1,1a,4,8b-Tetrahydro-1,1-dimethylcyclopropa<1>benzazepine-2,3-dione | 137793-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,1a,4,8b-Tetrahydro-1,1-dimethylcyclopropa<1>benzazepine-2,3-dione
• CAS: 137793-13-6
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: BFGXMIVWRPTQOM-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  cis-2,2a,4,8b-Tetrahydro-2a-hydroxy-1,1,4-trimethylcyclobutaquinolin-3(1H)-one 在 碘 、 mercury(II) oxide 作用下， 以 苯 为溶剂， 反应 4.0h， 以28%的产率得到1,2-Dihydro-1,1,5-trimethylfuro<2,3-c>quinolin-4(5H)-one
  参考文献：
  名称：

  Photoinduced molecular transformations. 128. Regioselective [2 + 2] photocycloaddition of 3-acetoxyquinolin-2(1H)-one with alkenes and formation of furo[2,3-c]quinolin-4(5H)-ones, 1-benzazocine-2,3-diones, and cyclopropa[d]benz[1]azepine-2,3-diones via a .beta.-scission of cyclobutanoxyl radicals generated from the resulting [2 + 2] photoadducts

  摘要：

  We have found that [2 + 2]pi photoadducts can be obtained by the photoaddition of 3-acetoxyquinolin-2(1H)-one with acyclic and cyclic alkenes. The photoaddition of 3-acetoxy-2-quinolin-2(1H)-one with 2-methylpropene, 2,3-dimethyl-2-butene, and 2-methoxypropene thus afforded regioselective head-to-tail adducts in 59-97% yields. The photoaddition of 3-acetoxy-2-quinolin-2(1H)-one with cyclopentene and cyclohexene resulted in the formation of sterically disfavored cis-cisoid-cis photoadducts as the major products, with the accompanying formation of cis-transoid-cis photoadducts as the minor products in combined yields of 87 and 66%, respectively. The photolysis of the hypoiodites generated in situ from cyclobutanols derived from all of the photoadducts induced beta-scissions at the outer bonds of the corresponding cyclobutanoxyl radicals to give furo[2,3-c]quinolin-4(5H)-ones in 15-50% yields with an accompanying formation of 7- and 8-membered lactams arising from beta-scissions at the catacondensed bonds of the cyclobutanoxyl radicals in 2-62% yields. The molecular structure of one of the novel 7-membered lactams that successively fused with cyclopropane and cyclopentane rings was established to be trans-5,8,9,10,10a,10b-hexahydro-5-methylcyclopenta[3,4]cyclopropa[1,2-d]benzazepine-6,7-dione by X-ray crystallographic analysis. The pathways leading to the formation of all of these products arising from beta-scissions are discussed.

  DOI：

  10.1021/jo00028a037