2-tert-butyl-1,3-cyclooctadiene | 16240-44-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2-tert-butyl-1,3-cyclooctadiene
• 英文别名: 2-tert.-Butyl-1,3-cyclooctadien；(1E,3Z)-2-tert-butylcycloocta-1,3-diene
• CAS: 16240-44-1
• 化学式: C₁₂H₂₀
• 分子量: 164.291
• InChiKey: ZKSBTYAZSBKZFV-NKTIYDDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-tert-butyl-1,3-cyclooctadiene 以 苯 为溶剂， 生成 7-tert-butylbicyclo<4.2.0>oct-7-ene
  参考文献：
  名称：

  Cumulene photochemistry: photoreactions of a strained 1,2-cyclooctadiene

  摘要：

  The singlet and triplet photoreactions of 1-tert-butyl-1,2-cyclooctadiene (1) are described. This is the first example of an isolable eight-membered ring allene and is predicted to have a bent allenic unit. Triplet reactions of 1 are phase dependent. Benzene-sensitized irradiation affords products of hydrogen abstraction at tert-butyl or ring carbons in vapor phase or solution phase, respectively. Direct irradiation of thoroughly degassed pentane solutions at 254 nm affords primarily 3-tert-butylbicyclo[3.3.0]oct-2-ene and other products that are attributed to initial excited-state 1,2-hydrogen migration to a vinylcarbene. Independent generation of this vinylcarbene gives a similar collection of products, which include an isolable bicyclo[5.1.0]oct-1(8)-ene. Irradiation of 1 in oxygenated solutions yields tert-butylcycloheptene (15), apparently through loss of carbon monoxide from an intermediate cyclopropanone. Oxidation of 1 with m-CPBA also leads efficiently to 15.

  DOI：

  10.1021/jo00022a029
• 作为产物：
  描述：

  3-tert-butyl-2-cycloocten-1-one 在 sodium methylate 作用下， 以 苯 为溶剂， 反应 14.0h， 生成 2-tert-butyl-1,3-cyclooctadiene
  参考文献：
  名称：

  Cumulene photochemistry: photoreactions of a strained 1,2-cyclooctadiene

  摘要：

  The singlet and triplet photoreactions of 1-tert-butyl-1,2-cyclooctadiene (1) are described. This is the first example of an isolable eight-membered ring allene and is predicted to have a bent allenic unit. Triplet reactions of 1 are phase dependent. Benzene-sensitized irradiation affords products of hydrogen abstraction at tert-butyl or ring carbons in vapor phase or solution phase, respectively. Direct irradiation of thoroughly degassed pentane solutions at 254 nm affords primarily 3-tert-butylbicyclo[3.3.0]oct-2-ene and other products that are attributed to initial excited-state 1,2-hydrogen migration to a vinylcarbene. Independent generation of this vinylcarbene gives a similar collection of products, which include an isolable bicyclo[5.1.0]oct-1(8)-ene. Irradiation of 1 in oxygenated solutions yields tert-butylcycloheptene (15), apparently through loss of carbon monoxide from an intermediate cyclopropanone. Oxidation of 1 with m-CPBA also leads efficiently to 15.

  DOI：

  10.1021/jo00022a029

文献信息

• Small-ring cyclic cumulenes: Synthesis of a kinetically stable eight membered ring allene
  作者：John D Price、Richard P Johnson

  DOI：10.1016/s0040-4039(00)85036-4

  日期：1986.1

  1-tert-Butyl-1,2-cycloctadiene is prepared in four steps from cycloheptanone, and is found to be stable to dimerization.

  从环庚酮分四步制备1-叔丁基-1，2-环戊二烯，发现对二聚反应稳定。
• Base-promoted reactions of epoxides. V. 1-Alkylcycloalkene oxides
  作者：J. K. Crandall、Luan-Ho Chang Lin

  DOI：10.1021/jo01270a043

  日期：1968.6
• Zountsas, Johannes; Kreuzer, Matthias; Meier, Herbert, Angewandte Chemie, 1983, vol. 95, # 8, p. 638 - 639
  作者：Zountsas, Johannes、Kreuzer, Matthias、Meier, Herbert

  DOI：——

  日期：——
• PRICE J. D.; JOHNSON R. P., TETRAHEDRON LETT., 27,(1986) N 39, 4679-4682
  作者：PRICE J. D.、 JOHNSON R. P.

  DOI：——

  日期：——