2,4-dimethyl-5-nitro-2,3-dihydrobenzo<2,3>furan | 140427-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,4-dimethyl-5-nitro-2,3-dihydrobenzo<2,3>furan
• 英文别名: 2,3-dihydro-2,4-dimethyl-5-nitrobenzofuran；2,4-Dimethyl-5-nitro-2,3-dihydro-1-benzofuran；2,4-dimethyl-5-nitro-2,3-dihydro-1-benzofuran
• CAS: 140427-40-3
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: YVXBOPIYLINMLL-UHFFFAOYSA-N

物化性质

• 沸点：
  308.1±41.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-5-nitro-2,3-dihydrobenzo<2,3>furan 在 盐酸 、 sodium dithionate 、 titanium(III) chloride 、 sodium nitrite 作用下， 以 盐酸 、 溶剂黄146 为溶剂， 反应 3.17h， 生成 2,4-二甲基-2,3-二氢-1-苯并呋喃
  参考文献：
  名称：

  The fischer indolisation reaction and the synthesis of dihydroindenoindoles

  摘要：

  The Fischer reaction between indanones and certain alkoxyarylhydrazines fails; the indanones are returned unreacted and the arylhydrazines are converted into the corresponding alkoxy-2-chloroarylamines and other products. A new N-amination route to arylhydrazines from the arylamines has been developed and it has been demonstrated that problems with the indolisation of alkoxyarylhydrazones can be circumvented by ring closures of their O-tosylated analogues. Some results using the Lepke synthesis of indoles are recorded.

  DOI：

  10.1016/s0040-4020(01)81911-6
• 作为产物：
  描述：

  4-硝基间甲苯酚 在 caesium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 2,4-dimethyl-5-nitro-2,3-dihydrobenzo<2,3>furan
  参考文献：
  名称：

  作为神经递质5-羟色胺的旋转受限酚类似物的吡喃并[3,2-e]吲哚和吡喃并[2,3-f]吲哚的合成

  摘要：

  已经完成了神经递质5-羟色胺的两个受旋转限制的酚类类似物（1a和1b）的合成。概述了形成这些靶标模板的8.9-二氢吡喃并[3,2-e]吲哚（13a）和7,8-二氢吡喃并[2,3-f]吲哚（13b）的合成。这些新颖的熔融吲哚代表5-羟基吲哚的旋转受限的酚类似物。使用克莱森重排，烯烃羟基化和分子内Mitsunobu反应的反应序列形成稠合的二氢吡喃环。

  DOI：

  10.1016/s0040-4020(01)88200-4

文献信息

• The synthesis of pyrano[3,2-e]indoles and pryano[2,3-f]indoles as rotationally restricted phenolic analogs of the neurotransmitter serotonin
  作者：John E. Macor、Kevin Ryan、Michael E. Newman

  DOI：10.1016/s0040-4020(01)88200-4

  日期：1992.1

  The synthesis of two rotationally restricted phenolic analogs (1a and 1b) of the neurotransmitter serotonin have been accomplished. The syntheses of 8.9-dihydropyrano[3,2-e]indole (13a) and 7,8-dihydropyrano[2,3-f]indole (13b), which formed the template for these targets, are outlined. These novel fused-indoles represent rotationally restricted phenolic analogs of 5-hydroxyindole. The reaction sequence

  已经完成了神经递质5-羟色胺的两个受旋转限制的酚类类似物（1a和1b）的合成。概述了形成这些靶标模板的8.9-二氢吡喃并[3,2-e]吲哚（13a）和7,8-二氢吡喃并[2,3-f]吲哚（13b）的合成。这些新颖的熔融吲哚代表5-羟基吲哚的旋转受限的酚类似物。使用克莱森重排，烯烃羟基化和分子内Mitsunobu反应的反应序列形成稠合的二氢吡喃环。
• The fischer indolisation reaction and the synthesis of dihydroindenoindoles
  作者：David W. Brown、Mary F. Mahon、Aleyamma Ninan、Malcolm Sainsbury、Howard G. Shertzer

  DOI：10.1016/s0040-4020(01)81911-6

  日期：1993.1

  The Fischer reaction between indanones and certain alkoxyarylhydrazines fails; the indanones are returned unreacted and the arylhydrazines are converted into the corresponding alkoxy-2-chloroarylamines and other products. A new N-amination route to arylhydrazines from the arylamines has been developed and it has been demonstrated that problems with the indolisation of alkoxyarylhydrazones can be circumvented by ring closures of their O-tosylated analogues. Some results using the Lepke synthesis of indoles are recorded.