-phenylacetic acid；(2R)-2-phenyl-2-(prop-2-enoxycarbonylamino)acetic acid
• CAS: 104128-14-5
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: VKLQWRQOSFXTSM-SNVBAGLBSA-N

物化性质

• 沸点：
  409.7±45.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-allyloxycarbonyl-D-phenyl-glycine 在 四(三苯基膦)钯 2-乙基-己酸稀土盐 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of 3-heterosubstituted isocephem and iso-oxacephem antibiotics

  摘要：

  DOI：

  10.1016/s0040-4039(00)84003-4
• 作为产物：
  描述：

  左旋苯甘氨酸 、 氯甲酸烯丙酯 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以99%的产率得到N-allyloxycarbonyl-D-phenyl-glycine
  参考文献：
  名称：

  Mild non-transition metal catalyzed deprotection of N-allyloxycarbonyl amines

  摘要：

  A synthesis of mehyl (2S)-2-amino-2,4-diphenylbutanoate has been achieved via a novel one-pot non-transition metal mediated deprotection of the N-allyloxycarbonyl amine using iodine in wet acetonitrile. The applicability of this transformation has been demonstrated by deprotecting a variety of N-allyloxycarbonyl amines, alpha-aminomethyl esters and simple N-allyloxycarbonyl alkyl amines. Deprotection occurs in high yield (82-93%) without erosion of the optical purity of the chiral substrates. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.064

文献信息

• Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis
  作者：Eiji Yamamoto、Kodai Wakafuji、Yuho Furutachi、Kaoru Kobayashi、Takashi Kamachi、Makoto Tokunaga

  DOI：10.1021/acscatal.8b00693

  日期：2018.7.6

  Asymmetric base hydrolysis of α-chiral esters with synthetic small-molecule catalysts is described. Quaternary ammonium salts derived from quinine were used as chiral phase-transfer catalysts to promote the base hydrolysis of N-protected amino acid hexafluoroisopropyl esters in a CHCl3/NaOH (aq) via dynamic kinetic resolution, providing the corresponding products in moderate to good yields (up to 99%)

  描述了用合成的小分子催化剂对α-手性酯的不对称碱水解。奎宁衍生的季铵盐用作手性相转移催化剂，可通过动态动力学拆分促进CHCl 3 / NaOH（aq）中N保护的氨基酸六氟异丙基酯的碱水解，以中等至良好的收率提供相应的产物（最高99％）和最高96：4 er。使用DFT计算和伪过渡态（pseudo-TS）构象搜索进行的实验和计算机制研究提供了考虑立体选择性起源的TS模型。该模型表明，π-堆积和H-键相互作用在稳定TS结构中起重要作用。
• Synthesis and in vitro antibacterial activities of 3-thiazol 4 yl-carba-l-dethiacephalosporins.
  作者：WILLIAM J. HORNBACK、JOHN E. MUNROE、FRED T. COUNTER

  DOI：10.7164/antibiotics.47.1052

  日期：——

  The synthesis and microbiological evaluation of a new series of 3-thiazol-4-yl-carba-1-dethiacephalosporins is described. Structure activity relationship was achieved by changing substitution at the 2-position of the thiazole moiety. The result was a marked variance of microbiological activity in the C7 side-chain derivatives. ATMO derivatives possess potent activity against both Gram-positive and Gram-negative bacteria. For example, MICs (μg/ml) of LY215226 against representative organisms are as follows: S. aureus 0.25, S. pneumoniae 0.008, H. influenzae 0.008, E. coli 0.25, K. pneumoniae 0.008, E. cloacae 0.5, S. typhi 0.25, and M. morganii 0.25.

  描述了一系列新的3-噻唑-4-基-卡巴-1-去硫头孢菌素的合成和微生物学评估。通过改变噻唑部分的2位取代来实现结构-活性关系。结果表明，C7侧链衍生物在微生物活性上存在明显差异。ATMO衍生物对革兰阳性和革兰阴性细菌均具有强效活性。例如，LY215226对典型微生物的最低抑菌浓度（MIC，μg/ml）如下：金黄色葡萄球菌0.25，肺炎链球菌0.008，流感嗜血杆菌0.008，大肠杆菌0.25，肺炎克雷伯菌0.008，克隆氏菌0.5，伤寒沙门氏菌0.25，以及摩根氏菌0.25。
• MUNROE, JOHN E.
  作者：MUNROE, JOHN E.

  DOI：——

  日期：——
• Synthesis of 3-heterosubstituted isocephem and iso-oxacephem antibiotics
  作者：Stuart W. McCombie、William A. Metz、Adriano Afonso

  DOI：10.1016/s0040-4039(00)84003-4

  日期：1986.1
• Mild non-transition metal catalyzed deprotection of N-allyloxycarbonyl amines
  作者：Ronald H. Szumigala、Ekama Onofiok、Sandor Karady、Joseph D. Armstrong、Ross A. Miller

  DOI：10.1016/j.tetlet.2005.04.064

  日期：2005.6

  A synthesis of mehyl (2S)-2-amino-2,4-diphenylbutanoate has been achieved via a novel one-pot non-transition metal mediated deprotection of the N-allyloxycarbonyl amine using iodine in wet acetonitrile. The applicability of this transformation has been demonstrated by deprotecting a variety of N-allyloxycarbonyl amines, alpha-aminomethyl esters and simple N-allyloxycarbonyl alkyl amines. Deprotection occurs in high yield (82-93%) without erosion of the optical purity of the chiral substrates. (c) 2005 Elsevier Ltd. All rights reserved.