己基异氰化物 | 15586-23-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 己基异氰化物
• 中文别名: N-次甲基己烷-1-铵
• 英文名称: n-hexyl isocyanide
• 英文别名: n-hexyl isonitrile；Hexyl isocyanide；1-isocyanohexane
• CAS: 15586-23-9
• 化学式: C₇H₁₃N
• mdl: MFCD00065203
• 分子量: 111.187
• InChiKey: AWJCOFYWVBNFET-UHFFFAOYSA-N

物化性质

• 沸点：
  168-169 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  4.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  己基异氰化物 在 selenium 、 sodium azide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 5-[(3,5-Dinitrobenzyl)selanyl]-1-hexyl-1H-tetrazole
  参考文献：
  名称：

  One-pot synthesis of 1-substituted-5-alkylselanyl-1 H -tetrazoles from isoselenocyanates: unexpected formation of N -alkyl- N -arylcyanamides and ( Z )- Se -alkyl- N -cyano- N , N′ -diarylisoselenoureas

  摘要：

  1-Substituted-5-alkylsulfanyl-1H-tetrazoles are well known class of organic substances with various applications in medicinal chemistry or photographic industry. Their selenium analogues, 1-substituted-5-alkylselanyl-1H-tetrazoles are, however, much less explored because of the lack of suitable methods for their preparation. In this work we investigated the synthesis of 1-alkyl/aryl-5-alkylselanyl-1H-tetrazoles from synthetically available alkyl/arylisoselenocyanates. One-pot reactions of arylisoseleno cyanates with sodium azide and alkylating agent led to the target 5-alkylselanyl-1-aryl-1H-tetrazoles but also to interesting side products, namely N-alkyl-N-arylcyanamides and (2)-Se-alkyl-N-cyano-N,N'-diarylisoselenoureas. Nevertheless, when alkylisoselenocyanates were utilized as the substrates, the reactions led exclusively to the formation of 1-alkyl-5-alkylselanyl-1H-tetrazoles in good yields. This simple one-pot procedure brings new possibilities for the preparation of variously substituted selenium compounds. It also opens the way to further investigations of selenium isosteres of the widely utilized 5-thiotetrazole moiety in biomedical applications. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.103
• 作为产物：
  描述：

  异硫氰酸己酯 在 3-polystyrylmethyl-2-phenyl[1,3,2]oxazaphospholidine 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以85%的产率得到己基异氰化物
  参考文献：
  名称：

  A polymer-Supported [1,3,2]Oxazaphospholidine for the conversion of isothiocyanates to isocyanides and Their subsequent use in an ugi reaction

  摘要：

  The design and synthesis of a new polymer supported reagent for the clean conversion of isothiocyanates to isocyanides under microwave conditions was accomplished. The structurally diverse isocyanides generated were used in an Ugi 3CC, allowing the rapid generation of 2-isoindolinone-7-carboxamide analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00269-x

文献信息

• Multicomponent Reaction to Construct Spirocyclic Oxindoles with a Michael (Triple Michael)/Cyclization Cascade Sequence as the Key Step
  作者：Jian Li、Ning Wang、Chunju Li、Xueshun Jia

  DOI：10.1002/chem.201104071

  日期：2012.7.27

  new strategy to access highly unusual tricyclic oxindoles. From a synthetic point of view, this protocol is very interesting considering the high level of complexity reached in one step. The mechanism is thought to proceed by a triple Michael/cyclization process by using allenoate as a three carbon atom component (3 C). Furthermore, multicomponent reaction with γ‐substituted allenoate also results in

  公开了具有容易获得的异氰酸酯，脲基酸酯和异亚丙基丙二腈的多组分环加成物。该反应不需要任何催化剂的帮助，使得能够以优异的区域选择性有效地合成螺环恶吲哚。还充分探讨了与2,3-丁二烯酸乙酯和各种结构不同的α-和γ-取代的烯醇酸酯的反应。值得注意的是，我们已经表明，通常的三组分过程可以在存在水的情况下进一步发展为史无前例的四组分环加成反应，这提供了一种新的策略来获得高度不寻常的三环羟吲哚。从综合的角度来看，考虑到一步就可以达到很高的复杂性，该协议非常有趣。该机理被认为是通过使用烯丙酸酯作为三个碳原子组分（3 C）通过三重迈克尔/环化过程进行的。此外，与γ-取代的脲基甲酸酯的多组分反应也导致非常有趣的转化。在这种情况下，总是观察到异亚丙基丙二腈的“CC”双键和脲基酸酯的“CC”双键之一的不寻常断裂。
• Synthesis and structure–activity relationship of α-keto amides as enterovirus 71 3C protease inhibitors
  作者：Debin Zeng、Yuying Ma、Rui Zhang、Quandeng Nie、Zhengjie Cui、Yaxin Wang、Luqing Shang、Zheng Yin

  DOI：10.1016/j.bmcl.2016.02.039

  日期：2016.4

  α-Keto amide derivatives as enterovirus 71 (EV71) 3C protease (3Cpro) inhibitors have been synthesized and assayed for their biochemical and antiviral activities. structure–activity relationship (SAR) study indicated that small moieties were primarily tolerated at P1′ and the introduction of para-fluoro benzyl at P2 notably improved the potency of inhibitor. Inhibitors 8v, 8w and 8x exhibited satisfactory

  已经合成了作为肠病毒71（EV71）3C蛋白酶（3C pro）抑制剂的α-酮酰胺衍生物，并对其生化和抗病毒活性进行了测定。结构-活性关系（SAR）研究表明，在P1'处主要耐受小部分，在P2处引入对氟苄基可显着提高抑制剂的效力。抑制剂8v，8w和8x表现出令人满意的活性（IC 50分别 为1.32±0.26μM，1.88±0.35μM和1.52±0.31μM）和良好的CC 50值（CC 50  > 100μM）。α-酮酰胺可能是EV71 3C pro抑制剂的弹头的不错选择。
• C–H functionalization enabled stereoselective Ugi-azide reaction to α-tetrazolyl alicyclic amines
  作者：Surajit Haldar、Subhajit Saha、Sumana Mandal、Chandan K. Jana

  DOI：10.1039/c8gc01544a

  日期：——

  novel reaction produces α-tetrazolyl N-heterocycles directly from N-heterocycles without involving pre-functionalization/pre-oxidation steps. Importantly, the stereoselective reaction involving chiral amines or chiral isocyanides allowed the expeditious syntheses of nucleoside analogs and α-tetrazolyl pyrrolidine in enantioenriched form.

  据报道，前所未有的立体选择性C（sp 3）-H功能化使Ugi-叠氮化物（CH-Ugi-叠氮化物）反应成为可能。该新颖的反应直接从N-杂环产生α-四唑基N-杂环，而无需涉及预功能化/预氧化步骤。重要的是，涉及手性胺或手性异氰化物的立体选择性反应允许对映体富集形式的核苷类似物和α-四唑基吡咯烷的快速合成。
• Synthesis of diphenylamine macrocycles and their anti-inflammatory effects
  作者：Alejandra Chávez-Riveros、Eduardo Hernández-Vázquez、Antonio Nieto-Camacho、Teresa Ramírez-Apan、Luis D. Miranda

  DOI：10.1039/c8ob03121e

  日期：——

  A collection of fourteen diphenylamine macrocyclic derivatives containing a peptide chain with different substituents was synthesized using a protocol of two Ugi four component reactions (Ugi-4CR) and a Buchwald–Hartwig macrocyclization. Their anti-inflammatory effects were assayed with an ear edema model using 12-O-tetradecanoylphorbol-13-acetate, while the activity of myeloperoxidase was determined

  使用两个Ugi四组分反应（Ugi-4CR）和Buchwald-Hartwig大环化的方案，合成了十四个二苯胺大环衍生物，其中含有一条具有不同取代基的肽链。使用12 - O-十四烷酰佛波醇-13-乙酸酯通过耳部水肿模型测定其抗炎作用，同时测定髓过氧化物酶的活性以评估白细胞浸润指数。化合物5e的ID 50为每只耳朵0.18μM，效力高于参考药物消炎痛和塞来昔布（分别为0.24和0.91μM每只耳朵）。此外，在两个健康细胞系中测定了大环化合物的细胞毒性，显示出较低的毒性百分比。
• Palladium-catalyzed direct coupling of 2-vinylanilines and isocyanides: an efficient synthesis of 2-aminoquinolines
  作者：Lijie Wang、Jamie Ferguson、Fanlong Zeng

  DOI：10.1039/c5ob01659b

  日期：——

  A variety of 2-aminoquinolines were prepared in good to excellent yields.

  一系列2-氨基喹啉以良好至优异的产率制备完成。