丙基异氰化物 | 627-36-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 丙基异氰化物
• 英文名称: n-propyl isocyanide
• 英文别名: 1-isocyanopropane；n-Propylisocyanid
• CAS: 627-36-1
• 化学式: C₄H₇N
• 分子量: 69.1063
• InChiKey: FFDKYFGBIQQMSR-UHFFFAOYSA-N

物化性质

• 沸点：
  117.85°C (estimate)
• 密度：
  0.7526

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  4.4
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  水合氯醛 、 丙基异氰化物 在 乙醚 作用下， 生成 3,3,3-trichloro-2-hydroxy-propionic acid propylamide
  参考文献：
  名称：

  Passerini, Gazzetta Chimica Italiana, 1926, vol. 56, p. 828

  摘要：

  DOI：
• 作为产物：
  描述：

  N-丙基甲酰胺 在 对甲苯磺酰氯 作用下， 以 喹啉 为溶剂， 生成 丙基异氰化物
  参考文献：
  名称：

  The question of tautomerism of alkylnitrile and isonitrile radical cations

  摘要：

  AbstractThe isomeric pairs [CH3CN]+˙ and [CH2CNH]+˙ and [CH3NC]+˙ and [CH2NCH]+˙ have been established as stable, noninterconverting structures. The conclusion derives from studies of collision induced decomposition spectra. The same conclusion pertains for the ions [CH3CH2CN]+˙ and [CH3CHCNH]+˙, and for [NCCH2CH2CN]+˙, [HNCCHCH2CN]+˙ and [HNCCHCHCNH]+˙. The energy barrier of a [1,3]‐hydrogen shift, a possible isomerization mechanism, is determined to be at least 163 kJ mol−1 for the [CH3CN]+˙ and [CH2CNH]+˙ pair, and the barrier may be as high as 318 kJ mol−1. The C3H5N and C4H4N2 radical cations decompose before they can be activated with 318 kJ mol−1 of internal energy.

  DOI：

  10.1002/oms.1210171005

文献信息

• An efficient procedure for the synthesis of functionalized 3,4-dihydro-2H-pyrans via catalytic multicomponent reaction
  作者：Alireza Samzadeh-Kermani、Sajjad Ataeifar

  DOI：10.1007/s00706-017-2065-y

  日期：2018.1

  with reactive nitrilium ion derived from the reaction of isocyanides and oxiranes in the presence of lithium salts in PEG-400. The reaction was successfully utilized to synthesize 3,4-dihydro-2H-pyrans in accordance with a simple and environmentally benign procedure. The optimized reaction conditions allowed the selective synthesis of the highly functionalized 3,4-dihydro-2H-pyrans from the commercially

  摘要在该转化中，在PEG-400中存在锂盐的情况下，使丙二腈的共轭碱与衍生自异氰化物和环氧乙烷的反应的反应性氮离子反应。根据简单且环境友好的方法，该反应成功地用于合成3，4-二氢-2 H-吡喃。优化的反应条件允许以可接受的收率从市售起始原料选择性合成高度官能化的3，4-二氢-2 H-吡喃。 图形概要
• 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。
• Isocyanide-based multicomponent reaction for the formation of 1,3-oxathiolane-2-imine derivatives
  作者：Alireza Samzadeh-Kermani、Samira Zamenraz

  DOI：10.1007/s00706-017-1939-3

  日期：2017.10

  AbstractThe adduct of isocyanide and elemental sulfur has been employed as the isothiocyanate source in reaction with oxirane to form 1,3-oxathiolane-2-imine derivatives. The optimum conditions are developed using HMPA at 55 °C for 12 h. Various isocyanides and oxiranes were tolerated under the optimum conditions. Graphical abstract

  摘要异氰化物和元素硫的加合物已被用作与环氧乙烷反应形成1，3-氧杂硫杂环戊烷-2-亚胺衍生物的异硫氰酸酯源。使用HMPA在55°C的条件下开发最佳条件12 h。在最佳条件下可以耐受各种异氰酸酯和环氧乙烷。 图形概要
• Monomere carbiminoborane
  作者：Ulrich Sicker、Anton Meller、Walter Maringgele

  DOI：10.1016/s0022-328x(00)92886-9

  日期：1982.5

  A series of monomeric carbiminoboranes is obtained by treatment of isonitriles with organolithium compounds and subsequent treatment with amino-haloboranes. By an analogous reaction carbiminosilanes can be prepared, having a hydrogen atom in α-position to the imine group. Carbiminosilanes react with aminohaloboranes to give trimethylsilylenaminoboranes and in the case of 1-methyl-5-phenyl-2-trimet

  通过用有机锂化合物处理异腈并随后用氨基卤硼烷处理，可获得一系列单体碳氨硼烷。通过类似的反应，可以制备碳氨基硅烷，其在亚胺基的α位具有氢原子。碳氨基硅烷与氨基卤硼烷反应生成三甲基甲硅烷基氨基硼烷，在1-甲基-5-苯基-2-三甲基甲硅烷基-2-咪唑啉的情况下，SiC键断裂。所述化合物通过分析和光谱表征（IR； NMR：1 H，11 B，29 Si； MS）。
• Formation of peptide bonds in the presence of isonitriles
  申请人：Ajinomoto Co., Inc.

  公开号：US03933783A1

  公开（公告）日：1976-01-20

  Amino acids having masked amino groups react with amino acids having masked carboxyl groups to form peptide derivatives in good yields if the reaction medium contains an isonitrile. Isonitriles also are effective in causing condensation of amino acids having masked amino groups with compounds having active hydroxyl groups to the corresponding amino acid esters. The yields of the first-mentioned reaction are enhanced if the reaction mixture additionally contains one of the compounds having active hydroxyl groups. Both the peptide derivatives and the amino acid esters of the compounds having active hydroxyl groups are useful for peptide synthesis.

  具有掩蔽氨基的氨基酸与具有掩蔽羧基的氨基酸在含有异腈的反应介质中反应，可以高产率地形成肽衍生物。异腈还能有效地导致具有掩蔽氨基的氨基酸与具有活性羟基的化合物发生缩合反应，形成相应的氨基酸酯。如果反应混合物中另外含有一种具有活性羟基的化合物，则第一种反应的产率会提高。这些肽衍生物和具有活性羟基化合物的氨基酸酯对肽合成非常有用。

表征谱图