5-ethenyl-3-pyridinecarboxylic acid methyl ester | 38940-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-ethenyl-3-pyridinecarboxylic acid methyl ester
• 英文别名: methyl 5-ethenylpyridine-3-carboxylate；Methyl 5-vinylnicotinate；5-vinyl-nicotinic acid methyl ester；5-Vinyl-nicotinsaeure-methylester；3-Carbomethoxy-5-vinylpyridin
• CAS: 38940-67-9
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: UAVVZJIMFHIEJV-UHFFFAOYSA-N

物化性质

• 沸点：
  255.4±28.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-ethenyl-3-pyridinecarboxylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以66%的产率得到methyl 5-ethylnicotinate
  参考文献：
  名称：

  Total syntheses and antimicrobial activities of pyridine alkaloids from Rubiaceae

  摘要：

  Pyridine alkaloids from Rubiaceae were prepared by palladium-catalyzed cross-coupling reactions of methyl 5-bromonicotinate (6) with various organometallic reagents. Baker's yeast reduction of the ketone 8 gave the levorotatory alcohol (S)-1. On this basis, the naturally occuring alcohol(+)-1 was assigned to be (R)-configurated. The alkaloids 1 and 4 show weak antimicrobial activities.

  DOI：

  10.1007/bf00807174
• 作为产物：
  描述：

  5-溴烟酸甲酯 、 2,6-二叔丁基-4-甲基苯酚 在 四(三苯基膦)钯 、 三丁基乙烯基锡 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以21.4 mg的产率得到5-ethenyl-3-pyridinecarboxylic acid methyl ester
  参考文献：
  名称：

  [EN] NOVEL HISTONE METHYLTRANSFERASE INHIBITORS
  [FR] NOUVEAUX INHIBITEURS D'HISTONE MÉTHYLTRANSFÉRASES

  摘要：

  本发明涉及式(I)定义的新的化合物。这些化合物是七-β-链家族组蛋白甲基转移酶的抑制剂，特别是KMT9的抑制剂。

  公开号：

  WO2021053158A1

文献信息

• 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。
• Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors
  作者：Christoph W Grathwol、Nathalie Wössner、Sören Swyter、Adam C Smith、Enrico Tapavicza、Robert K Hofstetter、Anja Bodtke、Manfred Jung、Andreas Link

  DOI：10.3762/bjoc.15.214

  日期：——

  The use of light as an external trigger to change ligand shape and as a result its bioactivity, allows the probing of pharmacologically relevant systems with spatiotemporal resolution. A hetero-stilbene lead resulting from the screening of a compound that was originally designed as kinase inhibitor served as a starting point for the design of photoswitchable sirtuin inhibitors. Because the original

  使用光作为外部触发器来改变配体形状并因此改变其生物活性，可以以时空分辨率探测药理学相关系统。通过筛选最初设计为激酶抑制剂的化合物而产生的杂二苯乙烯先导化合物，作为光可切换沉默调节蛋白抑制剂设计的起点。由于原始的二苯乙烯类结构具有不利的光化学特性，因此将其改建为杂芳基二氮烯类似物。通过这种分子内偶氮化，分子的形状保持不变，而光开关能力得到提高。正如预期的那样，高度相似的化合物在其热力学稳定的拉伸 ( E ) 形式中表现出相似的活性。该异构体的辐照会引发异构化，形成具有弯曲几何形状的长寿命 ( Z ) 构型，从而导致端到端距离显着缩短。由此产生的亲和力变化旨在实现去乙酰化酶的体外实时光调制。
• Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent
  作者：Mincong Su、Xia Huang、Chuanhu Lei、Jian Jin

  DOI：10.1021/acs.orglett.1c04018

  日期：2022.1.14

  nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used

  已经使用（杂）芳基溴化物和乙酸乙烯酯作为偶联伙伴实现了镍催化的还原交叉偶联。这种温和、适用的方法提供了获得各种乙烯基芳烃、杂芳烃和苯并杂环化合物的可靠途径，这将扩大精细化学品和聚合物前体的化学空间。重要的是，使用了一种可持续溶剂二甲基异山梨醇，从绿色化学的角度来看，这使得该协议更具吸引力。
• [EN] HETEROCYCLIC FXR MODULATORS<br/>[FR] MODULATEURS HÉTÉROCYCLIQUES DE FXR
  申请人：HEPAGENE THERAPEUTICS INC

  公开号：WO2018075207A1

  公开（公告）日：2018-04-26

  The present technology is directed to compounds of formula (I), compositions, and methods related to modulation of FXR. In particular, the present compounds and compositions may be used to treat FXR-mediated disorders and conditions, including, e.g., liver disease, hyperlipidemia, hypercholesteremia, obesity, metabolic syndrome, cardiovascular disease, gastrointestinal disease, and atherosclerosis, and renal disease.

  目前的技术针对公式（I）的化合物、组合物和与调节FXR相关的方法。具体来说，这些化合物和组合物可用于治疗FXR介导的疾病和症状，例如肝病、高脂血症、高胆固醇血症、肥胖、代谢综合征、心血管疾病、胃肠疾病、动脉粥样硬化和肾脏疾病。
• Aza-stilbenes as potent and selective c-RAF inhibitors
  作者：Octerloney McDonald、Karen Lackey、Ronda Davis-Ward、Edgar Wood、Vicente Samano、Patrick Maloney、Felix Deanda、Robert Hunter

  DOI：10.1016/j.bmcl.2006.07.063

  日期：2006.10

  The synthesis of several novel aza-stilbene derivatives was carried out. The compounds were tested for their c-RAF enzyme inhibition. Compound 27 possesses significant potency against c-RAF and demonstrates selectivity over other protein kinases. A hypothesis for the binding mode, activity, and selectivity is proposed. (c) 2006 Elsevier Ltd. All rights reserved.