2,3-dimethyl-6,7-methylenedioxyquinoline | 1539-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,3-dimethyl-6,7-methylenedioxyquinoline
• 英文别名: 6,7-dimethyl-[1,3]dioxolo[4,5-g]quinoline；6,7-Dimethyl-[1,3]dioxolo[4,5-g]chinolin；6,7-Dimethyl-[1,3]dioxolo[4,5-g]quinoline
• CAS: 1539-71-5
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: KSDIUIDTDGNJHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-3-methyl-4-(3,4-methylenedioxyphenyl)butan-2-one oxime 以49%的产率得到
  参考文献：
  名称：

  Kusama Hiroyuki, Yamashita Yuko, Narasaka Koichi, Chem. Lett, (1995) N 1, S 5-6

  摘要：

  DOI：

文献信息

• The Baylis–Hillman approach to quinoline derivatives
  作者：Oluwole B. Familoni、Phindile J. Klaas、Kevin A. Lobb、Vusumzi E. Pakade、Perry T. Kaye

  DOI：10.1039/b608592j

  日期：——

  Baylis-Hillman reactions of 2-nitrobenzaldehydes with various activated alkenes afford adducts that undergo reductive cyclisation to quinoline derivatives. The chemo- and regioselectivity of cyclisation appears to be influenced by the choice of both the substrate and the reagent system, and competing reactions have been observed.

  2-硝基苯甲醛与各种活化烯烃的Baylis-Hillman反应提供加合物，该加合物经过还原环化生成喹啉衍生物。环化反应的化学和区域选择性似乎受底物和试剂系统选择的影响，并且观察到竞争反应。
• Transformation of Oximes of Phenethyl Ketone Derivatives to Quinolines and Azaspirotrienones Catalyzed by Tetrabutylammonium Perrhenate and Trifluoromethanesulfonic Acid
  作者：Hiroyuki Kusama、Yuko Yamashita、Katsuya Uchiyama、Koichi Narasaka

  DOI：10.1246/bcsj.70.965

  日期：1997.5

  quinolines by the treatment with tetrabutylammonium perrhenate, trifluoromethanesulfonic acid, and chloranil in refluxing 1,2-dichloroethane. Azaspirotrienones can be synthesized from p-hydroxyphenethyl or 3-(p-hydroxyphenyl)propyl ketone oximes by applying the above method. Thus prepared azaspirotrienones are converted to quinolines by acid treatment.

  在回流的 1,2-二氯乙烷中，用四丁基高铼酸铵、三氟甲磺酸和氯苯醌处理将苯乙酮肟转化为喹啉。氮杂螺三烯酮可由对羟基苯乙基或3-(对羟基苯基)丙基酮肟采用上述方法合成。如此制备的氮杂螺三烯酮通过酸处理转化为喹啉。
• Application of Baylis–Hillman methodology in a novel synthesis of quinoline derivatives
  作者：Oluwole B. Familoni、Perry T. Kaye、Phindile J. Klaas

  DOI：10.1039/a807827k

  日期：——

  Reaction of 2-nitrobenzaldehyde with vinyl carbonyl compounds in the presence of 1,4-diazabicyclo[2.2.2]octane affords Baylis–Hillman products, catalytic reduction of which results in direct cyclisation to quinoline derivatives.

  在1,4-二氮双环[2.2.2]辛烷的存在下，2-硝基苯甲醛与乙烯基羰基化合物反应生成Baylis-Hillman产物，这些产物经催化还原后直接环化得到喹啉衍生物。
• Synthesis of Quinolines<i>via</i>Intramolecular Cyclization of Benzylacetone Oxime Derivatives Catalyzed with Tetrabutylammonium Perrhenate(VII) and Trifluoromethanesulfonic Acid
  作者：Hiroyuki Kusama、Yuko Yamashita、Koichi Narasaka

  DOI：10.1246/cl.1995.5

  日期：1995.1

  Intramolecular cyclization reaction on the nitrogen atom of benzylacetone oxime derivatives, which have electron donating group(s) on the phenyl group, proceeds by treatment with tetrabutylammonium perrhenate, trifluoromethanesulfonic acid, and 4-chloranil in refluxing 1,2-dichloroethane to afford quinoline derivatives in good yield.

  在苯基上具有给电子基团的苄基丙酮肟衍生物的氮原子上发生分子内环化反应，用高铼酸四丁基铵、三氟甲磺酸和4-氯苯醌在回流1,2-二氯乙烷中处理，得到喹啉衍生物产量良好。
• Foulds; Robinson, Journal of the Chemical Society, 1914, vol. 105, p. 1966
  作者：Foulds、Robinson

  DOI：——

  日期：——