3-pyridin-2-yl-acrylic acid n-butyl ester

• 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-pyridin-2-yl-acrylic acid n-butyl ester
• 英文别名: (E)-butyl 3-(pyridin-2-yl)acrylate；butyl 3-(2-pyridyl)-acrylate；butyl (E)-3-pyridin-2-ylprop-2-enoate
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: PMWMHGCCETXWEL-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吡啶 、 丙烯酸丁酯 在 1,10-菲罗啉 、 氧气 、 silver(I) acetate 、 palladium diacetate 、 三甲基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 140.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 以58%的产率得到3-pyridin-2-yl-acrylic acid n-butyl ester
  参考文献：
  名称：

  钯催化吡啶的C-2选择性CH烯烃化

  摘要：

  已经开发了一种新颖且有效的方案，用于通过钯催化的氧化交叉偶联反应对吡啶进行C-2选择性烯化。广泛的吡啶和烯烃底物（包括丙烯酸酯，苯乙烯和丙烯酰胺）是相容的。该产品是生物活性生物碱天然产物和药物分子合成的高度有用的构建基块。

  DOI：

  10.1002/adsc.201200195

文献信息

• <i>N</i>,<i>N</i>-Dimethyl-β-alanine as an Inexpensive and Efficient Ligand for Palladium-Catalyzed Heck Reaction
  作者：Xin Cui、Zhe Li、Chuan-Zhou Tao、Yu Xu、Juan Li、Lei Liu、Qing-Xiang Guo

  DOI：10.1021/ol060585n

  日期：2006.6.1

  phosphine-free ligand than the previously reported ligand, N,N-dimethylglycine, in the Pd-catalyzed Heck reaction for a variety of aryl bromides, aryl iodides, and activated aryl chlorides with a practical turnover number of 10(3). Both kinetic and theoretical studies suggested that N,N-dimethyl-beta-alanine led to faster oxidative addition of an aryl halide to Pd than N,N-dimethylglycine. [reaction: see text]

  在钯催化的多种芳基溴化物，芳基碘化物和碘化物的Heck反应中，N，N-二甲基-β-丙氨酸是一种比以前报道的配体N，N-二甲基甘氨酸更有效的无膦配体。实际营业额为10（3）的活化的芳基氯化物。动力学和理论研究均表明，N，N-二甲基-β-丙氨酸比N，N-二甲基甘氨酸能更快地将芳基卤化物氧化成Pd。[反应：看文字]
• First Application of Secondary Phosphines as Supporting Ligands for the Palladium-Catalyzed Heck Reaction: Efficient Activation of Aryl Chlorides
  作者：Anita Schnyder、Thomas Aemmer、Adriano F. Indolese、Ulrich Pittelkow、Martin Studer

  DOI：10.1002/1615-4169(200207)344:5<495::aid-adsc495>3.0.co;2-6

  日期：2002.7

  Secondary dialkylphosphines were successfully used for the first time as efficient supporting ligands for the palladium-catalyzed Heck reaction of electron-rich and electron-poor aryl chlorides with olefins such as acrylate, ethylene, styrene, and n-butyl vinyl ether. The yields with HP(t-butyl)2 and HP(adamantyl)2 were comparable or better than those obtained with known systems of tertiary phosphines

  仲二烷基膦首次成功地用作富钯和贫电子芳基氯化物与烯烃（如丙烯酸酯，乙烯，苯乙烯和正丁基乙烯基醚）的钯催化的Heck反应的有效支撑配体。HP（叔丁基）2和HP（金刚烷基）2的产率与已知的叔膦体系如P（环己基）3和P（叔丁基）3的产率相当或更好。，尤其是在催化剂负载＜1mol％的情况下。与叔膦相比，仲膦具有易于以工业规模以低成本获得的优点，并且在处理和氧敏感性方面是可比的。
• Heck reaction with heteroaryl halides in the presence of a palladium-tetraphosphine catalyst
  作者：Florian Berthiol、Marie Feuerstein、Henri Doucet、Maurice Santelli

  DOI：10.1016/s0040-4039(02)01109-7

  日期：2002.8

  cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C3H5)]2 system catalyses efficiently the Heck reaction of heteroaryl halides with n-butyl acrylate, styrene, vinylpyridine and vinyl ether derivatives. High turnover numbers can be obtained for the reactions with halo pyridines, quinolines, furans or thiophenes.

  顺式，顺式，顺式-1,2,3,4-四（二苯基膦甲基）环戊烷/ [PdCl（C3H5）] 2系统有效地催化杂芳基卤化物与丙烯酸正丁酯，苯乙烯，乙烯基吡啶和乙烯基醚衍生物的Heck反应。与卤代吡啶，喹啉，呋喃或噻吩的反应可获得较高的转化率。
• Coupling of nucleophiles, vinyl compounds or CO with water, alcohols or amines to organic compounds
  申请人：Solvias AG

  公开号：EP1132361A1

  公开（公告）日：2001-09-12

  Process for the coupling of a) nucleophiles selected from the group alcohols, thioles, amines, metallised hydrocarbons, CH-acidic compounds and metal cyanides, or of b) carbon monoxide mixed with water, alcohols, ammonia, primary or secondary amines, to organic compounds selected from the group of leaving-group-containing aromatics, hetero-aromatics with a C-bonded leaving group, aromatic or hetero-aromatic methyl compounds with a leaving group bonded to the methyl group, ethylenically unsaturated organic compounds with a C-bonded leaving group, or organic allyl compounds with a leaving group in allyl position, or c) vinyl compounds with leaving-group-containing aromatics, whilst cleaving the leaving group in the presence of Pd complexes with monophospholine ligands as the catalyst, whereby variants b) and c) are carried out in the presence of an inorganic base or organic nitrogen base, the process being characterised in that the Pd complex contains secondary monophosphines with aliphatic, branched or cyclic substituents as ligands.

  耦合工艺 a) 选自醇、硫醇、胺、金属化烃、CH 酸性化合物和金属氰化物组的亲核物，或 b) 与水、醇、氨、伯胺或仲胺混合的一氧化碳，与选自以下组别的有机化合物发生偶联：含离去基团的芳香族化合物、带有 C 键离去基团的杂芳香族化合物、带有与甲基键合的离去基团的芳香族或杂芳香族甲基化合物、带有 C 键离去基团的乙烯基不饱和有机化合物或在烯丙基位置带有离去基团的有机烯丙基化合物，或 c) 含离去基团芳香族的乙烯基化合物、 在具有单磷配体的钯络合物作为催化剂存在的情况下裂解离去基团，其中变体 b) 和 c) 在无机碱或有机氮碱存在的情况下进行，该工艺的特点是钯络合物含有脂肪族、支链或环状取代基作为配体的仲单磷酸。
• Ligand-Promoted C-3 Selective C–H Olefination of Pyridines with Pd Catalysts
  作者：Mengchun Ye、Guo-Lin Gao、Jin-Quan Yu

  DOI：10.1021/ja2021075

  日期：2011.5.11

  Pd-catalyzed C-3 selective olefination of pyridines is developed for the first time using 1,10-phenanthroline as the ligand. This finding provides a novel disconnection for the synthesis of pyridine-containing alkaloids and drug molecules as well as a new approach for developing Pd-catalyzed C H functionalizations of pyridines.