2-(2-iodo-4,5-methylenedioxyphenyl)acetonitrile | 809233-22-5

• 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: 2-(2-iodo-4,5-methylenedioxyphenyl)acetonitrile
• 英文别名: 2-(2-iodo-3,4-methylenedioxyphenyl)acetonitrile；2-(6-iodo-1,3-benzodioxol-5-yl)acetonitrile
• CAS: 809233-22-5
• 化学式: C₉H₆INO₂
• 分子量: 287.057
• InChiKey: KGJOGTPHOCAIPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42.25
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-iodo-4,5-methylenedioxyphenyl)acetonitrile 在 硼烷四氢呋喃络合物 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以83%的产率得到2-(2-iodo-4,5-methylenedioxyphenyl)ethylamine
  参考文献：
  名称：

  An Improved Stereocontrolled Route to cis-Erythrinanes by Combined Intramolecular Strecker and Bruylants Reaction

  摘要：

  Condensation of (2-iodophenyl)ethylamines with cyclohexanoylacetaldehyde provided the corresponding aldimines which were reduced yielding secondary phenethylcyclohexanoylethylamines. These in turn were appropriate intermediates to prepare several erythrinanes by a sequential intramolecular Strecker and intramolecular Bruylants reaction. In contrast, the C-ring homologue schelhammeranes were not available on this route.

  DOI：

  10.1007/s00706-004-0184-8
• 作为产物：
  描述：

  1,3-苯并二氧杂环戊烯-5-乙腈 在 碘 、 silver trifluoroacetate 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到2-(2-iodo-4,5-methylenedioxyphenyl)acetonitrile
  参考文献：
  名称：

  Palladium-Catalyzed Carboxamidation Reaction and Aldol Condensation Reaction Cascade: A Facile Approach to Ring-Fused Isoquinolinones

  摘要：

  Palladium-catalyzed carboxamidation reaction and aldol condensation reaction cascade are very useful for the synthesis of various ABC ring substituted fused isoquinolinones.

  DOI：

  10.1021/ol802067y

文献信息

• Synthesis of Ring-Fused Oxazolo- and Pyrazoloisoquinolinones by a One-Pot Pd-Catalyzed Carboxamidation and Aldol-Type Condensation Cascade Process
  作者：Gagan Chouhan、Howard Alper

  DOI：10.1021/jo9010574

  日期：2009.8.21

  three-component cascade process is described for the synthesis of ring-fused oxazolo- and pyrazoloisoquinolinones by a one-pot carboxamidation/aldol-type condensation reaction. The cascade process involves Pd-catalyzed carboxamidation of an aryl halide/active methylene compound with oxazolidinone or pyrazolidinone, and subsequent intramolecular base-catalyzed cyclization/dehydration through an aldol-type

  描述了通过单锅羧酰胺化/醛醇缩合反应合成环稠合的恶唑啉和吡唑异喹啉酮的三组分级联方法。级联过程涉及芳基卤化物/活性亚甲基化合物与恶唑烷酮或吡唑烷酮的钯催化羧酰胺化，以及随后的分子内碱催化的醛醇缩合环化/脱水，以产生环稠合的恶唑啉代和吡唑并异喹啉酮。这种方法为这些重要的含氮杂环类化合物提供了一种简单的一步方法，并且可以耐受各种官能团，包括酯，腈，甲氧基和卤化物。
• Synthesis of 1,2,3-Fused Indole Polyheterocycles by Copper-Catalyzed Cascade Reaction
  作者：Veerababurao Kavala、Zonghan Yang、Ashok Konala、Tang-Hao Yang、Chun-Wei Kuo、Jian-Yao Ruan、Ching-Fa Yao

  DOI：10.1002/ejoc.201701618

  日期：2018.3.14

  A copper‐catalyzed cascade reaction between 2‐iodobenzamide and 2‐iodobenzyl cyanide has been developed. The one‐pot protocol provides access to a wide range of 1,2,3‐fused indole polyheterocycles in good yields within a short period of time.

  已经开发了2-碘代苯甲酰胺和2-碘代苄基氰化物之间的铜催化级联反应。单锅协议可在短时间内以高收率访问各种1,2,3稠合的吲哚多杂环。
• Synthesis of Benzopyridoindolone Derivatives via a One-Pot Copper Catalyzed Tandem Reaction of 2-Iodobenzamide Derivatives and 2-Iodobenzylcyanides
  作者：Veerababurao Kavala、Zonghan Yang、Ashok Konala、Chia-Yu Huang、Chun-Wei Kuo、Ching-Fa Yao

  DOI：10.1021/acs.joc.7b00862

  日期：2017.7.21

  An efficient approach for the synthesis of benzo-fused pyridoindolone derivatives via a one-pot copper catalyzed tandem reaction of 2-iodobenzamides with 2-iodobenzylcyanides has been developed. Using this protocol, benzo-fused pyridoindolone derivatives are obtained in high yields in a relatively short period of time under mild reaction conditions. To the best of our knowledge, this is the first approach

  已经开发了一种通过一锅铜催化的2-碘代苯甲酰胺与2-碘苄基氰化物的串联反应合成苯并稠合的吡啶并吲哚酮衍生物的有效方法。使用该方案，在温和的反应条件下，可以在相对较短的时间内以高收率获得苯并稠合的吡啶并吲哚酮衍生物。据我们所知，这是第一个可以合成游离吲哚NH苯并稠合吡啶并吲哚酮的方法。同样，在反应过程中同时构造了吲哚和吡啶酮核。该方法显示出良好的官能团耐受性，并可以合成噻吩稠合的吡啶并吲哚酮和稠合的吲哚苯并萘并吡啶酮衍生物。