6-formylbenzo[1,3]dioxole-5-carbonitrile | 1970-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 6-formylbenzo[1,3]dioxole-5-carbonitrile
• 英文别名: 6-Cyano-1,3-benzodioxol-5-carboxaldehyde；6-formyl-1,3-benzodioxole-5-carbonitrile
• CAS: 1970-22-5
• 化学式: C₉H₅NO₃
• 分子量: 175.144
• InChiKey: MZAJIUMHVIXGAR-UHFFFAOYSA-N

物化性质

• 熔点：
  160-162 °C(Solv: water (7732-18-5))
• 沸点：
  358.4±42.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-formylbenzo[1,3]dioxole-5-carbonitrile 在 sodium tetrahydroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 6-methoxymethoxymethylbenzo[1,3]dioxole-5-carbonitrile
  参考文献：
  名称：

  锂化甲苯酰胺-苄腈环加成反应可轻松合成苯并[ c ]菲啶生物碱：氧硝啶和氧山桂碱

  摘要：

  使用甲苯酰胺-苄腈环加成反应，通过六个步骤，由易于获得的起始苯甲腈5和甲苯酰胺6合成苯并[ c ]菲啶生物碱氧硝啶和氧山桂碱。该方法是如此高效，以至于它是制备完全芳构化的苯并[ c ]菲啶化合物的更有用的方法。

  DOI：

  10.1016/j.tetlet.2004.02.031
• 作为产物：
  描述：

  6-溴-3,4-亚甲基二氧苯甲醛 在 盐酸 、 对甲苯磺酸 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.25h， 生成 6-formylbenzo[1,3]dioxole-5-carbonitrile
  参考文献：
  名称：

  Novel 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones: Synthesis and antileishmanial effects against Leishmania amazonensis

  摘要：

  A series of eleven 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones (16-27) was synthesised as part of a study to search for potential new drugs with a leishmanicidal effect. The thiosemicarbazones, ten of which are new compounds, were prepared in good yields (85-98%) by the reaction of 3,4-methylenedioxyde-6-benzaldehydes (6-X-piperonal), previously synthesised for this work by several methodologies, and thiosemicarbazide in ethanol with a few drops of H2SO4. These compounds were evaluated against Leishmania amazonensis promastigotes, and derivatives where X = I (22) and X = CN (23) moieties showed impressive results, having IC50 = 20.74 mu M and 16.40 mu M, respectively. The intracellular amastigotes assays showed IC50 = 22.00 mu M (22) and 17.00 mu M (23), and selectivity index >5.7 and >7.4, respectively, with a lower toxicity compared to pentamidine (positive control, SI = 4.5). The results obtained from the preliminary QSAR study indicated the hydrophobicity (log P) as a fundamental parameter for the 2D-QSAR linear model. A molecular docking study demonstrated that both compounds interact with flavin mononucleotide (FMN), important binding site of NO synthase. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.009

文献信息

• Chiral imidate–ferrocenylphosphanes: synthesis and application as P,N-ligands in iridium(i)-catalyzed hydrogenation of unfunctionalized and poorly functionalized olefins
  作者：Katrien Bert、Timothy Noël、Wim Kimpe、Jan L. Goeman、Johan Van der Eycken

  DOI：10.1039/c2ob25871d

  日期：——

  A small library of chiral imidate–ferrocenylphosphane ligands was efficiently synthesized (8 examples) and evaluated in the iridium(I)-catalyzed hydrogenation of unfunctionalized and poorly functionalized olefins. These catalysts perform very well in a range of examples (yields and ee's up to 100%).

  高效合成了一小类手性咪唑酰亚胺–铁烯基膦配体（8个例子），并在铱(I)催化的未功能化和功能化较差的烯烃的加氢反应中进行了评估。这些催化剂在一系列的例子中表现非常良好（产率和对映体过量高达100%）。
• CYCLIC IMIDATE LIGANDS
  申请人：Noël Timothy

  公开号：US20120077989A1

  公开（公告）日：2012-03-29

  The present invention relates to a use of a cyclic imidate as a ligand for catalysis in which the ligand contains sub-structure (Y) as a minimal structural motive, wherein the carbon atoms and the nitrogen atom can be optionally substituted by a chemical substituent.

  本发明涉及将环戊二酰亚胺用作催化剂中的配体的用途，其中该配体包含亚结构（Y）作为最小结构动机，其中碳原子和氮原子可以选择性地被化学取代基取代。
• Total Synthesis of Oxyfagaronine, Phenolic Benzo[c]phenanthridine and General Synthetic Way of 2,3,7,8- and 2,3,8,9-Tetrasubstituted Benzo[c]phenanthridine Alkaloids
  作者：Thanh Nguyen Le、Won-Jea Cho

  DOI：10.1248/cpb.54.476

  日期：——

  Benzo[c]phenanthridine alkaloids such as oxynitidine, oxysanguinarine, oxyavicine and phenolic oxyfagaronine were synthesized from easily available starting benzonitriles 5 and toluamides 6 using a lithiated toluamide-benzonitrile cycloaddition reaction. The coupling reaction provided 3-arylisoquinolinones that were transformed to the benzo[c]phenanthridones. This method is highly efficient and could

  使用锂化甲苯酰胺-苄腈环加成反应，由易得的起始苯甲腈5和甲苯酰胺6合成苯并[c]菲啶生物碱，例如氧硝啶，氧山桂碱，氧鸟嘌呤和酚氧法加宁。偶联反应提供了3-芳基异喹啉酮，其被转化为苯并[c]菲蒽酮。该方法是高效的，并且可用于以克为单位制备各种取代的芳族苯并[c]菲啶化合物。
• A Versatile Total Synthesis of Benzo[<i>c</i>]phenanthridine and Protoberberine Alkaloids Using Lithiated Toluamide−Benzonitrile Cycloaddition
  作者：Thanh Nguyen Le、Seong Gyoung Gang、Won-Jea Cho

  DOI：10.1021/jo035836+

  日期：2004.4.1

  A new versatile synthesis of benzo[c]phenanthridine and protoberberine alkaloids using lithiated toluamide−benzonitrile cycloaddition was carried out. The coupling reaction between benzonitrile 6 with o-toluamides (8a−c) afforded 3-arylisoquinolines (9a−c) that were transformed to the protoberberines (11a−c) or benzo[c]phenanthridines (14a−c). These compounds were synthesized by ring closure of the

  利用锂化的甲苯胺-苄腈环加成法进行了苯并[ c ]菲啶和原小ber碱生物碱的新型通用合成。苄腈6与邻甲苯甲酰胺（8a - c）之间的偶联反应提供了3-芳基异喹啉（9a - c），该3-芳基异喹啉（9a - c）转化为原小ber碱（11a - c）或苯并[ c ]菲啶（14a - c）。这些化合物是通过在3-芳基异喹啉酮（9a - c）。合成了几种取代的苯并[ c ]菲啶生物碱，例如氧山桂碱，氧鸟嘌呤和氧可尼丁，以及原小ber碱，例如8-氧代黄嘌呤，8-氧代伪小ber碱和8-氧代葡多酚。
• 一种1-氨基多取代异喹啉类化合物的合成方法
  申请人：兰州大学

  公开号：CN110627720A

  公开（公告）日：2019-12-31

  本发明属于有机合成技术领域,具体涉及一种1‑氨基多取代异喹啉类化合物的合成方法，其反应通式如下：本发明由多取代苯腈和取代异腈化合物在催化剂和碱的作用下，发生环化反应合成1‑氨基多取代异喹啉类化合物。该方法所用的起始原料易得，操作简单，反应条件温和，催化剂廉价，能减少资金和劳动力的投入量，为1‑氨基多取代异喹啉衍生物提供一种快捷高效的制备方法。