2-bromobenzyl 4-chlorobenzoate | 1401317-74-5

• 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: 2-bromobenzyl 4-chlorobenzoate
• 英文别名: (2-Bromophenyl)methyl 4-chlorobenzoate；(2-bromophenyl)methyl 4-chlorobenzoate
• CAS: 1401317-74-5
• 化学式: C₁₄H₁₀BrClO₂
• 分子量: 325.589
• InChiKey: ALHDITKWZAOBHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 邻溴苯甲醛 在 {ⁿBuMg[2-(Me₃CNCH₂)C₄H₃N]Na(Et₂O)}_∞ 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以69%的产率得到2-bromobenzyl 4-chlorobenzoate
  参考文献：
  名称：

  碱金属有机镁酸盐络合物作为高化学选择性交叉-季申科反应的催化剂。

  摘要：

  通过与碱金属试剂和二正丁基镁共络合，已合成了五种带有双齿双阴离子吡咯基配体的新型异双金属镁氧酸盐。这些配合物的单晶X射线结构分析显示了多种有趣的键合模式。这些碱金属（Li，Na和K）有机镁酸盐被用作Tishchenko反应与两种不同醛的交叉偶联催化剂。烷基镁钠络合物{nBuMg [2-（Me3CNCH2）C4H3N] Na（Et2O）}∞（3）被鉴定为有效的催化剂，因为它在温和条件下表现出较高的催化活性和化学选择性。

  DOI：

  10.1039/d0dt01114b

文献信息

• The Thiolate-Catalyzed Intermolecular Crossed Tishchenko Reaction: Highly Chemoselective Coupling of Two Different Aromatic Aldehydes
  作者：Simon P. Curran、Stephen J. Connon

  DOI：10.1002/anie.201206343

  日期：2012.10.22

  Crossed products: Ortho‐substituted benzaldehydes react with other aromatic aldehydes in a highly selective, atom‐economical Tishchenko disproportionation (see scheme) in the presence of a readily prepared, inexpensive thiolate‐based catalyst. The methodology is of exceptionally wide scope and exhibits a high functional‐group tolerance.

  交叉产物：在现成的，廉价的基于硫醇盐的催化剂的存在下，邻位取代的苯甲醛与其他芳香族醛类发生高度选择性，原子经济的蒂申科歧化反应（参见方案）。该方法的适用范围非常广泛，并且具有很高的功能组容忍度。
• Sodium organoaluminate containing bidentate pyrrolyl ligand: Synthesis, structure, and catalytic activity for the Tishchenko reaction
  作者：Yu Liu、Zhiqiang Guo、Yakong Wang

  DOI：10.1016/j.jorganchem.2021.121882

  日期：2021.7

  An novel sodium organoaluminate containing bidentate pyrrolyl ligand [C4H3NH(2-CH2NHtBu)] was efficiently synthesized and characterized by X-ray crystallography. The molecular structure shows it is a monodimensional infinite chain structures with linear arrangements. Its basic repeat unit comprises the Al atom bonded to two deprotonated pyrrole rings and Na atom coordinated to of nitrogen atoms of

  高效合成了一种新型的含有双齿吡咯基配体[C 4 H 3 NH（2-CH 2 NH t Bu）]的有机铝酸钠，并通过X射线晶体学对其进行了表征。分子结构表明它是具有线性排列的一维无限链结构。它的基本重复单元包含的铝原子键合至两个去质子化的吡咯环和Na原子配位到-N的氮原子的吨卜片段，其经历进一步的ƞ坐标的相邻分子的吡咯环2 -fasion。此外，该有机铝酸钠对Tishchenko反应表现出高催化活性。
• 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.
• Alkali-metal organomagnesiate complexes as catalysts for highly chemoselective crossed-Tishchenko reactions
  作者：Zhiqiang Guo、Tengfei Pang、Yakong Wang、Yongbin Zhang、Xuehong Wei

  DOI：10.1039/d0dt01114b

  日期：——

  magnesiates bearing bidentate dianionic pyrrolyl ligands have been synthesized through co-complexation with alkali-metal reagents and di-n-butylmagnesium. Single-crystal X-ray structural analysis of these complexes revealed a variety of intriguing bonding modes. These alkali-metal (Li, Na, and K) organomagnesiates were utilized as catalysts for cross-coupling Tishchenko reactions with two different aldehydes

  通过与碱金属试剂和二正丁基镁共络合，已合成了五种带有双齿双阴离子吡咯基配体的新型异双金属镁氧酸盐。这些配合物的单晶X射线结构分析显示了多种有趣的键合模式。这些碱金属（Li，Na和K）有机镁酸盐被用作Tishchenko反应与两种不同醛的交叉偶联催化剂。烷基镁钠络合物nBuMg [2-（Me3CNCH2）C4H3N] Na（Et2O）}∞（3）被鉴定为有效的催化剂，因为它在温和条件下表现出较高的催化活性和化学选择性。