N-methyl-N-phenyl-4-pyridinecarboxamide | 252930-65-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-methyl-N-phenyl-4-pyridinecarboxamide
• 英文别名: N-methyl-N-phenyl isonicotinamide；N-methyl-N-phenylisonicotinamide；N-Methyl-N-phenyl-isonicotinsaeureamid；N-methyl-N-phenylpyridine-4-carboxamide
• CAS: 252930-65-7
• 化学式: C₁₃H₁₂N₂O
• 分子量: 212.251
• InChiKey: IFYISVHCTQWKJB-UHFFFAOYSA-N

物化性质

• 沸点：
  364.3±24.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 N-methyl-N-phenyl-4-pyridinecarboxamide 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以14%的产率得到2-methyl-8-trifluoromethanesulfonyl-2,8-aza-benzo[c]spiro[4.5]deca-6,9-dien-1-one
  参考文献：
  名称：

  Electrophile-Induced Dearomatizing Spirocyclization of N-Arylisonicotinamides: A Route to Spirocyclic Piperidines

  摘要：

  Treatment of N-arylisonicotinamides with trifluoromethanesulfonic anhydride triggers intramolecular nucleophilic attack of the aryl ring on the 4-position of the pyridinium intermediate. The products are spirocyclic dihydropyridines which can be converted to valuable spirocyclic piperidines related to biologically active molecules such as MK-677.

  DOI：

  10.1021/ol801092s
• 作为产物：
  描述：

  异烟酸 在 吡啶 、 氢氧化钾 、 sodium hydroxide 、 氯化亚砜 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 12.08h， 生成 N-methyl-N-phenyl-4-pyridinecarboxamide
  参考文献：
  名称：

  Synthesis of 2-Pyridinylbenzoxazole:  Mechanism for the Intramolecular Photosubstitution of the Haloarene with the Carbonyl Oxygen of the Amide Bond in Basic Medium

  摘要：

  2-Pyridinylbenzoxazole derivatives have been synthesized by the intramolecular photosubstitution reaction of N-(2-halophenyl)pyridinecarboxamide (1 and 2) with its amide bond in basic medium. In neutral medium both intramolecular photosubstitution and photoreduction reactions occurred. In the photosubstitution reaction a singlet state of the o-haloarene is involved, whereas in the photoreduction a triplet state of the o-haloarene is involved; oxygen inhibited the photoreduction but not the photosubstitution. The relative rate studies showed that a base accelerates the photosubstitution reaction but decelerates the photoreduction. o-Iodoarenecarboxamide is more reactive than o-bromoarenecarboxamide, which in turn is more reacitive than o-chloroarenecarboxamide. UV-vis absorption change in the presence of a base showed that an imidol and/or imidolate anion is involved in the reaction. Several transient species, such as charge-transfer excited states and a cyclohexadienyl anion radical, have been identified from the photolysis of 1 and 2 in basic medium by laser flash photolysis. In neutral medium dibromide anion radical and a phenyl a radical were identified in addition to the above intermediates. On the basis of the photokinetic and laser flash photolysis studies, an intramolecular photosubstitution of N-(o-halophenyl)-pyridinecarboxamide with its amide bond occurs via an intramolecular S-N(ET)Ar* mechanism to afford 2-pyridinylbenzoxazole derivative, and the photoreduction proceeds via a free radical mechanism to give N-phenylpyridinecarboxamide.

  DOI：

  10.1021/jo9909498

文献信息

• Facile amidation of esters with aromatic amines promoted by lanthanide tris (amide) complexes
  作者：Zhao Li、Chenjun Guo、Jue Chen、Yingming Yao、Yunjie Luo

  DOI：10.1002/aoc.5517

  日期：2020.4

  The development of catalysts capable of catalyzing amidation of esters with amines to construct amides under mild conditions is of great importance. Compared to aliphatic amines, the direct catalytic amidation of esters with less nucleophilic aromatic amines is rather difficult. Employing simple lanthanide tris (amide) complexes Ln[N (SiMe3)2]3(μ‐Cl)Li (THF)3 as the catalysts, it was found a broad

  在温和条件下开发能够催化酯与胺酰胺化以构建酰胺的催化剂非常重要。与脂族胺相比，酯与较少亲核芳族胺的直接催化酰胺化相当困难。采用简单的镧系元素三（酰胺）络合物LN [N（森达3）2 ] 3（μ -Cl）的Li（THF）3作为催化剂，已发现宽范围的芳族胺和酯的被有效地转换成以各种酰胺在温和的条件下丰产。从镧系元素三（酰胺）配合物与底物胺之间的酰胺交换反应开始，实验上证实了这种转化的合理机制。
• Electrochemical reductions of pyridine carboxamide bases
  申请人：REILLY INDUSTRIES, INC.

  公开号：EP0189678A1

  公开（公告）日：1986-08-06

  Electrochemical reductions of pyridine carboxamide bases performed by electrolysis in a divided flow cell utilizing an ion-exchange membrane at a high hydrogen-overvoltage cathode and in an aqueous or partly aqueous medium comprising a Lowry-Bronsted acid in at least a 1:1 equivalent ratio with the pyridine carboxamide base. A titanium salt catalyst and other means are disclosed to add selectivity to the reduction and improve yield of the amine or other desired reaction product. With all bases, significant advantages of a commercial and industrial nature are reported over prior art static, beaker cell technology.

  吡啶羧酰胺碱的电化学还原是在分流池中利用离子交换膜在高氢电压阴极和水介质或部分水介质中进行电解进行的，水介质中含有与吡啶羧酰胺碱至少为 1:1 等效比的洛里-布朗斯泰德酸。已公开的钛盐催化剂和其他方法可增加还原的选择性并提高胺或其他所需反应产物的产量。据报道，与现有的静态烧杯池技术相比，所有碱都具有显著的商业和工业优势。
• Yebeutchou, Roger M.; Dalcanale, Enrico, Journal of the American Chemical Society, 2009, vol. 131, p. 2452 - 2453
  作者：Yebeutchou, Roger M.、Dalcanale, Enrico

  DOI：——

  日期：——
• Compounds and Methods of Use Thereof for Treating Tumors
  申请人：Georgetown University

  公开号：US20150344440A1

  公开（公告）日：2015-12-03

  The invention encompasses novel compounds and pharmaceutically acceptable salts thereof and compositions including therapeutically or prophylactically effective amounts of such compounds or pharmaceutically acceptable salts thereof. The invention also encompasses methods for treating or preventing diseases and disorders associated with abnormal cell growth, for example, treating or preventing cancer or tumor growth, which methods include administering to a mammal in need thereof a composition comprising a therapeutically or prophylactically effective amount of a compound of the invention or a pharmaceutically acceptable salt thereof.
• US9695108B2
  申请人：——

  公开号：US9695108B2

  公开（公告）日：2017-07-04