2-异氰酸基-6-甲基吡啶 | 57310-22-2

• 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
• 中文名称: 2-异氰酸基-6-甲基吡啶
• 英文名称: 2-isocyanato-6-methylpyridine
• 英文别名: 2-Isocyanato-6-methyl-pyridin
• CAS: 57310-22-2
• 化学式: C₇H₆N₂O
• 分子量: 134.137
• InChiKey: ICMAYJUUBLFNDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-异氰酸基-6-甲基吡啶 在 盐酸 、 水 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 27.0h， 生成 1-(2,6-dioxo-1,2,3,4,6,10b-hexahydropyrido[2,1-a]isoindol-10-yl)-3-(6-methylpyridin-2-yl)urea
  参考文献：
  名称：

  Advances in tetrahydropyrido[1,2- a ]isoindolone (valmerins) series: Potent glycogen synthase kinase 3 and cyclin dependent kinase 5 inhibitors

  摘要：

  An efficient synthetic strategy was developed to modulate the structure of the tetrahydropyridine iso-indolone (Valmerin) skeleton. A library of more than 30 novel final structures was generated. Biological activities on CDK5 and GSM as well as cellular effects on cancer cell lines were measured for each novel compound. Additionally docking studies were performed to support medicinal chemistry efforts. A strong GSK3/CDK5 dual inhibitor (38, IC50 GSK3/CDK5 32/84 nM) was obtained. A set of highly selective GSK3 inhibitors was synthesized by fine-tuning structural modifications (29 IC50 GSK3/CDK5 32/320 nM). Antiproliferative effects on cells were correlated with the in vitro Kinase activities and the best effects were obtained with lung and colon cell lines. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.046
• 作为产物：
  描述：

  6-甲基-2-吡啶甲酸 在 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.08h， 生成 2-异氰酸基-6-甲基吡啶
  参考文献：
  名称：

  Advances in tetrahydropyrido[1,2- a ]isoindolone (valmerins) series: Potent glycogen synthase kinase 3 and cyclin dependent kinase 5 inhibitors

  摘要：

  An efficient synthetic strategy was developed to modulate the structure of the tetrahydropyridine iso-indolone (Valmerin) skeleton. A library of more than 30 novel final structures was generated. Biological activities on CDK5 and GSM as well as cellular effects on cancer cell lines were measured for each novel compound. Additionally docking studies were performed to support medicinal chemistry efforts. A strong GSK3/CDK5 dual inhibitor (38, IC50 GSK3/CDK5 32/84 nM) was obtained. A set of highly selective GSK3 inhibitors was synthesized by fine-tuning structural modifications (29 IC50 GSK3/CDK5 32/320 nM). Antiproliferative effects on cells were correlated with the in vitro Kinase activities and the best effects were obtained with lung and colon cell lines. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.046

文献信息

• Electrochemical Synthesis of Imidazo-Fused N-Heteroaromatic Compounds through a C−N Bond-Forming Radical Cascade
  作者：Zhong-Wei Hou、Zhong-Yi Mao、Yared Yohannes Melcamu、Xin Lu、Hai-Chao Xu

  DOI：10.1002/anie.201711876

  日期：2018.2.5

  We have developed a unified strategy for preparing a variety of imidazo‐fused N‐heteroaromatic compounds through regiospecific electrochemical (3+2) annulation reaction of heteroarylamines with tethered internal alkynes. The electrosynthesis employs a novel tetraarylhydrazine as the catalyst, has a broad substrate scope, and obviates the need for transition‐metal catalysts and oxidizing reagents.

  我们已开发出一种通过杂芳基胺与束缚的内部炔烃的区域特异性电化学（3 + 2）环化反应制备各种咪唑并合的N-杂芳族化合物的统一策略。电合成采用新型的四芳基肼作为催化剂，具有广泛的底物范围，并且不需要过渡金属催化剂和氧化剂。
• A diastereoselective approach to axially chiral biaryls via electrochemically enabled cyclization cascade
  作者：Hong Yan、Zhong-Yi Mao、Zhong-Wei Hou、Jinshuai Song、Hai-Chao Xu

  DOI：10.3762/bjoc.15.76

  日期：——

  A diastereoselective approach to axially chiral imidazopyridine-containing biaryls has been developed. The reactions proceed through a radical cyclization cascade to construct the biaryls with good to excellent central-to-axial chirality transfer.

  已经开发了一种非对映选择性的方法，用于轴向手性含咪唑并吡啶的联芳基。反应通过自由基环化级联进行，以构建具有良好至优异的中心-轴向手性转移的联芳基。
• 1H and 13C NMR spectra of some unsymmetric N,N′-dipyridyl ureas: spectral assignments and molecular conformation
  作者：Netai C. Singha、Dixit N. Sathyanarayana

  DOI：10.1039/a606800f

  日期：——

  The 1H NMR spectra of N-(2-pyridyl), N′-(3-pyridyl)ureas and N-(2-pyridyl), N′-(4-pyridyl)ureas in CDCl3 and (CD3)2CO have been assigned with the aid of COSY and NOE experiments and chemical shift and coupling constant correlations. The 13C NMR spectra in CDCl3 were analysed utilizing the HETCOR and proton coupled spectra. The 1H NMR spectra, NOE effects and MINDO/3 calculations have been utilized to show that the molecular conformation of these compounds has the 2-pyridyl ring coplanar with the urea plane with the N–H group hydrogen bonded to the nitrogen of the 2-pyridyl group on the other urea nitrogen while the 3/4-pyridyl group rotates rapidly about the N–C3/N–C4 bond.

  借助 COSY 和 NOE 实验以及化学位移和耦合常数相关性，分配了 N-(2-吡啶基)、Nâ²-(3-吡啶基)脲和 N-(2-吡啶基)、Nâ²-(4-吡啶基)脲在 CDCl3 和 (CD3)2CO 中的 1H NMR 光谱。利用 HETCOR 和质子耦合光谱分析了 CDCl3 中的 13C NMR 光谱。利用 1H NMR 光谱、NOE 效应和 MINDO/3 计算表明，这些化合物的分子构象是 2-吡啶基环与脲平面共面，NâH 基氢键与另一个脲氮上的 2-吡啶基氮相连，而 3/4 吡啶基围绕 NâC3/NâC4 键快速旋转。
• C-3 novel triterpenone with C-17 reverse amide derivatives as HIV inhibitors
  申请人：HETERO LABS LIMITED

  公开号：US11034718B2

  公开（公告）日：2021-06-15

  The invention relates to C-3 novel triterpenone with C-17 reverse amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.

  本发明涉及 C-3 新型三萜酮与 C-17 反向酰胺衍生物、相关化合物和药物组合物，可用于治疗病毒性疾病，特别是艾滋病病毒介导的疾病。
• WO2016/178092
  申请人：——

  公开号：——

  公开（公告）日：——