2-(1-Diazoethyl)-1,3,3-trimethylcyclopentene | 153884-21-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 炔丙基型1，3-偶极有机化合物
• 英文名称: 2-(1-Diazoethyl)-1,3,3-trimethylcyclopentene
• CAS: 153884-21-0
• 化学式: C₁₀H₁₆N₂
• 分子量: 164.25
• InChiKey: DUYVAELALZYBSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1-Diazoethyl)-1,3,3-trimethylcyclopentene 以 丙酮 为溶剂， 反应 3.0h， 以6%的产率得到(Z)-1-Ethylidene-2-methylene-5,5-dimethylcyclopentane
  参考文献：
  名称：

  Reactions of methyl(2,5,5-trimethyl-l-cyclopenten-l-yl)carbene and the photochemistry of 2-(1-propynyl)-2,5,5-trimethylcyclopentanone

  摘要：

  Dienes 7 and 8 are formed both on photolysis of 1 and on triplet decomposition of diazo compound 14. These observations appear to imply that biradical 3, a photochemical intermediate formed from 1, closes to carbene 9, from which 7 and 8 result on migration of hydrogen. It is shown, however, that dienes 7 and 8 are secondary products formed both on photolysis of 1 and on decomposition of 14. Photodimer 28 is also formed on irradiation of 1, and it is suggested that 28 arises by 1,3 acyl shift of 1 to allenic ketone 29 followed by head-to-head dimerization of 29 at the beta,gamma double bond.

  DOI：

  10.1021/jo00076a022
• 作为产物：
  描述：

  1-Acetyl-2,2,5-trimethylcyclopent-5-ene tosylhydrazone 在 sodium methylate 作用下， 以64%的产率得到2-(1-Diazoethyl)-1,3,3-trimethylcyclopentene
  参考文献：
  名称：

  Reactions of methyl(2,5,5-trimethyl-l-cyclopenten-l-yl)carbene and the photochemistry of 2-(1-propynyl)-2,5,5-trimethylcyclopentanone

  摘要：

  Dienes 7 and 8 are formed both on photolysis of 1 and on triplet decomposition of diazo compound 14. These observations appear to imply that biradical 3, a photochemical intermediate formed from 1, closes to carbene 9, from which 7 and 8 result on migration of hydrogen. It is shown, however, that dienes 7 and 8 are secondary products formed both on photolysis of 1 and on decomposition of 14. Photodimer 28 is also formed on irradiation of 1, and it is suggested that 28 arises by 1,3 acyl shift of 1 to allenic ketone 29 followed by head-to-head dimerization of 29 at the beta,gamma double bond.

  DOI：

  10.1021/jo00076a022

文献信息

• Reactions of methyl(2,5,5-trimethyl-l-cyclopenten-l-yl)carbene and the photochemistry of 2-(1-propynyl)-2,5,5-trimethylcyclopentanone
  作者：D. Venugopal、Paul Margaretha、William C. Agosta

  DOI：10.1021/jo00076a022

  日期：1993.11

  Dienes 7 and 8 are formed both on photolysis of 1 and on triplet decomposition of diazo compound 14. These observations appear to imply that biradical 3, a photochemical intermediate formed from 1, closes to carbene 9, from which 7 and 8 result on migration of hydrogen. It is shown, however, that dienes 7 and 8 are secondary products formed both on photolysis of 1 and on decomposition of 14. Photodimer 28 is also formed on irradiation of 1, and it is suggested that 28 arises by 1,3 acyl shift of 1 to allenic ketone 29 followed by head-to-head dimerization of 29 at the beta,gamma double bond.