5-Acetyl-1,2,3,4-tetrahydro-4a,9b-epidioxycarbazole | 150370-70-0

• 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: 5-Acetyl-1,2,3,4-tetrahydro-4a,9b-epidioxycarbazole
• 英文别名: 1-(14,15-Dioxa-8-azatetracyclo[7.4.2.01,9.02,7]pentadeca-2,4,6-trien-8-yl)ethanone
• CAS: 150370-70-0
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: BJKXTDHLJPGWQN-UHFFFAOYSA-N

物化性质

• 沸点：
  451.7±45.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Acetyl-1,2,3,4-tetrahydro-4a,9b-epidioxycarbazole 以 氘代氯仿 为溶剂， 反应 6.0h， 生成 N-Acetyl-1-azabenzo<8,9>cyclononane-2,7-dione
  参考文献：
  名称：

  单线态氧和二甲基二环氧乙烷氧化吲哚：通过氮酰化作用稳定化，以分离吲哚二氧环乙烷和环氧化物

  摘要：

  通过N-酰化作用的稳定作用可以分离出不稳定的吲哚二氧杂环丁烷2，其通过二甲基硫醚的脱氧作用转化为相应的吲哚环氧化物5。后者也通过二甲基二环氧乙烷氧化独立制备。

  DOI：

  10.1016/s0040-4039(00)73964-5
• 作为产物：
  描述：

  9-乙酰基-2,3,4,9-四氢-1H-咔唑 在 氧气 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-Acetyl-1-azabenzo<8,9>cyclononane-2,7-dione 、 5-Acetyl-1,2,3,4-tetrahydro-4a,9b-epidioxycarbazole
  参考文献：
  名称：

  Oxidation of N-Acylindoles by Dimethyldioxirane and Singlet Oxygen: Substituent Effects on Thermally Persistent Indole Epoxides and Dioxetanes

  摘要：

  Photooxygenation of the N-acylindoles 1a-d afforded the labile indole dioxetanes 2 and the relatively stable allylic hydroperoxides 3. The dioxetanes 2a,c,d were sufficiently stable for isolation and spectral characterization. Additionally, they were characterized by chemical transformations, namely reduction to the indole epoxides 5 by dimethyl sulfide, acid-catalyzed rearrangement to allylic hydroperoxides 3c,d, and thermolysis to the cleavage products 4. Oxidation of the N-acylindoles I with dimethyldioxirane afforded the epoxides 5, which were characterized on the basis of their spectral data and chemical transformations to the 2-indolinones 6 and 2-methyleneindoline 7. These decomposition products (except 7e) were fully characterized. The stability of the epoxides 5 depended on the substitution type, i.e., the carbazole epoxide 5c decomposed already at temperatures above ca. -50 degrees C, whereas the cyclopentindole epoxide 5b was stable at 20 degrees C for days. The latter was unequivocally characterized by X-ray analysis.

  DOI：

  10.1021/jo00089a016

文献信息

• Oxidation of indoles by singlet oxygen and dimethyldioxirane: Isolation of indole dioxetanes and epoxides by stabilization through nitrogen acylation
  作者：Waldemar Adam、Michael Ahrweiler、Markus Sauter、Bernd Schmiedeskamp

  DOI：10.1016/s0040-4039(00)73964-5

  日期：1993.8

  through N-acylation allowed the isolation of the labile indole dioxetanes 2, which were transformed by dimethyl sulfide deoxygenation to the corresponding indole epoxides 5; the latter were also independently prepared by dimethyldioxirane oxidation.

  通过N-酰化作用的稳定作用可以分离出不稳定的吲哚二氧杂环丁烷2，其通过二甲基硫醚的脱氧作用转化为相应的吲哚环氧化物5。后者也通过二甲基二环氧乙烷氧化独立制备。
• Oxidation of N-Acylindoles by Dimethyldioxirane and Singlet Oxygen: Substituent Effects on Thermally Persistent Indole Epoxides and Dioxetanes
  作者：Waldemar Adam、Michael Ahrweiler、Karl Peters、Bernd Schmiedeskamp

  DOI：10.1021/jo00089a016

  日期：1994.5

  Photooxygenation of the N-acylindoles 1a-d afforded the labile indole dioxetanes 2 and the relatively stable allylic hydroperoxides 3. The dioxetanes 2a,c,d were sufficiently stable for isolation and spectral characterization. Additionally, they were characterized by chemical transformations, namely reduction to the indole epoxides 5 by dimethyl sulfide, acid-catalyzed rearrangement to allylic hydroperoxides 3c,d, and thermolysis to the cleavage products 4. Oxidation of the N-acylindoles I with dimethyldioxirane afforded the epoxides 5, which were characterized on the basis of their spectral data and chemical transformations to the 2-indolinones 6 and 2-methyleneindoline 7. These decomposition products (except 7e) were fully characterized. The stability of the epoxides 5 depended on the substitution type, i.e., the carbazole epoxide 5c decomposed already at temperatures above ca. -50 degrees C, whereas the cyclopentindole epoxide 5b was stable at 20 degrees C for days. The latter was unequivocally characterized by X-ray analysis.