3-(2,2-dimethyl-propinyloxy)-benzoic acid ethyl ester | 918402-92-3

• 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: 3-(2,2-dimethyl-propinyloxy)-benzoic acid ethyl ester
• 英文别名: 3-(2,2-dimethyl-1-oxopropoxy)benzoic acid ethyl ester；ethyl 3-(pivaloyloxy)benzoate；Ethyl 3-[(2,2-dimethylpropanoyl)oxy]benzoate；ethyl 3-(2,2-dimethylpropanoyloxy)benzoate
• CAS: 918402-92-3
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: BDNRNZTYWLZRCM-UHFFFAOYSA-N

物化性质

• 沸点：
  340.1±25.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  3-(2,2-dimethyl-propinyloxy)-benzoic acid ethyl ester 、 5-甲基苯并唑 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium phosphate 、 1,2-双(二环己基磷基)-乙烷 作用下， 以 对二甲苯 为溶剂， 反应 22.0h， 以76%的产率得到ethyl 3-(5-methyl-1,3-benzoxazol-2-yl)benzoate
  参考文献：
  名称：

  苯并恶唑和恶唑的镍催化CH芳基化：表征苯酚亲电子中电子，立体和离去基团变异的影响。

  摘要：

  Electronic, steric and leaving group effects for Ni-catalyzed direct arylations using C-O electrophiles were benchmarked. The scope of arylations with pivalates was general with respect to both the electronics on the electrophile and the azoles. Furthermore, the arylation of azoles with tosylates, mesylates and carbamates with varying electronics was explored, and showed electronic trends similar to those of the pivalate reactions. Finally, the relative rate of arylation of 5-methyl benzoxazole with two electronically-similar electrophiles bearing different leaving groups was established. The results from these studies implicate the following order of relative reactivity: mesylates > pivalates > carbamates. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.02.021
• 作为产物：
  描述：

  3-羟基苯甲酸乙酯 、 三甲基乙酰氯 在 吡啶 作用下， 反应 2.0h， 以90%的产率得到3-(2,2-dimethyl-propinyloxy)-benzoic acid ethyl ester
  参考文献：
  名称：

  Highly Functionalized Benzene Syntheses by Directed Mono or Multiple Magnesiations with TMPMgCl·LiCl

  摘要：

  The direct magnesiation of highly functionalized aromatics bearing an ester, a nitrile, or a ketone can be readily performed by using an OBoc as a directing group and TMPMgCl-LiCl as a base. It allows, for example, the preparation of a meta-magnesiated benzophenone in > 95%. After quenching, highly functionalized and substituted benzenes are obtained.

  DOI：

  10.1021/ol0625536

文献信息

• <scp>Nickel‐Catalyzed Cross‐Coupling</scp> of Aryl Pivalates with Cyclobutanols Involving C—O and C—C Bond Cleavage ^†
  作者：Yi Gan、Ninghui Zhang、Shaoxu Huang、Yuanhong Liu

  DOI：10.1002/cjoc.202000319

  日期：2020.12

  An efficient nickel‐catalyzed cross‐coupling of aryl pivalates with cyclobutanols is described. The use of Ni(cod)2/PCy3/base as the catalytic system enables the cleavage of inert C—O bond and C—C bond under mild conditions, thus providing a facile access to γ‐arylated ketones in generally good to excellent yields. This transformation is also characterized by wide substrate scope and functional group

  描述了一种有效的镍催化新戊酸芳基酯与环丁醇的交叉偶联。通过使用Ni（cod）2 / PCy 3 /碱作为催化体系，可以在温和条件下裂解惰性C-O键和C-C键，从而可以轻松获得γ-芳基化的酮（通常良好或优异）产量。这种转化还具有广泛的底物范围和官能团相容性，例如在反应过程中可以很好地耐受甲氧基，N，N-二甲基氨基，酮基，酯基，氟基和TMS基团。
• Nickel-catalyzed C−H arylation of benzoxazoles and oxazoles: Benchmarking the influence of electronic, steric and leaving group variations in phenolic electrophiles
  作者：Deborah F. Steinberg、Morgan C. Turk、Dipannita Kalyani

  DOI：10.1016/j.tet.2017.02.021

  日期：2017.4

  Electronic, steric and leaving group effects for Ni-catalyzed direct arylations using C-O electrophiles were benchmarked. The scope of arylations with pivalates was general with respect to both the electronics on the electrophile and the azoles. Furthermore, the arylation of azoles with tosylates, mesylates and carbamates with varying electronics was explored, and showed electronic trends similar to those of the pivalate reactions. Finally, the relative rate of arylation of 5-methyl benzoxazole with two electronically-similar electrophiles bearing different leaving groups was established. The results from these studies implicate the following order of relative reactivity: mesylates > pivalates > carbamates. (C) 2017 Elsevier Ltd. All rights reserved.
• Highly Functionalized Benzene Syntheses by Directed Mono or Multiple Magnesiations with TMPMgCl·LiCl
  作者：Wenwei Lin、Oliver Baron、Paul Knochel

  DOI：10.1021/ol0625536

  日期：2006.11.1

  The direct magnesiation of highly functionalized aromatics bearing an ester, a nitrile, or a ketone can be readily performed by using an OBoc as a directing group and TMPMgCl-LiCl as a base. It allows, for example, the preparation of a meta-magnesiated benzophenone in > 95%. After quenching, highly functionalized and substituted benzenes are obtained.