2,6,6-trimethyl-2-(prop-1-en-2-yl)-2,3,6,7-tetrahydrobenzofuran-4(5H)one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2,6,6-trimethyl-2-(prop-1-en-2-yl)-2,3,6,7-tetrahydrobenzofuran-4(5H)one
• 英文别名: 6,6-dimethyl-2-(prop-1-en-2-yl)-2,3,6,7-tetrahydrobenzofuran-4(5H)-one；2-isopropenyl-2,6,6-trimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one；2,6,6-trimethyl-2-isopropenyl-2,3,4,5,6,7-hexahydrobenzofuran-4-one；2,6,6-trimethyl-2-prop-1-en-2-yl-5,7-dihydro-3H-1-benzofuran-4-one
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: AOHJKTFFGZEHNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-重氮基-5,5-二甲基-1,3-环己二酮 、 2,3-二甲基-1,3-丁二烯 在 tris(triphenylphosphine)ruthenium(II) chloride 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以87%的产率得到2,6,6-trimethyl-2-(prop-1-en-2-yl)-2,3,6,7-tetrahydrobenzofuran-4(5H)one
  参考文献：
  名称：

  钌（II）催化的[3 + 2]环或无环重氮二羰基化合物与烯烃的环加成反应，高效一锅合成多取代的二氢呋喃

  摘要：

  AbstractRuthenium(II)‐phosphine complexes‐catalyzed [3+2] cycloadditions were conducted to synthesize a variety of dihydrofurans by reactions of cyclic or acyclic diazodicarbonyl compounds with olefins. This method represents a direct and efficient one‐pot synthesis for multi‐substituted dihydrofurans under mild reaction conditions with an excellent regioselectivity. Furthermore, to reduce reaction times and increase yields of dihydrofurans, microwave‐assisted tris(triphenylphosphine)ruthenium(II) chloride/ 1‐butyl‐3‐methylimidazolium tetrafluoroborate {Ru(PPh3)3Cl2/[Bmim]BF4}‐catalyzed reactions were also developed. The synthesized dihydrofurans can be readily converted into biologically interesting tetrahydroindoles.magnified image

  DOI：

  10.1002/adsc.201300245

文献信息

• Rhodium(II)-Catalyzed Reaction of Iodonium Ylides with Conjugated Compounds: Efficient Synthesis of Dihydrofurans, Oxazoles, and Dihydrooxepines
  作者：Yong Lee、Sang Yoon、Youngwan Seo、Bong Kim

  DOI：10.1055/s-2004-831257

  日期：——

  The rhodium(II)-catalyzed reaction of iodonium ylides with a variety of conjugated compounds has been examined. With α,β-unsaturated esters and α,β-unsaturated ketones, dihydrofurans were produced in moderate yields. Reactions with acrylonitriles yield oxazoles and dihydrofurans in moderate yields, whereas reactions with 1,3-butadienes result in dihydrofurans and dihydrooxepines in good yields, respectively

  已经检查了碘鎓叶立德与各种共轭化合物的铑 (II) 催化反应。使用 α,β-不饱和酯和 α,β-不饱和酮，以中等收率生产二氢呋喃。与丙烯腈反应以中等收率产生恶唑和二氢呋喃，而与 1,3-丁二烯反应分别以良好收率产生二氢呋喃和二氢氧杂环庚烷。形成这些产物的机理途径已根据环丙烷中间体或 1,3-偶极环加成机理进行了描述。
• Efficient Synthesis of Five- and Seven-Membered-Ring Heterocycles by Rhodium(II)-Catalyzed [3+2] and [3+4] Cycloaddition of Diazodicarbonyl Compounds with Conjugated Dienes
  作者：Yong Rok Lee、Jae Cheol Hwang

  DOI：10.1002/ejoc.200400452

  日期：2005.4

  Rhodium(II)-catalyzed reactions of diazodicarbonyl compounds with a variety of conjugated dienes have been examined. These reactions provide a simple and rapid route to dihydrofurans and dihydrooxepines with a variety of substituents on the ring. The formation of these products is interpreted in terms of a stepwise mechanism. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  已经研究了铑 (II) 催化的重氮二羰基化合物与各种共轭二烯的反应。这些反应为环上具有多种取代基的二氢呋喃和二氢氧杂环庚烷提供了一种简单而快速的途径。这些产物的形成被解释为逐步机制。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Cycloaddition Reactions of Iodonium Ylides of Cyclic <i>β</i>-Diketones with 1,3-Dienes: Evidence for a Stepwise Mechanism
  作者：Ioannis Alexiou、Efstathios P. Gogonas、Lazaros P. Hadjiarapoglou

  DOI：10.1055/s-1999-2970

  日期：1999.12

  The irradiation of a cyclic β-dicarbonyl iodonium ylide with 1,3-diene in acetonitrile gives substituted dihydrofurans in moderate to high yields, presumably via a stepwise mechanism.

  在乙腈中用 1,3- 二烯辐照环状 δ-二羰基碘化铵，可以得到中到高产率的取代二氢呋喃，这可能是通过一种逐步推进的机制实现的。
• Ceric Ammonium Nitrate (CAN)-Mediated Oxidative Cycloaddition of 1,3-Dicarbonyls to Conjugated Compounds. Efficient Synthesis of Dihydrofurans, Dihydrofurocoumarins, Dihydrofuroquinolinones, Dihydrofurophenalenones, and Furonaphthoquinone Natural Products
  作者：Yong Rok Lee、Byung So Kim、Dae Hwan Kim

  DOI：10.1016/s0040-4020(00)00839-5

  日期：2000.11

  Ceric ammonium nitrate-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds afforded substituted dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, and dihydrofurophenalenones in moderate yields. This new synthetic method has been applied to the synthesis of furonaphthoquinone natural products. (C) 2000 Elsevier Science Ltd. All rights reserved.
• KR2016/20022
  申请人：——

  公开号：——

  公开（公告）日：——