2-[diazo(phenyl)methyl]phenyl crotonate | 1449004-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[diazo(phenyl)methyl]phenyl crotonate
• 英文别名: [2-[diazo(phenyl)methyl]phenyl] (E)-but-2-enoate
• CAS: 1449004-10-7
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: ZXGAULNSKWUJOJ-KRXBUXKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  28.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[diazo(phenyl)methyl]phenyl crotonate 以 甲苯 为溶剂， 反应 2.0h， 生成 (6Z)-6-[(3E)-2-oxo-1-phenylpent-3-enylidene]cyclohexa-2,4-dienone
  参考文献：
  名称：

  Intramolecular photo-cyclization and consecutive rearrangement reactions of diazo-functionalized olefin-esters

  摘要：

  A study on intramolecular photo-cyclization reactions with diazo-functionalized olefin-esters is presented. On irradiation of diphenyl diazo methane esters of cinnamic acids, not only the expected addition to the C=C double bond is observed, yielding cyclopropanes, but also the addition to the carboxylic C=O double bond is postulated as an intermediate. These formed intermediates undergo a rearrangement to cyclobutanones which further rearrange photo-assisted to oxetanes.Both were isolated and characterized. The reaction progress, the impact of the irradiation wavelength and solvent as well as the influence of the electron density of the olefin on the product distribution is described. Also, the detailed reaction mechanism for the photo-reaction cascade is discussed. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.12.005
• 作为产物：
  描述：

  2-{phenyl[2-(p-tosyl)hydrazono]methyl}phenyl crotonate 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.75h， 生成 2-[diazo(phenyl)methyl]phenyl crotonate
  参考文献：
  名称：

  Intramolecular photo-cyclization and consecutive rearrangement reactions of diazo-functionalized olefin-esters

  摘要：

  A study on intramolecular photo-cyclization reactions with diazo-functionalized olefin-esters is presented. On irradiation of diphenyl diazo methane esters of cinnamic acids, not only the expected addition to the C=C double bond is observed, yielding cyclopropanes, but also the addition to the carboxylic C=O double bond is postulated as an intermediate. These formed intermediates undergo a rearrangement to cyclobutanones which further rearrange photo-assisted to oxetanes.Both were isolated and characterized. The reaction progress, the impact of the irradiation wavelength and solvent as well as the influence of the electron density of the olefin on the product distribution is described. Also, the detailed reaction mechanism for the photo-reaction cascade is discussed. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.12.005