8,8-dibromo-1-tert-butylbicyclo<5.1.0>octane | 108857-02-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 8,8-dibromo-1-tert-butylbicyclo<5.1.0>octane
• 英文别名: 8,8-Dibromo-1-tert-butylbicyclo[5.1.0]octane
• CAS: 108857-02-9
• 化学式: C₁₂H₂₀Br₂
• 分子量: 324.099
• InChiKey: GKZCITCIJXVAEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  8,8-dibromo-1-tert-butylbicyclo<5.1.0>octane 在 甲基锂 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 氘代氯仿 、 正戊烷 为溶剂， 反应 0.75h， 生成 1-tert-butylcycloheptene
  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：

  三溴甲烷 、 1-tert-butylcycloheptene 在 potassium tert-butylate 作用下， 以 正戊烷 为溶剂， 反应 8.0h， 以37%的产率得到8,8-dibromo-1-tert-butylbicyclo<5.1.0>octane
  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

• 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：——