5-(2-furyl)-1-pentyne | 142458-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 5-(2-furyl)-1-pentyne
• 英文别名: 2-(4-pentynyl)furan；2-(pent-4-yn-1-yl)furan；2-Pent-4-ynylfuran
• CAS: 142458-86-4
• 化学式: C₉H₁₀O
• 分子量: 134.178
• InChiKey: FOGSBIIOPRNRBN-UHFFFAOYSA-N

物化性质

• 沸点：
  180.0±23.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(2-furyl)-1-pentyne 在 Schwartz's reagent 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 10.67h， 生成 (1S,5S,11R,12R)-15-oxatetracyclo[10.2.1.01,5.07,11]pentadeca-6,13-dien-10-one
  参考文献：
  名称：

  通过光诱导的环异构化反应 以模块化方式访问功能化的5–8–5稠环系统†

  摘要：

  5–8–5碳环系统构成了30多种不同的天然产物的核心。该家族的几个成员因其在细胞培养中的多种活性而受到关注。在这些情况下，生物学功能是由保守的5-8-5核周围取代基的排列介导的。尽管这种特权子结构可能在药物化学中得到应用，但其组装的模块化策略仍未得到开发。在本文中，我们描述了直接形成5-8-5骨架的环异构化反应。这种策略独特地允许通过四个步骤来访问克量的这种有价值的支架。

  DOI：

  10.1039/c8sc00999f
• 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 5-(2-furyl)-1-pentyne
  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

• Fusicoccane Derivatives and Methods
  申请人：Florida State University Research Foundation, Inc.

  公开号：US20180312518A1

  公开（公告）日：2018-11-01

  Provided are fusicoccane derivatives and methods of making fusicoccane derivatives. The methods may include contacting a tethered chromophore with light to initiate a photoinduced pericyclic reaction cascade to form a 5-8-5 carbotricycle. The 5-8-5 carbotricycle may be further functionalized.

  提供的是fusicoccane衍生物以及制备fusicoccane衍生物的方法。这些方法可能包括用光照射束缚色素以启动光诱导的周环反应级联，形成5-8-5碳三环。5-8-5碳三环可以进一步官能化。
• Stereospecific and Regioselective Synthesis of <i>E</i>-Allylic Alcohols through Reductive Cross Coupling of Terminal Alkynes
  作者：Austin B. Shaff、Langxuan Yang、Mitchell T. Lee、Gojko Lalic

  DOI：10.1021/jacs.3c06963

  日期：——

  convergent method for the synthesis of allylic alcohols that involves a reductive coupling of terminal alkynes with α-chloro boronic esters. The new method affords allylic alcohols with excellent regioselectivity (anti-Markovnikov) and an E/Z ratio greater than 200:1. The reaction can be performed in the presence of a wide range of functional groups and has a substrate scope that complements the stoichiometric

  我们开发了一种合成烯丙醇的收敛方法，涉及末端炔烃与 α-氯硼酸酯的还原偶联。新方法提供了具有优异区域选择性（抗马尔可夫尼科夫）和大于 200:1 的 E/Z 比的烯丙醇。该反应可以在多种官能团存在下进行，并且底物范围可补充使用烯基锂和格氏试剂进行的 α-氯硼酸酯的化学计量烯基化。该转化是立体定向的，可以稳健且高度选择性地合成手性烯丙醇。我们的研究支持涉及炔烃氢化以及烯基铜中间体与α-氯硼酸酯交叉偶联的机制。实验证据排除了交叉偶联步骤的根本机制，并且与硼酸盐中间体的形成和1,2-金属化物转变一致。
• Fusicoccane derivatives and methods
  申请人：Florida State University Research Foundation, Inc.

  公开号：US10253038B2

  公开（公告）日：2019-04-09

  Provided are fusicoccane derivatives and methods of making fusicoccane derivatives. The methods may include contacting a tethered chromophore with light to initiate a photoinduced pericyclic reaction cascade to form a 5-8-5 carbotricycle. The 5-8-5 carbotricycle may be further functionalized.

  本发明提供了番荔枝烷衍生物和制造番荔枝烷衍生物的方法。这些方法可包括将系链发色团与光接触，以启动光诱导的周环级联反应，形成 5-8-5 碳三环。5-8-5 碳三环可进一步官能化。
• Rhodium carbenoid mediated cyclizations of o-alkynyl-substituted .alpha.-diazoacetophenones
  作者：Albert Padwa、Keith E. Krumpe、Jamal M. Kassir

  DOI：10.1021/jo00044a032

  日期：1992.8

  o-Alkynyl-substituted alpha-diazoacetophenones undergo facile cyclization to indenone derivatives upon treatment with catalytic quantities of Rh(II) carboxylates. A variety of structural influences were encountered by varying the nature of the substituent group attached to the alkyne carbon atom. The cyclization reaction involves addition of a rhodium stabilized carbenoid onto the acetylenic pi-bond to generate a vinyl carbenoid. The vinyl carbenoid was found to undergo both CH and CC migration as well as delta-CH insertion into the alkyl backbone. Different catalysts were shown to result in significant variation in the product ratios for these reactions. Treatment of o-(5-(allyloxy)-1-pentynyl)-alpha-diazoacetophenone with rhodium(II) mandelate afforded 2-(2-propen-1-yl)-2-(1-oxo-1H-indenyl)-2,3,4,5-tetrahydrofuran in high yield. The formation of this compound involves initial formation of a vinyl carbenoid which reacts with the neighboring oxygen atom to give an oxonium ylide which subsequently undergoes a 2,3-sigmatropic rearrangement. When 2-ethynyl-alpha-diazoacetophenone is used, only products derived from 6-endo closure are observed. Substituted o-alkynyl alpha-diazoacetophenones give products derived from 5-exo cyclization. The mode of ring closure is controlled by both steric and electronic factors.
• 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.