(1'S*,2'S*,7a'S*)-1'-nitro-2'-phenylspiro[indene-2,3'-pyrrolizidine]-1,3-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1'S*,2'S*,7a'S*)-1'-nitro-2'-phenylspiro[indene-2,3'-pyrrolizidine]-1,3-dione
• 英文别名: 4-nitro-3-phenyl-spiro[hexahydropyrrolizine-5,2'-indane]-1',3'-dione；(6R,7R,8R)-7-nitro-6-phenylspiro[1,2,3,6,7,8-hexahydropyrrolizine-5,2'-indene]-1',3'-dione
• 化学式: C₂₁H₁₈N₂O₄
• 分子量: 362.385
• InChiKey: HBKXLBBZTMWSOG-KURKYZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  反式硝基苯乙烯 、 水合茚三酮 、 DL-脯氨酸 以 异丙醇 为溶剂， 反应 24.0h， 以75%的产率得到(1'S*,2'S*,7a'S*)-1'-nitro-2'-phenylspiro[indene-2,3'-pyrrolizidine]-1,3-dione
  参考文献：
  名称：

  茚并喹喔啉酮偶氮甲亚胺基团向β-硝基苯乙烯的区域和立体选择性1,3-偶极环加成反应：螺[茚并[1,2-b]喹喔啉-11,3'-吡咯并核苷]和螺[茚并[1,2-b]的合成]喹喔啉-1,2'-吡咯烷]

  摘要：

  在脯氨酸或肌氨酸和茚并喹喔啉酮中原位 获得的甲亚胺基化物在异丙醇中加热4-5天后与硝基苯乙烯反应，从而形成螺[茚并[1,2 - b ]喹喔啉-11,3'-吡咯并核苷]和螺[茚并[1,2 - b ]-喹喔啉-1,2'-吡咯烷]具有多种区域化学作用。

  DOI：

  10.1007/s10593-017-2074-0

文献信息

• Spiro indane-1,3-dione pyrrolizidine compounds synthesized by 1,3-dipolar cyclo-addition reaction
  作者：Gang Chen、Ya Wu、Xuefan Gu

  DOI：10.1515/hc.2011.023

  日期：2011.1.1

  Spiro indane-1,3-dione pyrrolizidine compounds were synthesized by the 1,3-dipolar cyclo-addition reaction of ninhydrin, L-proline and two kinds of alkene (chalcone and (E)-beta-aryl-nitrostyrene). All these reactions proceeded with good yield and with high regio- and stereoselectivity. It was found that the use of two kinds of alkene lead to different regioselectivity. In the structure of D1 and D2, the electron-withdrawing group (EWG; benzoyl group) is attached to C-3 and the phenyl group is at C-4 of the newly constructed pyrrolidine. In the structure of D3-D7, the EWG (nitro group) is at C-4 and the phenyl group is at C-3 of the newly constructed pyrrolidine.
• Synthesis of Spirooxindolo/Spiroindano Nitro Pyrrolizidines through Regioselective Azomethine Ylide Cycloaddition Reaction
  作者：Mahalingam Poornachandran、Ragavachary Raghunathan

  DOI：10.1080/00397910701462575

  日期：2007.8
• Regio- and stereoselective 1,3-dipolar cycloaddition of indenoquinoxalinone azomethine ylides to β-nitrostyrenes: synthesis of spiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizidines] and spiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidines]
  作者：Aleksey Yi. Barkov、Nikolay S. Zimnitskiy、Vladislav Yu. Korotaev、Igor B. Kutyashev、Vladimir S. Moshkin、Vyacheslav Ya. Sosnovskikh

  DOI：10.1007/s10593-017-2074-0

  日期：2017.4

  from proline or sarcosine and indenoquinoxalinones reacted with nitrostyrenes upon heating in isopropanol for 4–5 days, resulting in the formation of spiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizidines] and spiro[indeno[1,2-b]-quinoxaline-11,2'-pyrrolidines] with various regiochemistry.

  在脯氨酸或肌氨酸和茚并喹喔啉酮中原位 获得的甲亚胺基化物在异丙醇中加热4-5天后与硝基苯乙烯反应，从而形成螺[茚并[1,2 - b ]喹喔啉-11,3'-吡咯并核苷]和螺[茚并[1,2 - b ]-喹喔啉-1,2'-吡咯烷]具有多种区域化学作用。