ethyl 3-phenylpyridine-2-carboxylate | 96898-21-4

• 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: ethyl 3-phenylpyridine-2-carboxylate
• CAS: 96898-21-4
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: TZHUEBNTHIPDLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  ethyl 3-phenylpyridine-2-carboxylate 以 四氢呋喃 为溶剂， 生成 3-苯基-2-吡啶甲酸
  参考文献：
  名称：

  WO2023/118434

  摘要：

  公开号：
• 作为产物：
  描述：

  ethyl (E)-3-phenyl-2-[(triphenyl-lambda5-phosphanylidene)amino]prop-2-enoate 、 丙烯醛 以 甲苯 为溶剂， 反应 24.0h， 以53%的产率得到ethyl 3-phenylpyridine-2-carboxylate
  参考文献：
  名称：

  6π-electrocyclization of azahexa-1,3,5-trienes: a new entry to a regiospecific synthesis of 3-aryl(heteroaryl)pyridines

  摘要：

  Aza Wittig reaction of iminophosphoranes derived from ethyl alpha-azido-beta-aryl(pyrazolyl)propenoates with alpha,beta-unsaturated aldehydes leads to aldimines which by heating undergo electrocyclic ring-closure through the 3-azahexa-1,3,5-triene moiety to give 3-aryl(pyrazolyl)pyridines in a completely regiospecific fashion. However, iminophosphoranes derived from ethyl alpha-azido-beta-furyl(thienyl)propenoates furnish a mixture (1.2:1 ratio) of the corresponding furo- or thieno-pyridine(2-azahexa-1,3,5-triene electrocyclization product) and 3-furyl(thienyl)pyridine(3-azahexa-1,3,5-triene electrocyclization product).

  DOI：

  10.1016/s0040-4020(01)87250-1

文献信息

• Inverse electron demand Diels-Alder reactions of heterocyclic azadienes: formal total synthesis of streptonigrin
  作者：Dale L. Boger、James S. Panek

  DOI：10.1021/ja00306a024

  日期：1985.10.1

  Synthese de streptonigrine par 2 cycloadditions successives: tetrazine-1,2,4,5 dicarboxylate de dimethyle et methoxy-6 nitro-5 quinoleinecarbothioimidate-2 de methyle; [methoxy-6 nitro-5 quinolyl-2]-5 triazine-1,2,4 dicarboxylate-3,6 de dimethyle obtenu et [benzyloxy-2 dimethoxy-3,4 phenyl]-1' propenyl-4 morpholine. Ces 2 cycloadditions sont etudiees sur une serie de composes

  合成这些 de streptonigrine par 2 cycloadditions 连续序列: tetrazine-1,2,4,5 dicarboxylate dedimethyle et methoxy-6 nitro-5 quinoleinecarbothioimidate-2 demethyle; [甲氧基-6 硝基-5 quinolyl-2]-5 triazine-1,2,4 dicarboxylate-3,6 dedimethyle obtenu et [benzyloxy-2 dimethoxy-3,4 phenyl]-1' propenyl-4 morpholine。Ces 2 cycloadditions Sont etudiees sur une serie de composes
• Diimidazolium Salt HBDIM: An Easily Available, Low‐Cost, CageCarbene Precursor with Broad Applications in Transition Metal‐Catalyzed Reactions
  作者：Weikang Jiang、Weichen Huang、Meichen Xu、Xuebing Leng、Long Lu、Qilong Shen

  DOI：10.1002/chem.202300991

  日期：2023.7.14

  Two is better than one: Diimidazolium salt HBDIM 1, a precursor for di-NHCs ligand CageCarbene, from cheap and easily available agent hexabenzylhexaazaisowurtzitane (HBIW) was developed. Studies showed that the steric hinderance of CageCarbene is similar to that of SIMes but smaller than that of IPr, and electronically, CageCarbene is a strong σ-donator similar to SIMs and a stronger σ-donator than

  两种优于一种：二咪唑鎓盐 HBDIM 1 是二 NHC 配体 CageCarbene 的前体，由廉价且容易获得的试剂六苄基六氮杂异武兹烷 (HBIW) 开发而成。研究表明，CageCarbene的位阻与SIMes相似，但小于IPr，并且在电子学上，CageCarbene是类似于SIMs的强σ供体，并且比IPr更强的σ供体。合成了含金、铜或钯的笼卡宾双金属配合物2 – 4 ，并对其进行了充分表征，包括其单晶的 X 射线衍射。进一步的研究表明，配合物2 – 4具有高反应性，可催化多达 17 个反应。
• 6π-electrocyclization of azahexa-1,3,5-trienes: a new entry to a regiospecific synthesis of 3-aryl(heteroaryl)pyridines
  作者：Pedro Molina、Aurelia Pastor、Maria Jesús Vilaplana

  DOI：10.1016/s0040-4020(01)87250-1

  日期：1993.8

  Aza Wittig reaction of iminophosphoranes derived from ethyl alpha-azido-beta-aryl(pyrazolyl)propenoates with alpha,beta-unsaturated aldehydes leads to aldimines which by heating undergo electrocyclic ring-closure through the 3-azahexa-1,3,5-triene moiety to give 3-aryl(pyrazolyl)pyridines in a completely regiospecific fashion. However, iminophosphoranes derived from ethyl alpha-azido-beta-furyl(thienyl)propenoates furnish a mixture (1.2:1 ratio) of the corresponding furo- or thieno-pyridine(2-azahexa-1,3,5-triene electrocyclization product) and 3-furyl(thienyl)pyridine(3-azahexa-1,3,5-triene electrocyclization product).
• WO2023/118434
  申请人：——

  公开号：——

  公开（公告）日：——