3-(3'-pyridinyl)-(Z)-propenoic acid methyl ester | 228271-59-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(3'-pyridinyl)-(Z)-propenoic acid methyl ester
• 英文别名: (Z)-methyl 3-(pyridin-3-yl)acrylate；methyl (Z)-3-(3'-pyridyl)acrylate；methyl(Z)-3-(3'-pyridyl) acrylate；(Z)-methyl 3-(3-pyridyl)acrylate；Methyl(Z)-3-(pyridin-3-yl)acrylate；methyl (Z)-3-pyridin-3-ylprop-2-enoate
• CAS: 228271-59-8
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: APCQGKVIYRVRKN-PLNGDYQASA-N

物化性质

• 沸点：
  269.8±15.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：

  3-(3'-pyridinyl)-(Z)-propenoic acid methyl ester 在 氯化亚砜 、 二异丁基氢化铝 作用下， 以 正己烷 、 氯仿 、 水 、 甲苯 为溶剂， 反应 9.5h， 生成 Methyl-propyl-((Z)-3-pyridin-3-yl-allyl)-amine
  参考文献：
  名称：

  Synthesis and binding of 6,7,8,9-tetrahydro-5H-pyrido[3,4-d]azepine and related ring-opened analogs at central nicotinic receptors

  摘要：

  6,7,8,9-Tetrahydro-5H-pyrido[3,4-d]azepine (5a) and its N-7-methyl derivative 5b were synthesized and evaluated as potential nicotinic acetylcholinergic receptor (nAChR) ligands. On the basis that 6,7,8,9-tetrahydro-5H-pyrido[3,4-c]azepine (4a), which binds at nAChRs with low affinity (K-i = 1100 nM), possesses an internitrogen distance (4.6 Angstrom) that may be less than optimal, we designed compound 5a due to its similar shape but longer internitrogen distance (5.5 Angstrom). Compound 5a (K-i = 45 nM) was found to bind with enhanced affinity. However, unlike what is seen with nornicotine/nicotine, N-methylation of 5a reduced affinity (5b; K-i = 268 nM) rather than enhancing it. The results suggest that 5 may interact at nicotine receptors in a manner that is somewhat different from that of nicotine. Ring-opening of the pyrido[3,4-d]azepine ring led to a series of 3-(2-aminoethyl)pyridines 21 that retained the affinity of the cyclic compound. Subsequent modification, including further chain lengthening (e.g. aminopropylpyridines 22) and introduction of unsaturation, ultimately led to the development of a series of 3-(2-aminethoxy)pyridines 27. Simple N-substituted derivatives of 27 were found to bind with K-i values of 20 to 35 nM. Because parallel structural changes in several series of related compounds did not result in parallel shifts in nAChR affinity, it is unlikely that all the investigated compounds bind in a similar fashion at these receptors. Nevertheless, some of these compounds represent novel classes of nAChR ligands. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80051-8
• 作为产物：
  描述：

  3-吡啶甲醛 、 O,O'-双(2,2,2-三氟乙基)磷乙酸甲酯 在 三(3,6-二氧杂庚基)胺 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 以93%的产率得到3-(3'-pyridinyl)-(Z)-propenoic acid methyl ester
  参考文献：
  名称：

  Horner-Wadsworth-Emmons烯烃Z选择性合成不饱和酯的新有效条件

  摘要：

  研究了1（Still试剂）和2（Ando试剂）与醛的Horner-Wadsworth-Emmons反应。当在-78°C下于THF中进行反应时，三[2-（2-甲氧基乙氧基）乙基]胺（TDA-1）被证明是有效的添加剂。1与芳族醛的缩合反应得到的选择性接近95％。已经报道了在该反应中使用5倍过量的18C6。但是，我们定义了仅需要催化量的条件。

  DOI：

  10.1016/j.tetlet.2004.05.026

文献信息

• Wittig Reactions in Water Media Employing Stabilized Ylides with Aldehydes. Synthesis of α,β-Unsaturated Esters from Mixing Aldehydes, α-Bromoesters, and Ph₃P in Aqueous NaHCO₃
  作者：Amer El-Batta、Changchun Jiang、Wen Zhao、Robert Anness、Andrew L. Cooksy、Mikael Bergdahl

  DOI：10.1021/jo070665k

  日期：2007.7.1

  range of stabilized ylides and aldehydes. Despite sometimes poor solubility of the reactants, good chemical yields normally ranging from 80 to 98% and high E-selectivities (up to 99%) are achieved, and the rate of the reactions in water is unexpectedly accelerated. The efficiency of water as a medium in the Wittig reaction is compared to conventional organic solvents ranging from carbon tetrachloride

  事实证明，水是在多种稳定的乙炔和醛上进行维蒂希反应的有效介质。尽管有时反应物的溶解度较差，但通常可获得80-98 ％的良好化学收率和较高的E选择性（高达99％），并且在水中的反应速度出乎意料地加快了。将水作为Wittig反应介质的效率与常规有机溶剂（从四氯化碳到甲醇）进行了比较。当存在大量疏水性实体（例如芳香族，杂环芳香族甲醛和长链脂族醛与三苯基膦）时，维蒂希水溶液反应最有效。该Ë / ž维蒂希产物的β-异构体比例取决于电子接受/给体能力和存在于芳环中的取代基的位置。研究了添加剂（例如苯甲酸，LiCl和十二烷基硫酸钠（SDS））对Wittig反应的影响。Wittig反应也可以在酸性实体例如苯酚和羧酸的存在下进行。另外，脂族醛中的大α-取代基不会危害反应。还证明了醛的水合物可以直接在含水维蒂希反应中用作底物。Wittig水溶液的反应范围扩展到Ph 3的一锅混合物的24个例子碳酸氢钠溶液中的P
• Zur Stereochemie der 3-Oxo-5-phenyl-1-cyclopentancarbonsäuren, 11. Mitt. Synthese der stereomeren 3-Oxo-5-(2,3,4-pyridyl)-cyclopentancarbonsäuren
  作者：Martin Beck、August W. Frahm

  DOI：10.1002/ardp.19863190413

  日期：——

  Es wird die stereoselektive Synthese der 3‐Oxo‐5‐pyridyl‐cyclopentancarbonsäuren 4a–c durch kombinierte Michael‐ und Dieckmannreaktion aus Ethantricarbonsäuretrimethylester und den Azazimtsäuremethylestern 1a‐c beschrieben. Der saure Abbau der 3‐Oxo‐5‐pyridyl‐cyclopentan‐1.1.t‐4‐tricarbonsäuretrimethylester 2a−c führt stereoselektiv zu den cis‐Säuren 4a−c. Nach thermo‐dynamisch gesteuerter Epimerisierung

  描述了通过三甲基乙烷三羧酸酯和甲基氮杂肉桂酸酯 1a-c 的 Michael 和 Dieckmann 反应的立体选择性合成 3-氧代-5-吡啶基-环戊烷羧酸 4a-c。3-氧代-5-吡啶基-环戊烷-1.1.t-4-三羧酸三甲酯2a-c的酸性降解立体选择性地导致顺式酸4a-c。在热力学控制差向异构化后，可以通过柱色谱分离过程分离少量相应的反式酸 3a 和 3b。
• Direct Stereodivergent Olefination of Carbonyl Compounds with Sulfur Ylides
  作者：Jérémy Merad、Phillip S. Grant、Tobias Stopka、Juliette Sabbatani、Ricardo Meyrelles、Alexander Preinfalk、Ján Matyasovsky、Boris Maryasin、Leticia González、Nuno Maulide

  DOI：10.1021/jacs.2c05637

  日期：2022.7.13

  The reactivity of phosphorus and sulfur ylides toward carbonyl compounds constitutes a well-known dichotomy that is a common educational device in organic chemistry─the former gives olefins, while the latter gives epoxides. Herein, we report a stereodivergent carbonyl olefination that challenges this dichotomy, showcasing thiouronium ylides as valuable olefination reagents. With this method, aldehydes

  磷叶立德和硫叶立德对羰基化合物的反应性构成了一个众所周知的二分法，这是有机化学中的一种常见教育手段——前者产生烯烃，而后者产生环氧化物。在此，我们报告了一种挑战这种二分法的立体发散羰基烯化，展示了硫脲叶立德作为有价值的烯化试剂。通过这种方法，醛被转化为具有高立体选择性和广泛底物范围的Z-烯烃，而N-甲苯磺酰亚胺提供了类似的熟练进入E-烯烃的方法。深入的计算和实验研究阐明了这种异常反应的机制细节。
• Osmium-Promoted Dipolar Cycloadditions with Pyrroles: An Efficient, Stereoselective Synthesis of 7-Azanorbornanes
  作者：Javier Gonzalez、Jason I. Koontz、L. Mark Hodges、Kent R. Nilsson、Linda K. Neely、William H. Myers、Michal Sabat、W. Dean Harman

  DOI：10.1021/ja00117a010

  日期：1995.3

  A series of 7-azabicyclo[2.2.1]hept-5-ene complexes are prepared from [Os(NH3)5(eta(2)-L)](2+) (L = pyrrole, 1-methylpyrrole 2,5-dimethylpyrrole. 1,2,5-trimethylpyrrole, or l-(trimethylsilyl)pyrrole) and various dipolarophiles (e.g., acrylonitrile, methyl acrylate, alpha-methylene-gamma-butyrolactone, dimethyl maleate, dimethyl fumarate, N-phenyl maleimide, cyclopentene-1,2-dicarboxylic acid anhydride and (E)- and (Z)- methyl 3-(3'-pyridyl)acrylate). The cycloaddition is promoted by coordination of the pyrrole with [Os(NH3)(5)](2+) across C3 and C4, transforming the uncoordinated portion of the pyrrole nucleus into an azomethine ylide capable of undergoing 1,3-dipolar cycloadditions. The metal serves not only to activate the pyrrole ring but also to stabilize the resulting 7-azabicyclo[2.2.1] heptene ligands. A number of organic 7-azabicyclo[2.2.1]heptanes, including analogs of the alkaloid epibatidine, have been synthesized by this methodology. For the cases examined, the cycloaddition favors exo stereochemistry of the electron-withdrawing substituent when the pyrrole nitrogen is unsubstituted. Crystal structures have been determined for the complexes obtained from the reactions of pyrrole with N-phenylmaleimide (8a), 2,5-dimethylpyrrole with dimethyl maleate (13a), and 2,5-dimethylpyrrole with alpha-methylene-gamma-butyrolactone (22a).
• [EN] MULTICYCLIC COMPOUNDS AND METHODS OF USING SAME<br/>[FR] COMPOSÉS MULTICYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：KARYOPHARM THERAPEUTICS INC

  公开号：WO2015042414A8

  公开（公告）日：2015-08-06