3,4-二甲氧基-6-碘苯基乙腈 | 58432-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,4-二甲氧基-6-碘苯基乙腈
• 英文名称: 2-(2-iodo-4,5-dimethoxyphenyl)acetonitrile
• CAS: 58432-84-1
• 化学式: C₁₀H₁₀INO₂
• 分子量: 303.099
• InChiKey: AJKWCXOMVYKAEI-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  379.1±42.0 °C(Predicted)
• 密度：
  1.632±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基-6-碘苯基乙腈 在 盐酸 、 sodium tetrahydroborate 、 硼烷四氢呋喃络合物 、 异丙基氯化镁 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 23.5h， 生成 15,16-dimethoxy-cis-erythrinane
  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：

  3,4-二甲氧基苯乙腈 在 一氯化碘 、 溶剂黄146 作用下， 以72%的产率得到3,4-二甲氧基-6-碘苯基乙腈
  参考文献：
  名称：

  A Ring-Closing Metathesis-Based Approach to the Synthesis of (+)-Tetrabenazine

  摘要：

  A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-alpha-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.

  DOI：

  10.1021/ol301612q

文献信息

• Carbopalladation of Nitriles:  Synthesis of 3,4-Disubstituted 2-Aminonaphthalenes and 1,3-Benzoxazine Derivatives by the Palladium-Catalyzed Annulation of Alkynes by (2-Iodophenyl)acetonitrile
  作者：Qingping Tian、Alexandre A. Pletnev、Richard C. Larock

  DOI：10.1021/jo026229+

  日期：2003.1.1

  studied. The annulation of certain hindered propargylic alcohols affords 1,3-benzoxazine derivatives, rather than the expected 2-aminonaphthalenes. The involvement of trialkylamine bases in the formation of these heterocyclic compounds has been established. A proposed mechanism for the synthesis of 1,3-benzoxazine derivatives involves the formation of the expected 2-amino-3-(1-hydroxyalkyl)naphthalenes

  氰基的分子内碳氢合被用于合成3，4-二取代的2-氨基萘。（2-碘苯基）乙腈与各种内部炔烃反应以高收率和良好的区域选择性提供2-氨基萘。已经研究了该方法的范围和局限性，该过程是通过分子内将乙烯基钯物质加到氰基的三键上而进行的。某些受阻炔丙基醇的环化可提供1,3-苯并恶嗪衍生物，而不是预期的2-氨基萘。已经确定三烷基胺碱参与这些杂环化合物的形成。拟议的1,3-苯并恶嗪衍生物合成机理涉及预期的2-氨基-3-（1-羟烷基）萘的形成，
• Palladium(II)-Catalyzed Annulation of Alkynes with 2-(Cyanomethyl)phenylboronates Leading to 3,4-Disubstituted 2-Naphthalenamines
  作者：Hirokazu Tsukamoto、Taishi Ikeda、Takayuki Doi

  DOI：10.1021/acs.joc.5b02378

  日期：2016.3.4

  palladium(II) complexes catalyze the annulation of internal alkynes with 2-(cyanomethyl)phenylboronates to provide 3,4-disubstituted-2-naphthalenamines in good yields. The annulation reaction proceeds under mild and neutral conditions and requires methanol as an essential solvent. In addition to symmetrical alkynes, unsymmetrical alkynes substituted by aryl, alkyl, and alkynyl groups participate in

  1,2-双（二苯基膦基）乙烷（dppe）连接的钯（II）配合物催化内部炔烃与2-（氰基甲基）苯基硼酸酯的环化反应，从而以良好的收率提供3,4-二取代的-2-萘胺。环化反应在温和和中性条件下进行，需要甲醇作为必要溶剂。除对称炔烃外，被芳基，烷基和炔基取代的不对称炔烃也参与环化反应，得到相应的带有吸电子sp 2的2-萘胺。-和sp-carbons优先位于C-3位置。在硼酸酯中包括在氰基甲基部分上的烷基或烷氧基和在苯环上的卤素原子的取代基与反应条件相容。通过用硼酸酯和炔烃插入钯（II）配合物进行金属转移，然后将生成的烯基钯（II）亲核加成到分子内氰基中来进行环化。化学计量反应表明，甲醇溶剂对于重金属化和催化剂再生均有效。
• Palladium(ii)-catalyzed synthesis of functionalized indenones via oxidation and cyclization of 2-(2-arylethynylphenyl)acetonitriles
  作者：Xuxing Chen、Qian He、Yuyuan Xie、Chunhao Yang

  DOI：10.1039/c3ob40103k

  日期：——

  A one-pot two-step synthesis of versatile indenones has been developed. This palladium(II)-catalyzed transformation involves generation and condensation of ortho-functionalized 1,2-benzils from 2-(2-arylethynylphenyl)acetonitriles using Ph2SO as the oxidant. The resulting 3-cyanoindenones can be converted to various valuable molecules.

  已经开发了一种一锅两步合成多功能烯酮的工艺。该钯(II)催化的转化过程涉及使用Ph2SO作为氧化剂，从2-(2-芳基乙炔基苯基)乙腈生成并缩合邻位功能化的1,2-苯基酮。所得到的3-氰基烯酮可以转化为各种有价值的分子。
• A Microwave-Assisted Domino Benzannulation Reaction towards Functionalized Naphthalenes, Quinolines, and Isoquinolines
  作者：Yuqin Wang、Cun Tan、Xiaofei Zhang、Qian He、Yuyuan Xie、Chunhao Yang

  DOI：10.1002/ejoc.201201061

  日期：2012.10.9

  zed domino reaction was developed to yield functionalized naphthalenes, quinolines, and isoquinolines. The reactions of various substituted 1-phenylprop-2-yn-1-ols containing electron-donating (EDG) and electron-withdrawing (EWG) groups and 1-heteroarylprop-2-yn-1-ols worked well with this procedure. Both electron-rich and -deficient aryl halides were satisfactory substrates for this reaction. This

  开发了一种有效的钯/铜催化的多米诺反应，以产生功能化的萘、喹啉和异喹啉。含有给电子 (EDG) 和吸电子 (EWG) 基团的各种取代的 1-苯基丙-2-yn-1-醇与 1-杂芳基丙-2-yn-1-醇的反应适用于该程序。富电子和缺电子的芳基卤化物都是该反应的令人满意的底物。这种多米诺苯环化过程涉及 Sonogashira 交叉偶联反应，然后异构化为查耳酮，最后是分子内缩合反应。
• Synthesis of Substituted Benzo[<i>b</i>]thiophenes via Base-Promoted Domino Condensation–Intramolecular C–S Bond Formation
  作者：Yogendra Kumar、Hiriyakkanavar Ila

  DOI：10.1021/acs.orglett.1c00085

  日期：2021.3.5

  A novel synthesis of 2,3-substituted benzothiophenes is reported, involving a tandem base-mediated condensation of o-iodoarylacetonitriles/acetates/ketones with (hetero)aryldithioesters and an intramolecular C–S bond formation. The reaction affords diversely substituted benzothiophenes and heterofused thiophenes in excellent yields.

  据报道，有一种新颖的2，3-取代的苯并噻吩的合成方法，涉及到邻位碘代芳基乙腈/乙酸酯/酮与（杂）芳基二硫代酸酯的串联碱基介导的缩合反应以及分子内C-S键的形成。该反应以优异的产率提供了各种取代的苯并噻吩和杂稠的噻吩。