4-bromobenzyl 4-nitrobenzoate | 53218-06-7

• 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: 4-bromobenzyl 4-nitrobenzoate
• 英文别名: 4-nitro-benzoic acid-(4-bromo-benzyl ester)；4-Nitro-benzoesaeure-(4-brom-benzylester)；p-Nitrobenzoesaeure-(p-brombenzylester)；(4-bromophenyl)methyl 4-nitrobenzoate
• CAS: 53218-06-7
• 化学式: C₁₄H₁₀BrNO₄
• 分子量: 336.142
• InChiKey: AHKHWSYPMKYMGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2916399090

反应信息

• 作为产物：
  描述：

  4-溴苄醇 、 对硝基苯甲酸 在 碘苯二乙酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以85%的产率得到4-bromobenzyl 4-nitrobenzoate
  参考文献：
  名称：

  3,5-二硝基苯甲酸的有机催化光信反应

  摘要：

  已经开发了使用 3,5-二硝基苯甲酸作为亲核试剂的有机催化 Mitsunobu 反应的第二代程序。与原始程序中使用的 4-硝基苯甲酸相比，这种酸的酸度增加，可以提高所需产物的分离产率，并消除不需要的乙酸盐副产物的形成。

  DOI：

  10.1055/s-0029-1219795

文献信息

• Vitamin B1-catalyzed aerobic oxidative esterification of aromatic aldehydes with alcohols
  作者：Xin-Long Luo、Danhua Ge、Zi-Lun Yu、Xue-Qiang Chu、Pei Xu

  DOI：10.1039/d1ra05134b

  日期：——

  A straightforward aerobic oxidative esterification of aryl aldehydes with alcohols has been developed for the synthesis of substituted esters by employing vitamin B1 as a cost-effective, metal-free, and eco-friendly NHC catalyst. Air is used as a green terminal oxidant. The reaction is a useful addition to the existing NHC-catalytic oxidative esterification.

  已经开发了一种直接的芳基醛与醇的好氧氧化酯化反应，通过使用维生素 B1 作为一种经济高效、无金属且环保的 NHC 催化剂来合成取代酯。空气被用作绿色终端氧化剂。该反应是对现有 NHC 催化氧化酯化的有用补充。
• Organocatalytic Mitsunobu Reactions
  作者：Tracy Yuen Sze But、Patrick H. Toy

  DOI：10.1021/ja063141v

  日期：2006.8.1

  A catalytic Mitsunobu reaction system is described in which the azo reagent is used as an organocatalyst and iodosobenzene diacetate is used as the stoichiometric oxidant. In this system, iodosobenzene diacetate oxidizes the formed hydrazine byproduct to regenerate the azo reagent. Yields obtained in the catalytic reactions using a variety of carboxylic acids and alcohols were slightly lower than those

  描述了一种催化性的 Mitsunobu 反应系统，其中偶氮试剂用作有机催化剂，碘代苯二乙酸酯用作化学计量氧化剂。在该系统中，碘代苯二乙酸盐氧化形成的肼副产物以再生偶氮试剂。在使用各种羧酸和醇的催化反应中获得的产率略低于从相应化学计量反应获得的产率。伯醇和仲醇都可以用作该反应体系中的底物，仲醇在甲醇中心提供具有倒立立体化学的产物。
• Monomer-on-Monomer (MoM) Mitsunobu Reaction: Facile Purification Utilizing Surface-Initiated Sequestration
  作者：Pradip K. Maity、Alan Rolfe、Thiwanka B. Samarakoon、Saqib Faisal、Ryan D. Kurtz、Toby R. Long、Alexander Schätz、Daniel L. Flynn、Robert N. Grass、Wendelin J. Stark、Oliver Reiser、Paul R. Hanson

  DOI：10.1021/ol1022382

  日期：2011.1.7

  A monomer-on-monomer (MoM) Mitsunobu reaction utilizing norbornenyl-tagged (Nb-tagged) reagents is reported, whereby purification was rapidly achieved by employing ring-opening metathesis polymerization, which was initiated by any of three methods utilizing Grubbs catalyst: (i) free catalyst in solution, (ii) surface-initiated catalyst-armed silica, or (iii) surface-initiated catalyst-armed Co/C magnetic nanoparticles.
• Dimethylbut-2-ynedioate mediated esterification of acids via sp3 C–N bond cleavage of benzylic tertiary amines
  作者：Hao Shen、Xing Lu、Ke-Zhi Jiang、Ke-Fang Yang、Yixin Lu、Zhan-Jiang Zheng、Guo-Qiao Lai、Li-Wen Xu

  DOI：10.1016/j.tet.2012.08.024

  日期：2012.10

  A straightforward synthetic transformation of tertiary amines to the esterification of equimolar amounts of acids was demonstrated in this manuscript. The present protocol can be regarded as a straightforward synthetic transformation of tertiary amines to the esterification of equimolar amounts of acid. Moreover, the reaction is fundamentally new chemistry for the sp(3) C-N bond cleavage coupled with esterification. The esterification reaction conditions are very mild and functional group-tolerated, such as hydrosilanes, alcohols, phenol, and amino acids. A mechanism is proposed in which the tertiary amine reacts with dimethyl but-2-ynedioate to form zwitterionic salt, and then the zwitterionic intermediate subsequently accept hydrogen to assist the nucleophilic attack of oxygen atom of carboxyl group at the benzyl group of tertiary amine, while a separate reaction pathway leads to esterification. (C) 2012 Elsevier Ltd. All rights reserved.
• p-Bromobenzyl Bromide in the Identification of Some Aromatic Carboxylic Acids
  作者：B. A. Fiekers、E. M. Di Geronimo

  DOI：10.1021/ja01184a504

  日期：1948.4