1'-benzyl-5'-methoxy-1',3'-dihydrospiro-[cyclopropane-1,3'-indol]-2'-one | 289906-68-9

• 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: 1'-benzyl-5'-methoxy-1',3'-dihydrospiro-[cyclopropane-1,3'-indol]-2'-one
• 英文别名: 1'-benzyl-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-one；1'-Benzyl-5'-methoxyspiro[cyclopropane-1,3'-indole]-2'-one
• CAS: 289906-68-9
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: ACUYDYOHBZZOID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1'-benzyl-5'-methoxy-1',3'-dihydrospiro-[cyclopropane-1,3'-indol]-2'-one 在 氨 、 sodium 、 magnesium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 60.22h， 生成 horsfiline
  参考文献：
  名称：

  摘要：

  We report a short synthetic route to (+/-)-horsfiline that provides the racemate in five steps from commercially available, substituted isatin in 41% overall yield. Efficient entry into the spiro[oxindole-pyrrolidine] ring system is possible through the application of the cyclopropane opening/ring expansion chemistry we have described with MgI2 as a bifunctional catalyst.

  DOI：

  10.1002/1522-2675(20000607)83:6<1175::aid-hlca1175>3.0.co;2-d
• 作为产物：
  描述：

  1H-吲哚-2,3-二酮,5-甲氧基-1-(苯基甲基)- 在 sodium hydride 、 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.75h， 生成 1'-benzyl-5'-methoxy-1',3'-dihydrospiro-[cyclopropane-1,3'-indol]-2'-one
  参考文献：
  名称：

  摘要：

  We report a short synthetic route to (+/-)-horsfiline that provides the racemate in five steps from commercially available, substituted isatin in 41% overall yield. Efficient entry into the spiro[oxindole-pyrrolidine] ring system is possible through the application of the cyclopropane opening/ring expansion chemistry we have described with MgI2 as a bifunctional catalyst.

  DOI：

  10.1002/1522-2675(20000607)83:6<1175::aid-hlca1175>3.0.co;2-d

文献信息

• Domino Corey–Chaykovsky Reaction for One-Pot Access to Spirocyclopropyl Oxindoles
  作者：Saumen Hajra、Sayan Roy、SK Abu Saleh

  DOI：10.1021/acs.orglett.8b01840

  日期：2018.8.3

  The development of the sequential Corey–Chaykovsky reactions of isatins, spiroepoxy-, or spiroaziridine oxindoles with sulfur ylide has led to the discovery of a unique reaction mode that allows easy and direct one-pot access to a range of spirocyclopropyl oxindoles.

  靛红，螺环氧基或螺氮丙啶与吲哚硫醇的连续Corey-Chaykovsky反应的发展导致发现了一种独特的反应模式，该模式可以轻松，直接地一锅接触一系列螺环丙基羟吲哚。
• A Rapid Three-Component MgI₂-Mediated Synthesis of 3,3-Pyrollidinyl Spirooxindoles
  作者：Victoria Helan、Allie Mills、David Drewry、Daniel Grant

  DOI：10.1021/jo101077g

  日期：2010.10.1

  The rapid synthesis of 3,3-pyrrolidinyl-spirooxindole cores from readily available cyclopropyl spirooxindoles and commercially available aldehydes, amines, and sulfonamides is reported. This general procedure utilizes microwave heating to access a biologically privileged scaffold in an efficient route amenable to library population.
• ——
  作者：Christian Fischer、Christiane Meyers、Erick M. Carreira

  DOI：10.1002/1522-2675(20000607)83:6<1175::aid-hlca1175>3.0.co;2-d

  日期：2000.6.7

  We report a short synthetic route to (+/-)-horsfiline that provides the racemate in five steps from commercially available, substituted isatin in 41% overall yield. Efficient entry into the spiro[oxindole-pyrrolidine] ring system is possible through the application of the cyclopropane opening/ring expansion chemistry we have described with MgI2 as a bifunctional catalyst.