1-(4-戊炔-1-基)-1H-吡咯 | 105763-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-(4-戊炔-1-基)-1H-吡咯
• 英文名称: 1-pent-4-ynyl-1H-pyrrole
• 英文别名: 1-(pent-4-yn-1-yl)-1H-pyrrole；N-(4-pentynyl)pyrrole；N-(pent-4-ynyl)pyrrole；1-Pent-4-ynylpyrrole
• CAS: 105763-05-1
• 化学式: C₉H₁₁N
• 分子量: 133.193
• InChiKey: JASZCLZEBUTDKV-UHFFFAOYSA-N

物化性质

• 沸点：
  160 °C(Press: 1 Torr)
• 密度：
  0.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(4-戊炔-1-基)-1H-吡咯 在 正丁基锂 、 氯化铂 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 10.5h， 生成 methyl 2-(6,7-dihydro-5H-indolizin-8-ylidene)acetate
  参考文献：
  名称：

  Pt(IV)-catalyzed cyclization of arene–alkyne substrates via C–H bond functionalization

  摘要：

  We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety. PtCl4 is compatible with both terminal and disubstituted alkynes, as well as with various functionalities on the arene ring, including methyl, methoxyl, hydroxyl, protected amine, and halide. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.05.003
• 作为产物：
  描述：

  吡咯 、 5-氯戊炔 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(4-戊炔-1-基)-1H-吡咯
  参考文献：
  名称：

  镍催化末端炔烃的不对称反选择性硼基烷基化

  摘要：

  炔三键向双键的选择性转化是构建取代烯烃的有效平台。尽管其时空调控已取得重大进展，但实现需要克服多方面选择性问题的多组分对映选择性反应仍然不常见。在这里，我们报告了通过镍催化对末端炔烃进行前所未有的不对称反立体选择性硼基碳官能化。利用廉价的手性二胺配体可以实现末端炔烃、二硼试剂和前手性烷基亲电子试剂的三组分交叉偶联，并具有高水平的区域选择性、立体选择性和对映选择性。该反应提供了一种有效的方案来获得带有α-立体中心的对映体富集的烯基酯，非常实用，并且具有广泛的范围和出色的官能团兼容性。此外，该方法的价值在后续的多种立体保留衍生化和复杂药物分子的立体选择性简明合成中也得到了凸显。

  DOI：

  10.1021/jacs.3c05969

文献信息

• Cp*Co(<scp>iii</scp>)-Catalyzed oxidative [5+2] annulation: regioselective synthesis of 2-aminobenzoxepines <i>via</i> C–H/O–H functionalization of 2-vinylphenols with ynamides
  作者：Xiang-Lei Han、Xu-Ge Liu、E Lin、Yunyun Chen、Zhuangzhong Chen、Honggen Wang、Qingjiang Li

  DOI：10.1039/c8cc06807k

  日期：——

  A Cp*Co(III)-catalyzed [5+2] C–H annulation reaction of 2-vinylphenols with ynamides was developed. The reaction led to the efficient synthesis of valuable 2-aminobenzoxepines in high regioselectivity. Mild reaction conditions, good functional group tolerance, and moderate to good yields were observed. The synthetic utility was demonstrated by a gram-scale synthesis and further transformations of the

  开发了Cp * Co（III）催化的2-乙烯基苯酚与乙酰胺的[5 + 2] CH环化反应。该反应导致在高区域选择性下有效合成有价值的2-氨基苯并x庚因。观察到温和的反应条件，良好的官能团耐受性和中等至良好的产率。通过克规模的合成和产物的进一步转化证明了合成的效用。进行了初步的机理研究，并提出了可能的催化循环。
• Pyrrolyl-, 2-(2-thienyl)pyrrolyl- and 2,5-bis(2-thienyl)pyrrolyl-nucleosides: synthesis, molecular and electronic structure, and redox behaviour of C5-thymidine derivatives
  作者：Miguel A. Galindo、Jennifer Hannant、Ross W. Harrington、William Clegg、Benjamin R. Horrocks、Andrew R. Pike、Andrew Houlton

  DOI：10.1039/c0ob00466a

  日期：——

  A series of modified nucleosides based on thymidine have been prepared by Pd-catalysed cross-coupling between N-alkyl-alkynyl functionalised pyrrolyl- (py), 2-(2-thienyl)pyrrolyl- (tp) or 2,5-bis(2-thienyl)pyrrolyl (tpt) groups with 5-iodo-2′-deoxyuridine. The length of the alkyl chain linking the nucleoside and pyrrolyl-containing unit, N(CH2)nCC-nucleoside (where n = 1–3) was also varied. The compounds have been characterised by 1H NMR, ES-MS, UV–vis, cyclic voltammetry (CV) and, in some cases, single-crystal X-ray diffraction. Cyclic voltammetry studies demonstrated that all the py-, tp- and tpt-alkynyl derivatives 1–7 can be electrochemically polymerised to form conductive materials. It was found that increasing the N-alkyl chain length in these cases resulted in only minor changes in the oxidation potential. The same behaviour was observed for the tp- and tpt-modified nucleosides 9–12; however, the py-derivative, 8, produced a poorly conducting material. DFT calculations on the one-electron oxidised cation of the modified nucleosides bearing tp or tpt showed that spin density is located on the pyrrolyl and thienyl units in all cases and that the coplanarity of adjacent rings increases upon oxidation. In contrast, in the corresponding pyrrolyl cases the spin density is distributed over the whole molecule, suggesting that polymerisation does not occur solely at the pyrrolyl-Cα position and the conjugation is interrupted.

  通过钯催化交叉偶联，在N-烷基-炔基官能化的吡咯基（py）、2-(2-噻吩基)吡咯基（tp）或2,5-双(2-噻吩基)吡咯基（tpt）基团与5-碘-2′-脱氧尿苷之间，制备了一系列基于胸苷的修饰核苷。连接核苷和含吡咯基单元的烷基链长度（N(CH2)nCC-核苷，其中n = 1-3）也各不相同。通过1H NMR、ES-MS、UV-vis、循环伏安法（CV）以及某些情况下的单晶X射线衍射，对化合物进行了表征。循环伏安法研究表明，所有py、tp和tpt-炔基衍生物1-7都可以电化学聚合形成导电材料。研究发现，在这种情况下，增加N-烷基链长度只会导致氧化电位发生微小变化。tp和tpt修饰核苷9-12也表现出相同的行为；然而，py衍生物8产生的导电材料效果不佳。对带有tp或tpt修饰核苷的单电子氧化阳离子进行DFT计算表明，在所有情况下，自旋密度都位于吡咯基和
• Cobalt-Mediated [2+2+2] Cycloaddition of Alkynyl Boronates to Indole and Pyrrole Double Bonds
  作者：K. Vollhardt、Sabine Amslinger、Corinne Aubert、Vincent Gandon、Max Malacria、Elisa Paredes

  DOI：10.1055/s-2008-1077950

  日期：——

  The complex [CpCo(C2H4)2] facilitates the [2+2+2] cycloaddition of borylalkynes to N-(4-pentynoyl)indole and -pyrrole to furnish heterocyclofused borylcyclohexadienes regioselectively.

  复合物 [CpCo(C2H4)2] 可促进硼烷与 N-(4-戊炔酰基)吲哚和吡咯的 [2+2+2] 环加成反应，从而有选择性地生成杂环融合的硼环己二烯。
• SHEPPARD G. S.; VOLLHARDT K. P. C., J. ORG. CHEM., 51,(1986) N 26, 5496-5498
  作者：SHEPPARD G. S.、 VOLLHARDT K. P. C.

  DOI：——

  日期：——
• CN116354995
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