6,7-bis(3,4-dimethoxyphenyl)indolizine-5,8-dione | 156424-88-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 6,7-bis(3,4-dimethoxyphenyl)indolizine-5,8-dione
• CAS: 156424-88-3
• 化学式: C₂₄H₂₁NO₆
• 分子量: 419.434
• InChiKey: SIFJIUBZZKYSTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,7-bis(3,4-dimethoxyphenyl)indolizine-5,8-dione 在 10% palladium on active carbon 吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 甲酸 、 1,3-双(二苯基膦)丙烷 、 氢气 、 palladium diacetate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (+/-)-septicine
  参考文献：
  名称：

  Synthesis of (±)-septicine

  摘要：

  The total synthesis of the indolizidine alkaloid, (+/-)-septicine (5) (27% overall yield) in 8 steps from dimethyl squarate is presented. The key step of the synthesis involves the ring expansion of 2,3-bis-(3,4-dimethoxyphenyl)-4-(1-pyrrolo)cyclobutenone 12 to the corresponding indolizine-5,8-dione 6. The synthesis is highly convergent and thus could be used for the synthesis of a variety of analogs.

  DOI：

  10.1016/s0040-4020(01)80639-6
• 作为产物：
  描述：

  2,3-bis-(3,4-dimethoxyphenyl)-4-(1-pyrrolo)-4-trimethylsiloxycyclobutenone 在 iron(II) chloride 作用下， 生成 6,7-bis(3,4-dimethoxyphenyl)indolizine-5,8-dione
  参考文献：
  名称：

  Synthesis of (±)-septicine

  摘要：

  The total synthesis of the indolizidine alkaloid, (+/-)-septicine (5) (27% overall yield) in 8 steps from dimethyl squarate is presented. The key step of the synthesis involves the ring expansion of 2,3-bis-(3,4-dimethoxyphenyl)-4-(1-pyrrolo)cyclobutenone 12 to the corresponding indolizine-5,8-dione 6. The synthesis is highly convergent and thus could be used for the synthesis of a variety of analogs.

  DOI：

  10.1016/s0040-4020(01)80639-6

文献信息

• Efficient Synthesis of a New Structural Phenanthro[9,10,3‘,4‘]indolizidine Starting from Pyrrole
  作者：Kailiang Wang、Qingmin Wang、Runqiu Huang

  DOI：10.1021/jo701590p

  日期：2007.10.1

  A new structural phenanthroindolizidine, 2,3,6,7-tetramethoxyphenanthro[9,10,3('),4(')]indolizidine, has been synthesized efficiently from pyrrole. An important feature of this synthesis is that intramolecular oxidative coupling and rearrangement of 6,7-bis(3,4-dimethoxyphenyl)-8-methoxy-1,2,3-trihydroindolizin-5-one by using VOF3 and TFA have been achieved in one pot.
• Synthesis of (±)-septicine
  作者：Benjamin R. Yerxa、Kevin Yang、Harold W. Moore

  DOI：10.1016/s0040-4020(01)80639-6

  日期：1994.1

  The total synthesis of the indolizidine alkaloid, (+/-)-septicine (5) (27% overall yield) in 8 steps from dimethyl squarate is presented. The key step of the synthesis involves the ring expansion of 2,3-bis-(3,4-dimethoxyphenyl)-4-(1-pyrrolo)cyclobutenone 12 to the corresponding indolizine-5,8-dione 6. The synthesis is highly convergent and thus could be used for the synthesis of a variety of analogs.