ethyl 4-(pyrimidin-2-yl)benzoate | 259541-89-4

• 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: ethyl 4-(pyrimidin-2-yl)benzoate
• 英文别名: ethyl 4-pyrimidin-2-ylbenzoate
• CAS: 259541-89-4
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: ZYAYIXIILWJKSN-UHFFFAOYSA-N

物化性质

• 熔点：
  75-76 °C
• 沸点：
  291.4±32.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-(pyrimidin-2-yl)benzoate 在 2-(2'-pyrimidyl)phenylpalladium(II) acetate 、 copper(II) trifluoroacetate 、 calcium bromide 作用下， 以 溶剂黄146 为溶剂， 反应 64.0h， 以79%的产率得到ethyl 3,5-dibromo-4-(pyrimidin-2-yl)benzoate
  参考文献：
  名称：

  Direct synthesis of ortho-dihalogenated arylpyrimidines using calcium halides as halogen sources

  摘要：

  Pyrimidines and their derivatives have been used as important motifs in materials and medicinal chemistry. In this Letter, a wide variety of ortho-dihalogenated arylpyrimidines were synthesized with high yields and functional-group tolerance using calcium halides as crucial halogenating agents and cupric trifluoroacetate as oxidant in the presence of air. The generated dichlorinated products could be further manipulated by stepwise Suzuki-Miyaura reaction to afford a wide range of ortho-functionalized arylpyrimidines amenable to physical and biological evaluations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.061
• 作为产物：
  描述：

  2-氯嘧啶 、 对碘苯甲酸乙酯 在 zinc pivalate 、 氯化钴 、 锌 、 三(2-呋喃基)膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 苯甲腈 、 四氢呋喃 为溶剂， 反应 60.0h， 以81%的产率得到ethyl 4-(pyrimidin-2-yl)benzoate
  参考文献：
  名称：

  钴催化相应杂芳基氯化物制备N-杂环有机锌试剂

  摘要：

  在新戊酸锌和 10% CoCl2 的苄腈溶液中，在 25 °C 下，使用锌粉将各种取代和未取代的 N-杂芳基氯化物转化为相应的有机锌物质。得到的杂芳基锌试剂在 9-48 小时内以 43-98% 的产率获得，并与广泛的亲电子试剂反应，产生功能化的杂芳烃。

  DOI：

  10.1055/a-1534-0624

文献信息

• Palladium-Catalyzed Monoselective Halogenation of CH Bonds: Efficient Access to Halogenated Arylpyrimidines using Calcium Halides
  作者：Bingrui Song、Xiaojian Zheng、Jun Mo、Bin Xu

  DOI：10.1002/adsc.200900778

  日期：2010.2.15

  A wide variety of ortho-halogenated arylpyrimidines were prepared with high monoselectivity and functional-group tolerance by using calcium halides as crucial halogenating agents and cupric trifluoroacetate as oxidant in the presence of air.

  通过在空气中使用卤化钙作为关键的卤化剂和三氟乙酸铜作为氧化剂，制备了具有高单选择性和官能团耐受性的多种邻卤代芳基嘧啶。
• Palladium-Catalyzed Regioselective C-H Bond ortho-Acetoxylation of Arylpyrimidines
  作者：Xiaojian Zheng、Bingrui Song、Bin Xu

  DOI：10.1002/ejoc.201000631

  日期：——

  An efficient and regioselective palladium-catalyzed ortho C-H acetoxylation reaction was developed to afford ortho monoacetoxylated arylpyrimidines in good to excellent yields by using cupric trifluoroacetate as a cocatalyst. A wide variety of oxygenated arylpyrimidines were prepared with high regioselectivity and functional group tolerance.

  通过使用三氟乙酸铜作为助催化剂，开发了一种有效且具有区域选择性的钯催化的邻 CH 乙酰氧基化反应，以良好至极好的产率提供邻位单乙酰氧基化芳基嘧啶。制备了多种具有高区域选择性和官能团耐受性的氧化芳基嘧啶。
• Anthranil: An Aminating Reagent Leading to Bifunctionality for Both C(sp³)−H and C(sp²)−H under Rhodium(III) Catalysis
  作者：Songjie Yu、Guodong Tang、Yingzi Li、Xukai Zhou、Yu Lan、Xingwei Li

  DOI：10.1002/anie.201602224

  日期：2016.7.18

  nitrogenation suffered from simple amidation/amination with limited atom‐economy and is mostly limited to C(sp2)−H substrates. In this work, anthranil was designed as a novel bifunctional aminating reagent for both C(sp2)−H and C(sp3)−H bonds under rhodium(III) catalysis, thus affording a nucleophilic aniline tethered to an electrophilic carbonyl. A tridendate rhodium(III) complex has been isolated as the

  以前的直接CH H氮化反应受简单的酰胺化/胺化作用和原子经济的限制，并且大多限于C（sp 2）-H底物。在这项工作中，将蒽醌设计为在铑（III）催化下同时用于C（sp 2）-H和C（sp 3）-H键的新型双功能胺化试剂，从而提供了拴接到亲电羰基的亲核苯胺。已经分离出三登酸盐铑（III）配合物作为催化剂的静止状态，DFT研究确定了亚硝基物质的中间体。
• Exploiting Coordination Effects for the Regioselective Zincation of Diazines Using TMPZnX⋅LiX (X=Cl, Br)
  作者：Alexander Kremsmair、Alisa S. Sunagatullina、Leonie J. Bole、Pasquale Mastropierro、Simon Graßl、Henrik R. Wilke、Edouard Godineau、Eva Hevia、Paul Knochel

  DOI：10.1002/anie.202210491

  日期：2022.10.4

  N-heterocycles such as pyrimidines were regioselectively zincated using bimetallic bases of type TMPZnX⋅LiX (TMP=2,2,6,6-tetramethylpiperidyl; X=Cl, Br) and subsequently quenched with electrophiles. Trapping of key organometallic intermediates has shed light on their complex solution constitution and helped to explain the high regioselectivity observed as well as the stoichiometry of the base used.

  使用 TMPZnX·LiX 型双金属碱（TMP=2,2,6,6-四甲基哌啶基；X=Cl，Br）对重要的N杂环（例如嘧啶）进行区域选择性锌化，然后用亲电子试剂淬灭。关键有机金属中间体的捕获揭示了它们复杂的溶液组成，并有助于解释观察到的高区域选择性以及所用碱的化学计量。
• Cobalt-Catalyzed Cross-Coupling Between In Situ Prepared Arylzinc Halides and 2-Chloropyrimidine or 2-Chloropyrazine
  作者：Jeanne-Marie Bégouin、Corinne Gosmini

  DOI：10.1021/jo900240d

  日期：2009.4.17

  A cobalt-catalyzed cross-coupling of aryl halides with 2-chloropyrimidines or 2-chloropyrazines is reported in satisfactory to high yields. The key step of this procedure is the formation of aromatic organozinc reagents and their coupling with 2-chlorodiazines using the same cobalt halide as catalyst and Zn dust under mild reaction conditions. This new cobalt-catalyzed coupling reaction represents a practical and interesting alternative to previously known methods for the synthesis of 2-aryldiazines.