6-(benzo[d][1,3]dioxol-5-yl)-6,7-dihydro-[1,3]dioxolo [4,5-g]quinolin-8(5H)-one | 1135112-23-0

• 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: 6-(benzo[d][1,3]dioxol-5-yl)-6,7-dihydro-[1,3]dioxolo [4,5-g]quinolin-8(5H)-one
• 英文别名: 6-(1,3-benzodioxol-5-yl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8-one；6-(1,3-Benzodioxol-5-yl)-6,7-dihydro[1,3]dioxolo[4,5-g]quinolin-8-ol；6-(1,3-benzodioxol-5-yl)-6,7-dihydro-5H-[1,3]dioxolo[4,5-g]quinolin-8-one
• CAS: 1135112-23-0
• 化学式: C₁₇H₁₃NO₅
• 分子量: 311.294
• InChiKey: IOWVMOVOGIWLFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(benzo[d][1,3]dioxol-5-yl)-6,7-dihydro-[1,3]dioxolo [4,5-g]quinolin-8(5H)-one 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 6-(1,3-Benzodioxol-5-yl)-[1,3]dioxolo[4,5-g]quinoline
  参考文献：
  名称：

  使用喹啉 4-酮作为方便的通用前体，用于杜巴胺和 Graveoline 生物碱以及多种结构类似物的无金属全合成

  摘要：

  芸香科是研究最多的植物科之一，因为从中分离出大量具有突出生物学特性的生物碱，其中包括喹啉类生物碱 Graveoline 1 和 Dubamine 2。生物碱 1 和 Dubamine 2 是最常用的合成方法。 2及其衍生物涉及环加成反应或金属催化的偶联过程，但在喹啉部分的范围和官能化方面存在一些限制。作为我们目前关于 2-氨基查耳酮合成和化学转化研究的延续，我们在这里报告了一种有效的无金属方法，通过两步全合成生物碱 1 和 2 及其具有结构多样性的类似物序列涉及分子内环化、氧化/芳构化、N-甲基化和氧化CC键过程，从二氢喹啉-4-酮开始，作为构建两类生物碱结构的共同前体。

  DOI：

  10.3390/molecules29091959
• 作为产物：
  描述：

  1-(6-amino-1,3-benzodioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 对甲苯磺酸 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 以98%的产率得到6-(benzo[d][1,3]dioxol-5-yl)-6,7-dihydro-[1,3]dioxolo [4,5-g]quinolin-8(5H)-one
  参考文献：
  名称：

  Conformational and configurational disorder in 6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8(5H)-one and 6-(1,3-benzodioxol-5-yl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8-one: a hydrogen-bonded chain of rings and π-stacked hydrogen-bonded chains

  摘要：

  In 6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8(5H)-one, C19H19NO6, (I), the six-membered heterocyclic ring adopts a conformation intermediate between envelope and half-chair forms; it is disordered over two enantiomeric configurations, with occupancies of 0.879 (3) and 0.121 (3), leading to positional disorder of the 3,4,5-trimethoxyphenyl unit. In 6-(1,3-benzodioxol-5-yl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g] quinolin-8-one, C17H13NO5, (II), the molecules are similarly disordered, with occupancies of 0.866 (4) and 0.134 (4). The molecules in (I) are linked by one three-centre N-H center dot center dot center dot(O)(2) hydrogen bond and one two-centre C-H center dot center dot center dot O hydrogen bond to form a complex chain of rings whose formation is reinforced by two independent aromatic pi-pi stacking interactions. In (II), a single N-H center dot center dot center dot O hydrogen bond links the molecules into a simple chain, and pairs of chains are linked by a single aromatic pi-pi stacking interaction.

  DOI：

  10.1107/s0108270109019556

文献信息

• Conformational and configurational disorder in 6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5<i>H</i>-1,3-dioxolo[4,5-<i>g</i>]quinolin-8(5<i>H</i>)-one and 6-(1,3-benzodioxol-5-yl)-6,7-dihydro-5<i>H</i>-1,3-dioxolo[4,5-<i>g</i>]quinolin-8-one: a hydrogen-bonded chain of rings and π-stacked hydrogen-bonded chains
  作者：Paola Cuervo、Rodrigo Abonía、Justo Cobo、Christopher Glidewell

  DOI：10.1107/s0108270109019556

  日期：2009.7.15

  In 6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8(5H)-one, C19H19NO6, (I), the six-membered heterocyclic ring adopts a conformation intermediate between envelope and half-chair forms; it is disordered over two enantiomeric configurations, with occupancies of 0.879 (3) and 0.121 (3), leading to positional disorder of the 3,4,5-trimethoxyphenyl unit. In 6-(1,3-benzodioxol-5-yl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g] quinolin-8-one, C17H13NO5, (II), the molecules are similarly disordered, with occupancies of 0.866 (4) and 0.134 (4). The molecules in (I) are linked by one three-centre N-H center dot center dot center dot(O)(2) hydrogen bond and one two-centre C-H center dot center dot center dot O hydrogen bond to form a complex chain of rings whose formation is reinforced by two independent aromatic pi-pi stacking interactions. In (II), a single N-H center dot center dot center dot O hydrogen bond links the molecules into a simple chain, and pairs of chains are linked by a single aromatic pi-pi stacking interaction.
• Using Quinolin-4-Ones as Convenient Common Precursors for a Metal-Free Total Synthesis of Both Dubamine and Graveoline Alkaloids and Diverse Structural Analogues
  作者：Rodrigo Abonia、Lorena Cabrera、Diana Arteaga、Daniel Insuasty、Jairo Quiroga、Paola Cuervo、Henry Insuasty

  DOI：10.3390/molecules29091959

  日期：——

  current studies on the synthesis and chemical transformation of 2-aminochalcones, we are reporting here an efficient metal-free approach for the total synthesis of alkaloids 1 and 2 along with their analogues with structural diversity, through a two-step sequence involving intramolecular cyclization, oxidation/aromatization, N-methylation and oxidative C-C bond processes, starting from dihydroquinolin-4-ones

  芸香科是研究最多的植物科之一，因为从中分离出大量具有突出生物学特性的生物碱，其中包括喹啉类生物碱 Graveoline 1 和 Dubamine 2。生物碱 1 和 Dubamine 2 是最常用的合成方法。 2及其衍生物涉及环加成反应或金属催化的偶联过程，但在喹啉部分的范围和官能化方面存在一些限制。作为我们目前关于 2-氨基查耳酮合成和化学转化研究的延续，我们在这里报告了一种有效的无金属方法，通过两步全合成生物碱 1 和 2 及其具有结构多样性的类似物序列涉及分子内环化、氧化/芳构化、N-甲基化和氧化CC键过程，从二氢喹啉-4-酮开始，作为构建两类生物碱结构的共同前体。