(异丁基碳酸)2-苯基乙酸酐 | 646055-51-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (异丁基碳酸)2-苯基乙酸酐
• 英文名称: 2-Methylpropoxycarbonyl 2-phenylacetate
• CAS: 646055-51-8
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: KXQCCPCDRSLWSU-UHFFFAOYSA-N

物化性质

• 沸点：
  321.3±35.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (异丁基碳酸)2-苯基乙酸酐 在 氨 、 水 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以0.99 g的产率得到2-苯乙酰胺
  参考文献：
  名称：

  Development of a New Nonpeptidic Self-Immolative Spacer. Application to the Design of Protease Sensing Fluorogenic Probes

  摘要：

  The design and synthesis of novel self-immolative spacer systems aiming at the release of phenol-containing compounds are described. The newly designed traceless linkers proved to be conveniently stable under physiological conditions and operate through spontaneous decomposition of an hemithioaminal intermediate under neutral aqueous conditions. Their utility was then illustrated by the preparation of original fluorogenic substrates of penicillin amidase whose strong fluorescence is unveiled through enzyme-initiated domino reactions.

  DOI：

  10.1021/ol800198f
• 作为产物：
  描述：

  苯乙酸 、 氯甲酸异丁酯 在 N-甲基吗啉 作用下， 以 乙酸乙酯 为溶剂， 反应 0.67h， 生成 (异丁基碳酸)2-苯基乙酸酐
  参考文献：
  名称：

  由酸酐进行的苯甲硒酸酯的一般，轻度和无金属合成及其在肽合成中的用途

  摘要：

  开发了一种温和，实用和简单的方法，用于从几种酸酐和二苯基二硒化物合成苯基硒酸酯。这种无过渡金属的方法可以直接进入可存储的Fmoc-氨基酸硒酸酯，它们是有效的化学选择性酰化试剂。说明了在寡肽合成中的应用。

  DOI：

  10.1021/acs.joc.7b00173

文献信息

• Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones
  作者：David K. Romney、Sean M. Colvin、Scott J. Miller

  DOI：10.1021/ja508757g

  日期：2014.10.8

  We report a peptide-based catalyst that can strongly influence the regio- and enantioselectivity of the Baeyer–Villiger (BV) oxidation of cyclic ketones bearing amide, urea, or sulfonamide functional groups. Both types of selectivity are thought to arise from a catalyst–substrate hydrogen-bonding interaction. Furthermore, in selected cases, the reactions exhibit the hallmarks of parallel kinetic resolution

  我们报告了一种基于肽的催化剂，它可以强烈影响带有酰胺、尿素或磺酰胺官能团的环酮的 Baeyer-Villiger (BV) 氧化的区域和对映选择性。两种类型的选择性都被认为是由催​​化剂-底物氢键相互作用引起的。此外，在选定的情况下，反应表现出平行动力学分辨率的标志。在不对称过程中使用催化在 BV 产品之间进行选择的能力可能对复杂分子（包括天然产品）的合成和多样化具有广泛的用途。
• A facile synthesis of 5-alkoxypyrrol-2(5H)-ones using a modified aza-Achmatowicz oxidation
  作者：Sezgin Kiren、Xuechuan Hong、Carolyn A. Leverett、Albert Padwa

  DOI：10.1016/j.tet.2009.03.011

  日期：2009.8

  An efficient approach to 2,4-disubstituted pyrroles has been uncovered and is based on an oxidative rearrangement of a furanyl carbamate followed by sequential reaction of the resulting 5-methoxypyrrol-2(5H)-one with various alkyl lithiates. The final step of the procedure involves heating the ring opened 1-methoxy-5-oxopentylcarbamate with a primary amine. The overall process can be carried out under mild conditions and complements existing methods to prepare 2,4-disubstituted pyrroles. (C) 2009 Elsevier Ltd. All rights reserved.
• General, Mild, and Metal-Free Synthesis of Phenyl Selenoesters from Anhydrides and Their Use in Peptide Synthesis
  作者：Andrea Temperini、Francesca Piazzolla、Lucio Minuti、Massimo Curini、Carlo Siciliano

  DOI：10.1021/acs.joc.7b00173

  日期：2017.5.5

  A mild, practical, and simple procedure for phenyl selenoesters synthesis from several anhydrides and diphenyl diselenide was developed. This transition-metal-free method provides a straightforward entry to storable Fmoc-amino acid selenoesters which are effective chemoselective acylating reagents. An application to oligopeptide synthesis was illustrated.

  开发了一种温和，实用和简单的方法，用于从几种酸酐和二苯基二硒化物合成苯基硒酸酯。这种无过渡金属的方法可以直接进入可存储的Fmoc-氨基酸硒酸酯，它们是有效的化学选择性酰化试剂。说明了在寡肽合成中的应用。
• Development of a New Nonpeptidic Self-Immolative Spacer. Application to the Design of Protease Sensing Fluorogenic Probes
  作者：Yves Meyer、Jean-Alexandre Richard、Marc Massonneau、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1021/ol800198f

  日期：2008.4.1

  The design and synthesis of novel self-immolative spacer systems aiming at the release of phenol-containing compounds are described. The newly designed traceless linkers proved to be conveniently stable under physiological conditions and operate through spontaneous decomposition of an hemithioaminal intermediate under neutral aqueous conditions. Their utility was then illustrated by the preparation of original fluorogenic substrates of penicillin amidase whose strong fluorescence is unveiled through enzyme-initiated domino reactions.