(4-(trimethylstannyl)pyridin-3-yl)carbamic acid tert-butyl ester | 209681-13-0

• 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: (4-(trimethylstannyl)pyridin-3-yl)carbamic acid tert-butyl ester
• 英文别名: [3-(tert-butoxycarbonylamino)-4-pyridyl]trimethyltin(IV)；Carbamic acid, [4-(trimethylstannyl)-3-pyridinyl]-, 1,1-dimethylethyl ester；tert-butyl N-(4-trimethylstannylpyridin-3-yl)carbamate
• CAS: 209681-13-0
• 化学式: C₁₃H₂₂N₂O₂Sn
• 分子量: 357.04
• InChiKey: QPLJGPWZMHSVHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Iodo-3,4-dimethoxy-2-(methoxymethoxy)benzene 、 (4-(trimethylstannyl)pyridin-3-yl)carbamic acid tert-butyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯胂 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以20%的产率得到tert-butyl N-[4-[3,4-dimethoxy-2-(methoxymethoxy)phenyl]pyridin-3-yl]carbamate
  参考文献：
  名称：

  Cross Coupling Strategies towards the Synthesis of the Streptonigrin CD Moiety

  摘要：

  DOI：

  10.3987/com-98-8455
• 作为产物：
  描述：

  三甲基氯化锡 、 N-叔丁氧羰基-3-氨基吡啶 在 n-BuLi 、 TMEDA 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到(4-(trimethylstannyl)pyridin-3-yl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  [3-(tert-Butoxycarbonylamino)-4-pyridyl]trimethyltin(IV), a Tetraorganotin Compound Containing an Unexpected Intramolecular Sn...O Interaction

  摘要：

  The configuration about the Sn centre in the title compound, [Sn(CH3)(3)(C10H13N2O2)], is intermediate between tetrahedral and trigonal bipyramidal. A weak intramolecular Sn ... O(carbonyl) interaction of 3.070(3) Angstrom gives rise to an intramolecular six-membered chelate ring, formed through the carbonyl O atom; this is a unique feature of tetraorganotin compounds. The title compound was prepared by consecutive reaction of 3-(tert-butoxycarbonylamino)pyridine with n-butyllithium and trimethyltin chloride.

  DOI：

  10.1107/s0108270197017459

文献信息

• Synthesis and Discovery of Pyrazine−Pyridine Biheteroaryl as a Novel Series of Potent Vascular Endothelial Growth Factor Receptor-2 Inhibitors
  作者：Gee-Hong Kuo、Aihua Wang、Stuart Emanuel、Alan DeAngelis、Rui Zhang、Peter J. Connolly、William V. Murray、Robert H. Gruninger、Jan Sechler、Angel Fuentes-Pesquera、Dana Johnson、Steven A. Middleton、Linda Jolliffe、Xin Chen

  DOI：10.1021/jm040099a

  日期：2005.3.1

  series of potent VEGFR-2 inhibitors. Compound 15, which had IC(50) = 0.084 microM at VEGFR-2, showed very modest selectivity against fibroblast growth factor receptor-2 (IC(50) = 0.21 microM), platelet-derived growth factor receptor (IC(50) = 0.36 microM), and glycogen synthase kinase-3 (IC(50) = 0.478 microM), while it exhibited more than 10-fold selectivity against epidermal growth factor receptor

  病理性血管生成与疾病状态相关，例如癌症，糖尿病性视网膜病，类风湿性关节炎，子宫内膜异位和牛皮癣。有许多证据表明，直接抑制血管内皮生长因子受体2（VEGFR-2）的激酶活性将导致血管生成的减少和肿瘤生长的抑制。尝试通过使用钯催化的CC键来优化细胞周期蛋白依赖性激酶1（CDK1）抑制剂，CN键形成反应组装不同的双杂芳基分子，从而意外地发现了吡嗪-吡啶双杂芳基作为一种新型的有效VEGFR- 2种抑制剂。化合物15在VEGFR-2处的IC（50）= 0.084 microM，对成纤维细胞生长因子受体2的选择性非常适中（IC（50）= 0.21 microM），血小板衍生的生长因子受体（IC（50）= 0.36 microM）和糖原合酶激酶3（IC（50）= 0.478 microM），而对表皮生长因子受体（IC（50 ）= 1.36 microM）和胰岛素R激酶（IC（50）= 1.69 micr
• Cross Coupling Strategies towards the Synthesis of the Streptonigrin CD Moiety
  作者：Cedric W. Holzapfel、Renier Crous、Catherine Dwyer

  DOI：10.3987/com-98-8455

  日期：——
• [3-(<i>tert</i>-Butoxycarbonylamino)-4-pyridyl]trimethyltin(IV), a Tetraorganotin Compound Containing an Unexpected Intramolecular Sn...O Interaction
  作者：R. Crous、C. W. Holzapfel、G. J. Kruger

  DOI：10.1107/s0108270197017459

  日期：1998.6.15

  The configuration about the Sn centre in the title compound, [Sn(CH3)(3)(C10H13N2O2)], is intermediate between tetrahedral and trigonal bipyramidal. A weak intramolecular Sn ... O(carbonyl) interaction of 3.070(3) Angstrom gives rise to an intramolecular six-membered chelate ring, formed through the carbonyl O atom; this is a unique feature of tetraorganotin compounds. The title compound was prepared by consecutive reaction of 3-(tert-butoxycarbonylamino)pyridine with n-butyllithium and trimethyltin chloride.