N-tert-butyldimethylsilylisopropyl formimidate | 172095-72-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: N-tert-butyldimethylsilylisopropyl formimidate
• 英文别名: propan-2-yl N-[tert-butyl(dimethyl)silyl]methanimidate
• CAS: 172095-72-6
• 化学式: C₁₀H₂₃NOSi
• 分子量: 201.384
• InChiKey: BLPWUXLKELOWSO-UHFFFAOYSA-N

物化性质

• 沸点：
  210.5±23.0 °C(Predicted)
• 密度：
  0.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氟代乙酰氯 、 N-tert-butyldimethylsilylisopropyl formimidate 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 isopropyl N-((Z)-1-((tert-butyldimethylsilyl)oxy)-2-fluorovinyl)formimidate
  参考文献：
  名称：

  A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy

  摘要：

  :The reaction of N-silylated iminoethers with 2-substituted acetyl chlorides yields activated 2-azadienes. These were shown to react with electron-deficient acetylenic dienophiles to yield pyridones. They also react with quinones to give the corresponding aromatized cycloadducts in good yields. The reaction of a-azadienes with activated nitriles provided a very practical route towards polysubstituted pyrimidones. A multicomponent protocol is reported which combines a N-t-butyldimethylsilyl iminoether, an acetyl chloride derivative and a dienophile in the presence of triethylamine without isolation of any intermediate. This provides an extremely practical and versatile route to various mono- and polycyclic azaaromatics with a predictable substitution pattern. Yields ranged from 43 % to 94 % for the complete sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01149-1
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 甲亚胺异丙酯 盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以73.5%的产率得到N-tert-butyldimethylsilylisopropyl formimidate
  参考文献：
  名称：

  WO2007/71358

  摘要：

  公开号：

文献信息

• Diastereoselective β-Hydroxyalkylation and β-Hydroxycarboxylation of Amides­ by a Diels-Alder Strategy
  作者：Léon Ghosez、Deogratias Ntirampebura

  DOI：10.1055/s-2002-34367

  日期：——

  Acid chlorides readily condensed with N-silylated imines in the presence of a base to generate 2-azadienes. These underwent Diels-Alder cycloadditions with a wide variety of aldehydes.. In most cases the cycloadditions were diastereoselective in favor of the 3,4-cis-oxazinone adducts. Ethanolysis stereoselectively yielded products of hydroxyalkylation or hydroxycarboxylation of the primary amides derived

  在碱的存在下，酰氯很容易与 N-甲硅烷基化亚胺缩合生成 2-氮杂二烯。这些经历了与多种醛的 Diels-Alder 环加成反应。在大多数情况下，环加成反应是非对映选择性的，有利于 3,4-顺式-恶嗪酮加合物。乙醇解立体选择性地产生衍生自初始酰氯的伯酰胺的羟烷基化或羟羧化产物。
• WO2008/9487
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2007/71358
  申请人：——

  公开号：——

  公开（公告）日：——
• A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy
  作者：Lon Ghosez、Eric Jnoff、Philippe Bayard、Francy Sainte、Renaud Beaudegnies

  DOI：10.1016/s0040-4020(98)01149-1

  日期：1999.3

  :The reaction of N-silylated iminoethers with 2-substituted acetyl chlorides yields activated 2-azadienes. These were shown to react with electron-deficient acetylenic dienophiles to yield pyridones. They also react with quinones to give the corresponding aromatized cycloadducts in good yields. The reaction of a-azadienes with activated nitriles provided a very practical route towards polysubstituted pyrimidones. A multicomponent protocol is reported which combines a N-t-butyldimethylsilyl iminoether, an acetyl chloride derivative and a dienophile in the presence of triethylamine without isolation of any intermediate. This provides an extremely practical and versatile route to various mono- and polycyclic azaaromatics with a predictable substitution pattern. Yields ranged from 43 % to 94 % for the complete sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.