4,5-dihydro-7H-[1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-7-one | 128581-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4,5-dihydro-7H-[1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-7-one
• 英文别名: 8,9-Dihydro-6H-1,3-dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-6-one；4,6-dioxa-12-azapentacyclo[10.6.1.02,10.03,7.015,19]nonadeca-1(18),2(10),3(7),8,15(19),16-hexaen-11-one
• CAS: 128581-38-4
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: RZXGIUMMRFBJQK-UHFFFAOYSA-N

物化性质

• 熔点：
  243.6-246 °C(Solvent: Chloroform ; Methanol)
• 沸点：
  524.8±50.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  40.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-7H-[1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-7-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 生成 hippadine
  参考文献：
  名称：

  A direct synthesis of pyrrolophenanthridone alkaloids

  摘要：

  DOI：

  10.1016/s0040-4039(00)76203-4
• 作为产物：
  描述：

  胡椒酸酰氯 在 palladium diacetate 吡啶 、 四丁基氯化铵 、 potassium acetate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4,5-dihydro-7H-[1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-7-one
  参考文献：
  名称：

  Synthetic Studies on Pyrrolophenanthridone Skeleton from 1-Benzoyl-7-iododihydroindole Derivatives Using Palladium-assisted Biaryl Coupling Reactions

  摘要：

  The biaryl coupling reaction of 1-benzoyl-7-iododihydroindole derivatives using Pd reagent was examined. 1-[(1,3-Benzodioxol-5-yl)carbonyl]-7-iodo-2,3-dihydroindole gave 4,5-dihydro-7H-[1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-7-one, which was formed by connection to a more hindered carbon, as a major product. 1-(3,4-Dimethoxybenzoyl)-7-iodo-2,3-dihydroindole gave oxoassoanine and 10,11-dimethoxy-4,5-dihydropyrrolo[3,2,1-de]phenanthridin-7-one in an almost equal ratio.

  DOI：

  10.3987/com-03-s10

文献信息

• Construction of pyrrolophenanthridinone scaffolds mediated by samarium(II) diiodide and access to natural product synthesis
  作者：Kenji Suzuki、Hiroki Iwasaki、Reika Domasu、Naho Hitotsuyanagi、Yuka Wakizaka、Mao Tominaga、Naoto Kojima、Minoru Ozeki、Masayuki Yamashita

  DOI：10.1016/j.tet.2015.06.067

  日期：2015.8

  Pyrrolophenanthridinone derivatives including the natural products were readily synthesized by samarium(II)-mediated reductive cyclization of aryl radical onto a benzene ring under mild reaction conditions. This methodology was applied to the concise synthesis of anhydrolycorinone, a natural pyrrolophenanthridinone and a precursor of hippadine and anhydrolycorine.

  通过sa（II）介导的芳基自由基在温和的反应条件下的还原环化反应，可以轻松合成包括天然产物在内的吡咯并菲蒽酮衍生物。该方法学被用于简并合成脱水氢化可的松，天然的吡咯并菲咯烷酮和河马碱和脱水氢化可的碱的前体。
• Regioselectivity in the Biaryl Coupling Reactions of 1-[(1,3-Benzodioxol-5-yl)methyl]-7-iodo-2,3-dihydroindole Using Palladium Reagent
  作者：Takashi Harayama、Akihiro Hori、Hitoshi Abe、Yasuo Takeuchi

  DOI：10.3987/com-05-s(t)5

  日期：——

  The biaryl coupling reaction of 1-[(1,3-benzodioxol-5-yl)methyl]-7-iodo-2,3-dihydroindole (1) using Pd(OAc)(2) gave selectively 4,5-dihydro-7H- [1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridine (4), which was formed by connection to a more hindered carbon, in 3.4 similar to 4.2:1 ratios.
• BLACK, DAVID ST. C.;KELLER, PAUL A.;KUMAR, NARESH, TETRAHEDRON LETT., 30,(1989) N2, C. 5807-5808
  作者：BLACK, DAVID ST. C.、KELLER, PAUL A.、KUMAR, NARESH

  DOI：——

  日期：——