ethyl 3-(2-bromophenyl)propiolate | 1226508-51-5

• 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: ethyl 3-(2-bromophenyl)propiolate
• 英文别名: ethyl o-(bromophenyl)propiolate；Ethyl 3-(2-bromophenyl)prop-2-ynoate
• CAS: 1226508-51-5
• 化学式: C₁₁H₉BrO₂
• 分子量: 253.095
• InChiKey: LFQVEHKQYFHROS-UHFFFAOYSA-N

物化性质

• 沸点：
  320.2±25.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2-bromophenyl)propiolate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 以119 mg的产率得到3-(2-bromophenyl)propiolic acid
  参考文献：
  名称：

  Structural design and synthesis of arylalkynyl amide-type peroxisome proliferator-activated receptor γ (PPARγ)-selective antagonists based on the helix12-folding inhibition hypothesis

  摘要：

  Peroxisome proliferator-activated receptor gamma (PPAR gamma) antagonists are candidates for treatment of type 2 diabetes, obesity and osteoporosis. However, few rational design strategies are currently available. Here, we utilized the helix12 (H12)-folding inhibition hypothesis, in combination with our previously determined X-ray crystal structure of PPAR gamma agonist MEKT-21 (6) complexed with the PPAR gamma ligand-binding domain, to design and develop a potent phenylalkynyl amide-type PPAR gamma antagonist 9i, focusing initially on pinpoint structural modification of the propanoic acid moiety of 6. Since 9i retained very weak, but distinct, PPAR gamma agonist activity, we next modified the distal benzene ring of 9i, aiming to delete the residual PPAR gamma agonist activity while retaining the antagonist activity. Introduction of a chlorine atom at the 2-position of the distal benzene ring afforded 9p, which exhibited potent, PPAR gamma-selective full antagonist activity without detectable agonist activity. We found that 9p stabilized the corepressor PPAR gamma complex and suppressed basal PPAR gamma activity. This compound showed anti-adipogenesis activity at the cellular level. This agonist antagonist switching concept based on the H12-folding inhibition hypothesis should also be applicable for designing other classes of PPAR gamma full antagonists. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.017
• 作为产物：
  描述：

  (2-溴苯乙炔基)三甲基硅烷 在 甲醇 、 正丁基锂 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 ethyl 3-(2-bromophenyl)propiolate
  参考文献：
  名称：

  通过有机催化[2,3]-σ重排对映选择性合成β-氟-β-芳基-α-氨基戊烯酰胺

  摘要：

  加入苄胺后，带有（Z）-3-氟-3-芳基丙-2-烯基的季铵盐的四咪唑促进的催化对映选择性[2,3]-σ重排，产生了一系列的β-氟代-含有立体生成的叔氟取代基的β-芳基-α-氨基戊烯酰胺。容许环状和无环氮取代基以及各种芳族取代基，从而以高达76％的收率，96：4 dr和98：2 er的产率提供β-氟-β-芳基-α-氨基戊烯酰胺产品。

  DOI：

  10.1021/acs.orglett.7b02452

文献信息

• Highly Efficient Copper-Catalyzed Synthesis of Internal Alkynes<i>via</i>Aerobic Oxidative Arylation of Terminal Alkynes
  作者：Honghua Rao、Hua Fu、Yuyang Jiang、Yufen Zhao

  DOI：10.1002/adsc.200900723

  日期：2010.2.15

  We have developed a novel and highly efficient, copper-catalyzed synthesis of internal alkynes via oxidative couplings of aromatic boronic acids with terminal alkynes at room temperature. The protocol uses inexpensive copper(I) oxide [Cu2O] as the catalyst, oxygen in the air as the stoichiometric oxidant; no ligand and sealed reaction vessels are required, and remarkable functional group tolerability

  我们已经开发出一种新型的，高效的铜催化内炔烃，它是在室温下通过芳族硼酸与末端炔烃的氧化偶联而制得的。该协议使用廉价的氧化铜（I）[Cu 2 O]作为催化剂，使用空气中的氧气作为化学计量的氧化剂；不需要配体和密封的反应容器，观察到显着的官能团耐受性并发生偶联。
• Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of Unsymmetrical α,ω-Diynes with Acenaphthylene
  作者：Yukimasa Aida、Yu Shibata、Ken Tanaka

  DOI：10.1021/acs.joc.7b03042

  日期：2018.3.2

  It has been established that a cationic rhodium(I)/(R)-BINAP complex catalyzes the asymmetric [2 + 2 + 2] cycloaddition of unsymmetrical α,ω-diynes with acenaphthylene at room temperature to give the corresponding chiral multicyclic compounds with high yields and ee values. Interestingly, enantioselectivity highly depended on the structures of α,ω-diynes used. The structural requirements of α,ω-diynes

  现已确定，阳离子铑（I）/（R）-BINAP配合物在室温下催化不对称的α，ω-二炔与a烯的不对称[2 + 2 + 2]环加成反应，得到相应的手性多环化合物产量和ee值。有趣的是，对映选择性高度取决于所用的α，ω-二炔结构。高对映体选择性的α，ω-二炔的结构要求与我们先前报道的阳离子铑（I）/（R）-Difluorphos络合物催化的α，ω-二炔的不对称[2 + 2 + 2]环加成反应相反。茚。
• Silver-catalyzed highly efficient synthesis of pyrido[1,2-a]pyrimidin-4-ones from 2-aminopyridines and alkynoates
  作者：Zhengwang Chen、Yuelu Wen、Hao Ding、Guotian Luo、Min Ye、Liangxian Liu、Jun Xue

  DOI：10.1016/j.tetlet.2016.11.079

  日期：2017.1

  heterocycles due to their wide range of bioactivities. An efficient silver-catalyzed intermolecular cyclization of 2-aminopyridines with various alkynoates has been developed. 2-Substituted 4H-pyrido[1,2-a]pyrimidin-4-ones containing a wide range of functional groups are synthesized in the standard conditions. This transformation is conducted under convenient conditions and affords products in good yields

  嘧啶酮由于其广泛的生物活性而成为重要的含氮杂环之一。已经开发了有效的银催化的2-氨基吡啶与各种链烷酸酯的分子间环化。在标准条件下合成含有2-官能取代的4 H-吡啶并[1,2 - a ]嘧啶-4-酮。该转化是在方便的条件下进行的，并以高收率提供产物。
• Regioselective synthesis of oxazole derivatives via palladium-catalyzed and copper-mediated cascade oxidative cyclization
  作者：Jia Zheng、Min Zhang、Liangbin Huang、Xiaohan Hu、Wanqing Wu、Huawen Huang、Huangfeng Jiang

  DOI：10.1039/c3cc49788g

  日期：——

  A novel Pd-catalyzed/Cu-mediated oxidative cyclization has been developed for the synthesis of trisubstituted oxazoles, which is thought to proceed through cascade formation of C-N and C-O bonds. In this protocol, four hydrogen atoms were removed and water was used as the oxygen atom source.

  已开发出新颖的Pd催化/ Cu介导的氧化环化反应来合成三取代的恶唑，据认为该过程可通过CN和CO键的级联形成来进行。在该协议中，除去了四个氢原子，并将水用作氧原子源。
• Palladium‐Catalyzed Regio‐ and Stereoselective Sulfonylation of Aryl Propiolates with Sulfonyl Hydrazides: Access to ( <i>E</i> )‐ <i>β</i> ‐Aryl Sulfonyl Acrylates
  作者：Huanfeng Jiang、Wuxin Yan、Jiuzhong Huang、Chaowei Tan、Lingzhi Zhan、Wanqing Wu

  DOI：10.1002/adsc.201900456

  日期：2019.10.8

  An efficient method for the synthesis of (E)‐β‐aryl sulfonyl acrylates has been reported. This palladium‐catalyzed approach showed excellent regio‐ and stereoselectivity in the sulfonylation of aryl propiolates with sulfonyl hydrazides. Through this approach, a wide range of (E)‐β‐aryl sulfonyl acrylates were obtained in moderate to high yields.

  已经报道了一种合成（E）-β-芳基磺酰基丙烯酸酯的有效方法。这种钯催化的方法在丙酸芳基酯与磺酰肼的磺酰化反应中表现出出色的区域选择性和立体选择性。通过这种方法，可以以中等到高收率获得各种丙烯酸（E）-β-芳基磺酰基丙烯酸酯。