carbobenzyloxy glycine allyl ester | 96921-56-1

• 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: carbobenzyloxy glycine allyl ester
• 英文别名: Allyl N-(benzyloxycarbonyl)glycinate；O-allyl-N-Cbz-glycinate；Cbz-glycine allyl ester；N-CBz-allylglycine；N-benzyloxycarbonyl glycine allyl ester；N-benzyloxycarbonyl-D,L-allyl glycine；allyl N-benzyloxycarbonylglycinoate；Z-Gly-OAllyl；Prop-2-en-1-yl 2-{[(benzyloxy)carbonyl]amino}acetate；prop-2-enyl 2-(phenylmethoxycarbonylamino)acetate
• CAS: 96921-56-1
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: QXOULLJSFVPNQS-UHFFFAOYSA-N

物化性质

• 熔点：
  36-37 °C
• 沸点：
  394.4±35.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  carbobenzyloxy glycine allyl ester 生成 2-(((benzyloxy)carbonyl)amino)pent-4-enoic acid
  参考文献：
  名称：

  γ-膦酰基-γ-内酯。使用烯丙酯作为易于去除的膦酸酯保护基团

  摘要：

  在γ-位带有膦酸基团的γ-内酯的合成过程中，遇到了从相应的酯生成游离膦酸的困难。用于羧酸的保护基团适用于膦酸，使这种转化变得容易。

  DOI：

  10.1139/v85-136
• 作为产物：
  描述：

  N-苄氧羰基甘氨酸 、 (9ci)-1H-咪唑-1-羧酸-2-丙烯酯 以 乙腈 为溶剂， 反应 24.0h， 以91%的产率得到carbobenzyloxy glycine allyl ester
  参考文献：
  名称：

  On the reactivity of imidazole carbamates and ureas and their use as esterification and amidation reagents

  摘要：

  The optimization, substrate scope, and mechanism of esterification and amidation of carboxylic acids mediated by imidazole-based reagents are discussed. The innate reactivity of carbonylimidazole reagents with a range of nucleophiles is also explored. New reagents developed for the synthesis of alpha,beta-unsaturated esters are described, as are reagents for the preparation of tertiary amides directly from carboxylic acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.057

文献信息

• Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms
  作者：Simon B. Lang、Kathryn M. O'Nele、Justin T. Douglas、Jon A. Tunge

  DOI：10.1002/chem.201503644

  日期：2015.12.14

  The room temperature radical decarboxylative allylation of N‐protected α‐amino acids and esters has been accomplished via a combination of palladium and photoredox catalysis to provide homoallylic amines. Mechanistic investigations revealed that the stability of the α‐amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms.

  N保护的α-氨基酸和酯在室温下进行自由基脱羧烯丙基化反应，是通过钯和光氧化还原催化作用的组合来实现的，以提供均胺基胺。机理研究表明，由脱羧作用形成的α-氨基自由基的稳定性决定了竞争机制之间的主要反应途径。
• Iron–Nickel Dual-Catalysis: A New Engine for Olefin Functionalization and the Formation of Quaternary Centers
  作者：Samantha A. Green、Suhelen Vásquez-Céspedes、Ryan A. Shenvi

  DOI：10.1021/jacs.8b05868

  日期：2018.9.12

  electron-deficient arenes, including Lewis basic heterocycles. Here we report a highly Markovnikov-selective, dual-catalytic olefin hydroarylation that tolerates arenes and heteroarenes of any electronic character. Hydrogen atom transfer controls the formation of branched products and arene halogenation specifies attachment points on the aromatic ring. Mono-, di-, tri-, and tetra-substituted alkenes yield Markovnikov

  烯烃加氢芳基化在有机化学的两个基本构件（烯烃和芳环）之间形成碳-碳键。在没有电子偏压或导向基团的情况下，只有弗里德尔-克拉夫茨反应才允许芳烃以马尔可夫尼科夫选择性与烯烃接合以生成季碳。然而，碳阳离子的中间性阻碍了缺电子芳烃的使用，包括路易斯碱性杂环。在这里，我们报道了一种高度马尔可夫尼科夫选择性、双催化烯烃加氢芳基化，它可以容忍任何电子特征的芳烃和杂芳烃。氢原子转移控制支化产物的形成，芳烃卤化指定芳环上的连接点。单、二、三和四取代的烯烃产生马尔可夫尼科夫产物，包括非应变环内的季碳。
• Modified N-acyl-homoserine lactones as chemical probes for the elucidation of plant–microbe interactions
  作者：Heike Thomanek、Sebastian T. Schenk、Elke Stein、Karl-Heinz Kogel、Adam Schikora、Wolfgang Maison

  DOI：10.1039/c3ob41215f

  日期：——

  Gram-negative bacteria often use N-acyl-homoserine lactones (AHLs) as signal molecules to monitor their local population densities and to regulate gene-expression in a process called “Quorum Sensing” (QS). This cell-to-cell communication allows bacteria to adapt to environmental changes and to behave as multicellular communities. QS plays a key role in both bacterial virulence towards the host and symbiotic interactions with other organisms. Plants also perceive AHLs and respond to them with changes in gene expression or modifications in development. Herein, we report the synthesis of new AHL-derivatives for the investigation and identification of AHL-interacting proteins. We show that our new compounds are still recognised by different bacteria and that a novel biotin-tagged-AHL derivative interacts with a bacterial AHL receptor.

  革兰氏阴性细菌常利用N-酰基高丝氨酸内酯（AHLs）作为信号分子，监测其局部种群密度，并通过一种称为“群体感应”（Quorum Sensing，简称QS）的过程调控基因表达。这种细胞间通讯使细菌能适应环境变化，表现为多细胞社群行为。QS在细菌对宿主的毒力以及其他生物的共生相互作用中发挥关键作用。植物也能感知AHLs，并以基因表达变化或发育改变来响应它们。在此，我们报道了新型AHL衍生物的合成，用于调查和鉴定AHL相互作用蛋白。我们展示，我们的新化合物仍被不同细菌识别，且一种新型生物素标记的AHL衍生物能与细菌的AHL受体相互作用。
• γ-Phosphono-γ-lactones. The use of allyl esters as easily removable phosphonate protecting groups
  作者：Matthias Kamber、George Just

  DOI：10.1139/v85-136

  日期：1985.4.1

  During the synthesis of γ-lactones bearing a phosphonic acid group at the γ-position, difficulties were encountered generating the free phosphonic acids from corresponding esters. A protecting group used for carboxylic acids was adapted to phosphonic acids, making this transformation easy.

  在γ-位带有膦酸基团的γ-内酯的合成过程中，遇到了从相应的酯生成游离膦酸的困难。用于羧酸的保护基团适用于膦酸，使这种转化变得容易。
• Transesterification of α-Amino Esters Catalyzed by a Tetranuclear Zinc Cluster: Zn4(OCOCF3)6O
  作者：Takashi Ohshima、Kazushi Mashima、Yusuke Maegawa、Kazushi Agura、Yukiko Hayashi

  DOI：10.1055/s-0031-1290096

  日期：2012.1

  Transesterification of amino acid ester derivatives was developed using a tetranuclear zinc cluster, Zn4(OCOCF3)6O, as the catalyst. Because the reaction conditions were very mild, a variety of N-protective groups and functional groups on side chains were tolerated.

  氨基酸酯衍生物的转酯化反应采用四核锌簇 Zn4(OCOCF3)6O 作为催化剂得以发展。由于反应条件非常温和，多种 N-保护基团和侧链上的功能团均可耐受。