2-(5-phenyl-4-pentynyl)furan | 934667-85-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(5-phenyl-4-pentynyl)furan
• 英文别名: 2-(5-phenylpent-4-yn-1-yl)furan；2-(5-phenylpent-4-ynyl)furan；2-(5-Phenylpent-4-ynyl)furan
• CAS: 934667-85-3
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: UOGFZZXGENFEFX-UHFFFAOYSA-N

物化性质

• 沸点：
  330.0±25.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(5-phenyl-4-pentynyl)furan 在 mercury(II) diacetate scandium tris(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 17.0h， 以90%的产率得到(Z)-4-phenyl-7,8-dihydro-6H-cyclohepta[b]furan
  参考文献：
  名称：

  Hg(OAc)₂·0.1Sc(OTf)₃-Catalyzed Cycloisomerization of 2-(4-Pentynyl)furan

  摘要：

  Although the Hg(OTf)(2)center dot 3TMU-catalyzed Friedel-Crafts-type reaction of 3-(4-pentynyl)furan afforded the exo cyclization product, the reaction of 2-(4-pentynyl)furan furnished a very low yield. We found a 10:1 mixed reagent of Hg(OAc)(2) and Sc(OTf)(3) showed remarkable catalytic activity for the latter transformation. The actual reacting species is presumed to be Hg(OAc)(OTf), which is efficiently generated in situ by mixing the two reagents.

  DOI：

  10.1021/ol070335m
• 作为产物：
  描述：

  2-呋喃丙醇 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.84h， 生成 2-(5-phenyl-4-pentynyl)furan
  参考文献：
  名称：

  Hg(OAc)₂·0.1Sc(OTf)₃-Catalyzed Cycloisomerization of 2-(4-Pentynyl)furan

  摘要：

  Although the Hg(OTf)(2)center dot 3TMU-catalyzed Friedel-Crafts-type reaction of 3-(4-pentynyl)furan afforded the exo cyclization product, the reaction of 2-(4-pentynyl)furan furnished a very low yield. We found a 10:1 mixed reagent of Hg(OAc)(2) and Sc(OTf)(3) showed remarkable catalytic activity for the latter transformation. The actual reacting species is presumed to be Hg(OAc)(OTf), which is efficiently generated in situ by mixing the two reagents.

  DOI：

  10.1021/ol070335m

文献信息

• Switch in Selectivity for Formal Hydroalkylation of 1,3‐Dienes and Enynes with Simple Hydrazones
  作者：Leiyang Lv、Lin Yu、Zihang Qiu、Chao‐Jun Li

  DOI：10.1002/anie.201915875

  日期：2020.4.16

  anti-Markovnikov addition is obtained by changing to a ruthenium catalyst, thus providing direct and efficient access to homoallylic products exclusively. Isotopic substitution experiments indicate that no reversible hydro-metallation across the metal-π-allyl system occurred under ruthenium catalysis. Moreover, this protocol is applicable to the regiospecific hydroalkylation of the distal C=C bond of 1,3-enynes

  控制反应选择性是化学家的永恒追求。区域选择性催化利用和/或克服了固有的空间和电子偏向性，可以从相同的起始原料中提供多种区域富集的产物，是发散合成的强大工具。最近，据报道当使用镍催化剂时，用简单的azo酮进行的1，3-二烯的1，2-马氏化学加氢烷基化反应生成支链烯丙基化合物。作为工作的一部分，此处显示的是通过更换钌催化剂获得了马尔科夫尼科夫向反马尔科夫尼科夫添加的完全转换，从而提供了直接有效地专门获得均聚物的途径。同位素取代实验表明，在钌催化下，整个金属-π-烯丙基系统均未发生可逆的加氢金属化反应。此外，
• Ni-Catalyzed Sonogashira Coupling of Nonactivated Alkyl Halides: Orthogonal Functionalization of Alkyl Iodides, Bromides, and Chlorides
  作者：Oleg Vechorkin、Delphine Barmaz、Valérie Proust、Xile Hu

  DOI：10.1021/ja906040t

  日期：2009.9.2

  Ni-catalyzed Sonogashira coupling of nonactivated, beta-H-containing alkyl halides, including chlorides, is reported. The coupling is tolerant to a wide range of functional groups, including ether, ester, amide, nitrile, keto, heterocycle, acetal, and aryl halide, in both coupling partners. The coupling can be selective for a specific C-X bond (X = I, Br, Cl) and allows for orthogonal functionalization

  据报道，Ni 催化的 Sonogashira 偶联未活化的、含 β-H 的烷基卤化物，包括氯化物。偶联可以耐受多种官能团，包括醚、酯、酰胺、腈、酮、杂环、乙缩醛和芳基卤化物，在两种偶联伙伴中。偶联可以对特定的 CX 键 (X = I, Br, Cl) 具有选择性，并允许具有多个反应位点的卤代烷正交官能化。
• Hg(OAc)₂·0.1Sc(OTf)₃-Catalyzed Cycloisomerization of 2-(4-Pentynyl)furan
  作者：Hirofumi Yamamoto、Ikuo Sasaki、Hiroshi Imagawa、Mugio Nishizawa

  DOI：10.1021/ol070335m

  日期：2007.3.1

  Although the Hg(OTf)(2)center dot 3TMU-catalyzed Friedel-Crafts-type reaction of 3-(4-pentynyl)furan afforded the exo cyclization product, the reaction of 2-(4-pentynyl)furan furnished a very low yield. We found a 10:1 mixed reagent of Hg(OAc)(2) and Sc(OTf)(3) showed remarkable catalytic activity for the latter transformation. The actual reacting species is presumed to be Hg(OAc)(OTf), which is efficiently generated in situ by mixing the two reagents.