o-allyloxyphenoxyacetyl chloride | 1181407-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: o-allyloxyphenoxyacetyl chloride
• 英文别名: 2-(2-Prop-2-enoxyphenoxy)acetyl chloride；2-(2-prop-2-enoxyphenoxy)acetyl chloride
• CAS: 1181407-30-6
• 化学式: C₁₁H₁₁ClO₃
• 分子量: 226.66
• InChiKey: YLVKHYXOAZPIRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  o-allyloxyphenoxyacetyl chloride 、 N1,N2双[(4-甲氧基苯基)亚甲基]-1,2-乙二胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以35%的产率得到
  参考文献：
  名称：

  Sequential Staudinger Ketene−Imine Cycloaddition, RCM Approach to Highly Rigid Macrocrocyclic Bisazetidinones

  摘要：

  An efficient approach to highly rigid macrocyclic bisazetidinones with interesting structural feature was achieved via sequential Staudinger ketene-imine cycloaddition of o-allyloxyphenoxyketene and bis-arylidenediamines followed by RCM. The ketene-imine cycloaddition afforded the corresponding bis-o-allyloxyphenoxyazetidinones as the cis-cis diastereomers, exclusively obtained as a mixture of cis-syn-cis and cis-anti-cis. RCM of the latter using Grubbs' catalysts afforded good yields of the corresponding novel macrocyclic bisazetidinones. The cis-anti-cis bisazetidinones are readily identified by (1)H NMR using Eu(hfc)(3) chiral shift reagent. (1)H NMR indicated the high shielding effect of the aryl substituents on one of the ortho-H's of the condensed phenylene ring, and VT (1)H NMR indicates the highly restricted rotation of the aryl groups, thus offering a highly rigid system.

  DOI：

  10.1021/jo100679d
• 作为产物：
  描述：

  2-(2-allyloxyphenoxy)acetic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 o-allyloxyphenoxyacetyl chloride
  参考文献：
  名称：

  Sequential Staudinger Ketene−Imine Cycloaddition, RCM Approach to Highly Rigid Macrocrocyclic Bisazetidinones

  摘要：

  An efficient approach to highly rigid macrocyclic bisazetidinones with interesting structural feature was achieved via sequential Staudinger ketene-imine cycloaddition of o-allyloxyphenoxyketene and bis-arylidenediamines followed by RCM. The ketene-imine cycloaddition afforded the corresponding bis-o-allyloxyphenoxyazetidinones as the cis-cis diastereomers, exclusively obtained as a mixture of cis-syn-cis and cis-anti-cis. RCM of the latter using Grubbs' catalysts afforded good yields of the corresponding novel macrocyclic bisazetidinones. The cis-anti-cis bisazetidinones are readily identified by (1)H NMR using Eu(hfc)(3) chiral shift reagent. (1)H NMR indicated the high shielding effect of the aryl substituents on one of the ortho-H's of the condensed phenylene ring, and VT (1)H NMR indicates the highly restricted rotation of the aryl groups, thus offering a highly rigid system.

  DOI：

  10.1021/jo100679d

文献信息

• Sequential Diimination, Staudinger [2 + 2] Ketene–Imine Cycloaddition, and Ring-Closing Metathesis (RCM) Reactions: In Route to Bis(4-spiro-fused-β-lactams)-Based Macrocycles
  作者：Osama M. Habib、Asaad S. Mohamed、Yehia A. Ibrahim、Nouria A. Al-Awadi

  DOI：10.1021/acs.joc.1c01576

  日期：2021.11.5

  Based on sequential organic transformations, that is, diimine formation, Staudinger [2 + 2] ketene–imine cycloaddition, and ring-closing metathesis (RCM) reactions, the synthesis with full structural identification including NMR and HRMS spectral data along with single X-ray diffraction analysis (for anti7b, anti8b, syn9a, and anti9b) of the first syn/anti bis-4-spiro-β-lactams-based azacrown ethers

  基于顺序有机转化，即二亚胺形成、施陶丁格 [2 + 2] 烯酮-亚胺环加成和闭环复分解 (RCM) 反应，合成具有完整的结构鉴定，包括 NMR 和 HRMS 光谱数据以及单个 X-报道了第一种基于顺/反双-4-螺-β-内酰胺的氮杂冠醚（7a、b-9a、b ）的射线衍射分析（针对抗7b、抗8b、顺9a和抗9b ）。