Methyl 5-[(2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oxy]pent-2-ynoate | 189142-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 5-[(2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oxy]pent-2-ynoate
• CAS: 189142-23-2
• 化学式: C₁₁H₁₆N₂O₅
• 分子量: 256.258
• InChiKey: IYYDQZRTYLBSGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  78.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 5-[(2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oxy]pent-2-ynoate 在 吡啶 、 四(三苯基膦)钯 、 三正丁基氢锡 作用下， 以 甲苯 、 苯 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Formal Intramolecular (4 + 1)-Cycloaddition of Dialkoxycarbenes: Control of the Stereoselectivity and a Mechanistic Portrait

  摘要：

  The stereoselective synthesis of 5-5, 6-5, and 7-5 fused O-heterocyclic compounds is reported. The key reaction is a formal intramolecular (4 + 1)-cycloaddition involving a dialkox-ycarbene and an electron-deficient diene where the stereo-selectivity is dependent on the length of the tether. An analysis of the stereochemical outcome of this reaction sheds light on its complex mechanistic picture. High-level calculations were used to support the proposed mechanistic portrait.

  DOI：

  10.1021/ja211927b
• 作为产物：
  描述：

  2-acetoxy-2-methoxy-5,5-dimethyl-Δ³-1,3,4-oxadiazoline 在 正丁基锂 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 49.0h， 生成 Methyl 5-[(2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oxy]pent-2-ynoate
  参考文献：
  名称：

  Reactions of dialkoxycarbenes with tethered triple bonds to form heterocyclic compounds

  摘要：

  从相应的氧代二氮杂环产生的带有三重键的二烷氧基卡宾与带有锁链炔基团的分子内环化，形成3,3-二烷氧基乙烯基卡宾/1,3-二极体中间体。卡宾环化的区域选择性高度取决于炔基取代基的性质。在生成外环乙烯基卡宾的情况下，乙烯基卡宾中间体可以与适当的烯烃或炔基进行有用的[3+2]环加成。这种方法可以快速构建一些有趣的杂环环系统。关键词：卡宾，二烷氧基卡宾，乙烯基二烷氧基卡宾，杂环。

  DOI：

  10.1139/v97-016

文献信息

• Formal Intramolecular (4 + 1)-Cycloaddition of Dialkoxycarbenes: Control of the Stereoselectivity and a Mechanistic Portrait
  作者：Francis Beaumier、Marianne Dupuis、Claude Spino、Claude Y. Legault

  DOI：10.1021/ja211927b

  日期：2012.4.4

  The stereoselective synthesis of 5-5, 6-5, and 7-5 fused O-heterocyclic compounds is reported. The key reaction is a formal intramolecular (4 + 1)-cycloaddition involving a dialkox-ycarbene and an electron-deficient diene where the stereo-selectivity is dependent on the length of the tether. An analysis of the stereochemical outcome of this reaction sheds light on its complex mechanistic picture. High-level calculations were used to support the proposed mechanistic portrait.
• Reactions of dialkoxycarbenes with tethered triple bonds to form heterocyclic compounds
  作者：Karim Kassam、John Warkentin

  DOI：10.1139/v97-016

  日期：1997.2.1

  Dialkoxycarbenes with a tethered triple bond, generated from the corresponding oxadiazolines, undergo an intramolecular cyclization with the tethered alkyne moiety to give 3,3-dialkoxyvinylcarbene/1,3-dipole intermediates. The regioselectivity of the carbene cyclization is highly dependent upon the nature of the alkyne substituent. In the cases where an exocyclic vinylcarbene is generated, the vinylcarbene intermediate can undergo a synthetically useful [3 + 2] cycloaddition with either an appropriate olefin or an alkyne. This approach allows the rapid construction of some interesting heterocyclic ring systems. Keywords: carbene, dialkoxycarbene, vinylogous dialkoxycarbene, heterocycle.

  从相应的氧代二氮杂环产生的带有三重键的二烷氧基卡宾与带有锁链炔基团的分子内环化，形成3,3-二烷氧基乙烯基卡宾/1,3-二极体中间体。卡宾环化的区域选择性高度取决于炔基取代基的性质。在生成外环乙烯基卡宾的情况下，乙烯基卡宾中间体可以与适当的烯烃或炔基进行有用的[3+2]环加成。这种方法可以快速构建一些有趣的杂环环系统。关键词：卡宾，二烷氧基卡宾，乙烯基二烷氧基卡宾，杂环。