2-乙烯基-苯甲酸甲酯 | 27326-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-乙烯基-苯甲酸甲酯
• 英文名称: methyl o-vinylbenzoate
• 英文别名: methyl 2-vinylbenzoate；methyl 2-ethenylbenzoate；o-Vinylbenzoesaeure-methylester
• CAS: 27326-44-9
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: MPHUYCIKFIKENX-UHFFFAOYSA-N

物化性质

• 沸点：
  253.0±19.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20℃，采用惰性气体保存方式。

反应信息

• 作为反应物：
  描述：

  2-乙烯基-苯甲酸甲酯 在 potassium trimethylsilonate 、 氯甲酸甲酯 作用下， 以 乙醚 为溶剂， 反应 20.0h， 生成 o-Ethenyl-α-diazoacetophenone
  参考文献：
  名称：

  A comparative study of the decomposition of o-alkynyl-substituted aryl diazo ketones. Synthesis of polysubstituted .beta.-naphthols via arylketene intermediates

  摘要：

  The photochemical, thermal, and rhodium-catalyzed decomposition reactions of several closely related o-alkynyl or o-alkenyl alpha-diazoaceto- and propiophenone derivatives have been studied. The reaction outcome is markedly dependent upon the reaction conditions employed for nitrogen extrusion. Thermolysis or photolysis of o-alkynyl alpha-diazopropiophenone derivatives yields polysubstituted beta-naphthols. These products are derived from Wolff rearrangement of the initially formed carbene to give an aryl ketene which undergoes intramolecular cyclization onto the o-alkynyl substituent. In direct contrast to the thermal and photochemical results, Rh(II)-catalyzed decomposition yields products derived from direct attack of a rhodium carbenoid onto the tethered pi-system producing a vinyl carbenoid intermediate. Further reaction of the cyclized carbenoid with the starting diazo compound furnishes a vinyl indenone which undergoes a rapid intramolecular Diels-Alder reaction to produce a novel dimer whose structure was elucidated by an X-ray crystal analysis. Replacement of the methyl group on the diazo center with a sterically less demanding hydrogen atom was also found to play an important role in controlling the outcome of the Rh(II)-catalyzed reaction.

  DOI：

  10.1021/jo00075a045
• 作为产物：
  描述：

  邻甲基苯甲酸甲酯 在 溴 、 silver nitrate 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 水 为溶剂， 生成 2-乙烯基-苯甲酸甲酯
  参考文献：
  名称：

  Rao, A. V. Rama; Reddy, D. Reddeppa; Rao, B. Venkateswara, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1065 - 1066

  摘要：

  DOI：

文献信息

• [EN] METHYL OXAZOLE OREXIN RECEPTOR ANTAGONISTS<br/>[FR] MÉTHYLOXAZOLES ANTAGONISTES DU RÉCEPTEUR DE L'OREXINE
  申请人：MERCK SHARP & DOHME

  公开号：WO2016089721A1

  公开（公告）日：2016-06-09

  The present invention is directed to methyl oxazole compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.

  本发明涉及甲基噁唑化合物，其为促进睡眠的受体拮抗剂。本发明还涉及所述化合物在潜在治疗或预防涉及促进睡眠的神经和精神疾病和疾病中的用途。本发明还涉及包含这些化合物的组合物。本发明还涉及这些组合物在潜在预防或治疗涉及促进睡眠的疾病中的用途。
• Pd-Catalyzed Vinylation of Aryl Halides with Inexpensive Organosilicon Reagents Under Mild Conditions
  作者：Chu-Ting Yang、Jun Han、Jun Liu、Yi Li、Fan Zhang、Hai-Zhu Yu、Sheng Hu、Xiaolin Wang

  DOI：10.1002/chem.201802573

  日期：2018.7.20

  Pd‐catalyzed Hiyama vinylation reaction of non‐activated aryl chlorides and bromides under mild conditions was developed. The use of efficient vinyl donors and electron‐rich sterically hindered phosphine ligands was critical for the success of the reaction. The products of this transformation can be used for Am/Cm separation, an important challenge in nuclear fuel reprocessing. The substituent effect

  在温和条件下开发了钯催化未活化的芳基氯和溴化物的Hiyama乙烯基化反应。有效的乙烯基供体和富含电子的位阻膦配体的使用对于反应成功至关重要。这种转化的产物可用于Am / Cm分离，这是核燃料后处理中的一项重要挑战。还获得了取代基对Am / Cm分离选择性的影响，这可能有助于开发用于分离Am和Cm的新型色谱材料。
• <i>cis</i>-Specific Hydrofluorination of Alkenylarenes under Palladium Catalysis through an Ionic Pathway
  作者：Enrico Emer、Lukas Pfeifer、John M. Brown、Véronique Gouverneur

  DOI：10.1002/anie.201310056

  日期：2014.4.14

  paper describes the hydrofluorination of alkenes through sequential H− and F+ addition under palladium catalysis. The reaction is cis specific, thus providing access to benzylic fluorides. The mechanism of this reaction involves an ionic pathway and is distinct from known hydrofluorinations involving radical intermediates. The first catalytic enantioselective hydrofluorination is also disclosed.

  本文描述了通过连续的^ h烯烃的氢氟化-和F +除了在钯催化下。该反应是顺式 特异性的，因此提供了获得苄基氟化物的途径。该反应的机理涉及离子途径，并且与涉及自由基中间体的已知氢氟化反应不同。还公开了第一催化对映选择性氢氟化。
• Investigation of the structural requirements for N-methyl-D-aspartate receptor positive and negative allosteric modulators based on 2-naphthoic acid
  作者：Mark W. Irvine、Guangyu Fang、Kiran Sapkota、Erica S. Burnell、Arturas Volianskis、Blaise M. Costa、Georgia Culley、Graham L. Collingridge、Daniel T. Monaghan、David E. Jane

  DOI：10.1016/j.ejmech.2018.12.054

  日期：2019.2

  a series of styryl substituted compounds with partial NAM activity and a preference for inhibition of GluN2D versus the other GluN2 subunits. In particular, the 3-and 2-nitrostyryl derivatives UBP783 (79i) and UBP792 (79h) had IC50s of 1.4 μM and 2.9 μM, respectively, for inhibition of GluN2D but showed only 70-80% maximal inhibition. GluN2D has been shown to play a role in excessive pain transmission

  N-甲基-D-天冬氨酸受体 (NMDAR) 是一种由 L-谷氨酸和甘氨酸激活的配体门控离子通道，在学习和记忆的突触可塑性中起主要作用。NMDAR 与阿尔茨海默病和帕金森病等神经退行性疾病有关，而 NMDAR 功能减退与精神分裂症有关。在这里，我们描述了对 2-萘甲酸衍生物的构效关系 (SAR) 研究，以研究 NMDAR 正向和负向变构调节的结构要求。这些研 14b 及其衍生物是研究突触功能的有用工具，并有可能成为开发治疗精神分裂症和导致认知功能丧失的疾病的药物的线索。此外，SAR 研究已经确定了一系列具有部分 NAM 活性的苯乙烯基取代化合物，并且相对于其他 GluN2 亚基更倾向于抑制 GluN2D。特别是，3-和 2-硝基苯乙烯基衍生物 UBP783 (79i) 和 UBP792 (79h) 抑制 GluN2D 的 IC50 值分别为 1.4 μM 和 2.9 μM，但最大抑制作用仅为
• Silver‐Enabled General Radical Difluoromethylation Reaction with TMSCF ₂ H
  作者：Jun Yang、Shengqing Zhu、Fang Wang、Feng‐Ling Qing、Lingling Chu

  DOI：10.1002/anie.202014587

  日期：2021.2.19

  A silver‐mediated oxidative difluoromethylation of styrenes and vinyl trifluoroborates with TMSCF2H is reported for the first time. This method enables direct and facile access to CF2H‐alkenes from abundant alkenes with excellent functional‐group compatibility. Moreover, this Ag/TMSCF2H protocol could further enable a series of radical difluoromethylation reactions of a wide array of substrates, offering

  首次报道了用TMSCF 2 H对苯乙烯和三氟硼酸乙烯基酯进行银介导的氧化二氟甲基化。这种方法可以从丰富的烯烃中直接和轻松地获得CF 2 H-烯烃，并且具有出色的官能团相容性。此外，该Ag / TMSCF 2 H方案可以进一步实现一系列底物的一系列自由基二氟甲基化反应，从而为构建多样化的C-CF 2 H键提供通用和互补的平台。