allyl N-isopropyl-4-methoxybenzimidate | 1252580-91-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: allyl N-isopropyl-4-methoxybenzimidate
• CAS: 1252580-91-8
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: XEASDURGWKAAKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  二氯乙酰氯 、 allyl N-isopropyl-4-methoxybenzimidate 在 三乙胺 作用下， 以 苯 为溶剂， 反应 2.25h， 以76%的产率得到4-(allyloxy)-3,3-dichloro-1-isopropyl-4-(4-methoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  Synthesis of Chlorinated Bicyclic C-Fused Tetrahydrofuro[3,2-c]azetidin-2-ones

  摘要：

  Some bicyclic C-fused chlorinated tetrahydrofuro[3,2-c]azetidin-2-ones were prepared by a fairly general route involving Staudinger reaction of allylic/propargylic imidates with dichloroketene followed by highly diastereoselective CuCl/PMDETA-catalyzed 5-exo-trig/dig chlorine atom transfer radical cyclization. An oxepan-fused beta-lactam was also prepared similarly by 7-endo-trig cyclization. Synthetic application of the side chain chlorine atom of the products was demonstrated by its substitution in one of the products with azide followed by azide-alkyne click reaction with phenylacetylene to obtain a 1,2,3-triazolyltetrahydrofuro[3,2-c]azetidin-2-one.

  DOI：

  10.1021/jo101045z
• 作为产物：
  描述：

  N-isopropyl-4-methoxybenzimidoyl chloride 、 烯丙醇 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 21.25h， 以100%的产率得到allyl N-isopropyl-4-methoxybenzimidate
  参考文献：
  名称：

  Synthesis of Chlorinated Bicyclic C-Fused Tetrahydrofuro[3,2-c]azetidin-2-ones

  摘要：

  Some bicyclic C-fused chlorinated tetrahydrofuro[3,2-c]azetidin-2-ones were prepared by a fairly general route involving Staudinger reaction of allylic/propargylic imidates with dichloroketene followed by highly diastereoselective CuCl/PMDETA-catalyzed 5-exo-trig/dig chlorine atom transfer radical cyclization. An oxepan-fused beta-lactam was also prepared similarly by 7-endo-trig cyclization. Synthetic application of the side chain chlorine atom of the products was demonstrated by its substitution in one of the products with azide followed by azide-alkyne click reaction with phenylacetylene to obtain a 1,2,3-triazolyltetrahydrofuro[3,2-c]azetidin-2-one.

  DOI：

  10.1021/jo101045z

文献信息

• Palladium-Catalyzed Tunable Functionalization of Allylic Imidates: Regioselective Aminodiacetoxylation and Aziridination
  作者：Sunliang Cui、Lukasz Wojtas、Jon C. Antilla

  DOI：10.1002/anie.201103500

  日期：2011.9.12

  In control: The title reaction has been shown to be highly general and efficient, thus exhibiting valuable potential synthetic utility (see scheme; DMF=N,N‐dimethylformamide). Isotope labeling and two proposed mechanistic pathways, which invoke a PdII/PdIV catalytic cycle, show divergent CN and CO bond formation.

  在对照中：标题反应已被证明是高度通用和有效的，因此具有潜在的合成实用价值（参见方案； DMF = N，N-二甲基甲酰胺）。同位素标记和提出的两种机制途径（称为Pd II / Pd IV催化循环）显示出不同的CN和CO键形成。