2',3',5',6',8',8a'-hexahydrodispiro[indole-3,1'-indolizine-7',2''-[1,3]dioxolane] | 136061-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: 2',3',5',6',8',8a'-hexahydrodispiro[indole-3,1'-indolizine-7',2''-[1,3]dioxolane]
• CAS: 136061-54-6；130627-36-0；130627-32-6
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: FSDJDOHFCPBXDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  461.7±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  34.06
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2',3',5',6',8',8a'-hexahydrodispiro[indole-3,1'-indolizine-7',2''-[1,3]dioxolane] 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 15.5h， 生成 3,4,6,7,12,12b-Hexahydro-1H-indolo[2,3-a]quinolizin-2-one
  参考文献：
  名称：

  Synthetic applications of protected 2-aryl-4-piperidones. 7. Synthesis of 1-ethylindolo[2,3-a]quinolizidin-2-one

  摘要：

  The synthesis of 1-ethylindolo[2,3-a]quinolizidin-2-one (1) by the intramolecular cyclization of protected N-(2-hydroxyethyl)-2-[1-(phenylsulfonyl)-3-indolyl]-4-piperidone 15 by the action of K(t)BuO and further acid treatment is reported. The methodology has been first carried out for its deethyl analogue 2 from (hydroxyethyl)piperidine 14 and has shown to be a good general method to reach indolo[2,3-a]quinolizidin-2-one systems. Compound 1 has also been obtained by an unusual rearrangement in acidic medium of 7-ethylhexahydropyrido[1',2':1,2]pyrazino[4,3-a]indole.

  DOI：

  10.1021/jo00022a015
• 作为产物：
  描述：

  N-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-1-(1-(phenylsulfonyl)-1H-indol-3-yl)methanimine 在 potassium tert-butylate 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 16.5h， 生成 2',3',5',6',8',8a'-hexahydrodispiro[indole-3,1'-indolizine-7',2''-[1,3]dioxolane]
  参考文献：
  名称：

  Synthetic applications of protected 2-aryl-4-piperidones. 7. Synthesis of 1-ethylindolo[2,3-a]quinolizidin-2-one

  摘要：

  The synthesis of 1-ethylindolo[2,3-a]quinolizidin-2-one (1) by the intramolecular cyclization of protected N-(2-hydroxyethyl)-2-[1-(phenylsulfonyl)-3-indolyl]-4-piperidone 15 by the action of K(t)BuO and further acid treatment is reported. The methodology has been first carried out for its deethyl analogue 2 from (hydroxyethyl)piperidine 14 and has shown to be a good general method to reach indolo[2,3-a]quinolizidin-2-one systems. Compound 1 has also been obtained by an unusual rearrangement in acidic medium of 7-ethylhexahydropyrido[1',2':1,2]pyrazino[4,3-a]indole.

  DOI：

  10.1021/jo00022a015

文献信息

• Synthetic studies on indole alkaloids. II. Applications of phenylsulfonylindoles on intramolecular cyclizations
  作者：Mario Rubiralta、Anna Diez、Cristina Vila

  DOI：10.1016/s0040-4039(00)89061-9

  日期：1990.1

  The synthesis of indolo[2,3-a]quinolizidin-2-one 15 is reported through the potassium tert-butoxide cyclization of N-hydroxyethyl-2-[1-(phenylsulfonyl)-3-indolyl]-4-piperidone ethylene acetal (5) into 3-spiroindolenine intermediate 6. Anhydrous acid treatment of 6 leads to the rearranged 2,3-indole substituted compound 14. The reactivity of intermediate 6 will be further applied to construct ring C

  通过N-羟乙基-2- [1-（苯基磺酰基）-3-吲哚基] -4-哌啶酮乙烯缩醛的叔丁醇钾环化反应，报道了吲哚[2,3 - a ]喹啉基-2-酮15的合成。（5）成3-螺吲哚中间体6。6的无水酸处理导致2,3-吲哚取代的化合物14重排。的中间反应6将进一步施加到构造的环C马钱子和白坚木属框架。