5-碘-2-噻吩甲腈 | 18945-81-8

• 物质功能分类: 医药中间体 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-碘-2-噻吩甲腈
• 英文名称: 5-iodothiophene-2-carbonitrile
• CAS: 18945-81-8
• 化学式: C₅H₂INS
• 分子量: 235.048
• InChiKey: DCTRQPYCGCNWBN-UHFFFAOYSA-N

物化性质

• 密度：
  2.14

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  2-(二甲基氨基)噻吩 、 5-碘-2-噻吩甲腈 在 bis-triphenylphosphine-palladium(II) chloride 正丁基锂 、 三甲基氯化锡 作用下， 生成 α-dimethylamino,α'-cyano-bithiophene
  参考文献：
  名称：

  Synthesis and Solvatochromic Properties of Donor-Acceptor-Substituted Oligothiophenes

  摘要：

  The Pd-catalyzed cross coupling reaction of electron donor-substituted thiophenes 1 with electron acceptor-substituted halothiophenes 2,10 via organozinc intermediates or organotin compounds 5 to give bi-, ter-, and quaterthiophenes 3, 4, 6, 8, 12, 13, and 14 is described. (Dimethylamino)-bithiophenes 8 with acceptor groups of varying reactivity were prepared via 5d in 60-80% yield, whereas bithiophenes 6d,e were obtained as a mixture with phenylthiophenes 7d,e. Symmetrical substituted byproducts 11 were formed in the conversion of 1b with bromothiophenes 10 via organozinc compounds yielding oligothiophenes 6b and 12. The ter- and quaterthiophenes 13 and 14 were isolated in about 50-70% yield. The electronic interactions between donor and acceptor end groups in the conjugated bithiophenes 3, 4, and 8 are expressed in the intensive and markedly solvatochromic CT transitions. The solvatochromic behavior of 3, 4, and 8 was determined by linear regression analyses of absorption maxima in 11 solvents, whereby bithiophene 3d was found to be a very appropriate indicator dye whose absorption wavenumbers ($) over bar nu(max)(3d) in aliphatic and dipolar aprotic and-on consideration of the polarizability correction term d delta-in aromatic and chlorinated solvents excellently correlate with the pi* values defined by Kamlet and Taft.

  DOI：

  10.1021/jo00112a032
• 作为产物：
  描述：

  2-氰基噻吩 在 碘 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以71%的产率得到5-碘-2-噻吩甲腈
  参考文献：
  名称：

  Bis-(trifluoroacetoxy)iodobenzene — iodine system: An efficient and selective reagent for iodination of thiophene derivatives

  摘要：

  DOI：

  10.1016/0040-4039(95)00876-e

文献信息

• Systematic Investigation of the Scope of Transannular C–H Heteroarylation of Cyclic Secondary Amines for Synthetic Application in Medicinal Chemistry
  作者：Zhe Li、Michael Dechantsreiter、Sivaraman Dandapani

  DOI：10.1021/acs.joc.0c00870

  日期：2020.5.15

  Transannular C-H heteroarylation of amines provides rapid access to complex scaffolds that are otherwise difficult to synthesize. Wide adaptation of this emerging reaction for medicinal chemistry requires a broad understanding of substrate scope and more robust experimental conditions. In this article, we report a new ligand to promote the transannular reaction of a range of fused- and bridged-bicyclic

  胺的跨环CH杂芳基化可快速进入复杂的骨架，而这些骨架否则很难合成。这种新兴反应对药物化学的广泛适应要求对底物范围和更稳定的实验条件有广泛的了解。在本文中，我们报告了一种新的配体，以促进一系列稠合和桥联双环仲胺与一系列杂芳烃的跨环反应。该方法也成功地应用于一种螺双环胺的芳基化，这是一类在跨环CH活化反应中尚未研究的底物。目前，这种跨瓣环CH杂芳基化方法的广泛应用由于难以除去导向基团而受到阻碍。
• Photoinduced substitution reaction in halothiophenes. Quantum-mechanical and photochemical studies on nitro- and cyano-derivatives
  作者：L. Latterini、F. Elisei、G. G. Aloisi、M. D'Auria

  DOI：10.1039/b101993g

  日期：——

  2-Iodo-5-nitrothiophene, 2-iodo-5-cyanothiophene, 2-bromo-5-cyanothiophene and 4-iodo-nitrobenzene were studied by steady state and pulsed techniques and by semi-empirical quantum-mechanical calculations. The quantum yields for the direct and sensitized photoarylation of these haloaromatics following the photocleavage of the carbon–halogen bond were measured in benzene. The transient species (triplet

  通过稳态和脉冲技术以及半经验量子力学计算研究了2-碘-5-硝基噻吩、2-碘-5-氰基噻吩、2-溴-5-氰基噻吩和4-碘-硝基苯。在苯中测量了碳-卤素键光裂解后这些卤代芳烃的直接和敏化光芳基化的量子产率。通过苯和甲基环己烷中的纳秒激光闪光光解研究了由直接和敏化激光激发产生的瞬态物质（三重态和自由基）。瞬变的特征在于吸收光谱和衰减寿命。三重态还通过在低温下刚性基质中的磷光测量来表征。在甲基环己烷中测定了三重态的猝灭速率常数和产生单重态氧的量子产率。使用不同三重态能量的敏化剂获得的结果表明，上三重态参与了碳 - 卤素键的光裂解。
• Directed Functionalization of Cyano-Substituted Furans and Thiophenes with TMPMgCl·LiCl
  作者：Giuliano Clososki、Fernanda dos Santos、João Batista、Ricardo Vessecchi

  DOI：10.1055/s-0035-1560586

  日期：——

  A number of novel difunctionalized furans and thiophenes has been prepared by the reaction of the cyano-substituted substrates with TMPMgClLiCl followed by the reaction with electrophiles. The crucial metalation step takes place under mild conditions allowing the isolation of desired derivatives in reasonable to good yields.