2-vinyl-4-benzoyl-5-methyl-2,3-dihydrofuran | 113949-31-8

• 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-vinyl-4-benzoyl-5-methyl-2,3-dihydrofuran
• 英文别名: (2-methyl-5-vinyl-4,5-dihydrofuran-3-yl)(phenyl)methanone；(2-Ethenyl-5-methyl-2,3-dihydrofuran-4-yl)-phenylmethanone
• CAS: 113949-31-8
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: ZOTVYYLNNLBWBG-UHFFFAOYSA-N

物化性质

• 沸点：
  311.9±42.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  1-(trimethylsiloxy)-1-phenyl-1-buten-3-one 在 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 反应 1.0h， 生成 2-vinyl-4-benzoyl-5-methyl-2,3-dihydrofuran
  参考文献：
  名称：

  Novel synthesis of dihydrofurans from the addition of enolate dianion derivatives to (.eta.4-diene)Co(CO)3BF4

  摘要：

  DOI：

  10.1021/jo00244a053

文献信息

• Organocatalytic Cloke–Wilson Rearrangement: DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans
  作者：Jingfang Zhang、Yuhai Tang、Wen Wei、Yong Wu、Yang Li、Junjie Zhang、Yuansuo Zheng、Silong Xu

  DOI：10.1021/acs.orglett.7b00805

  日期：2017.6.16

  An organocatalytic Cloke–Wilson rearrangement of cyclopropyl ketones to 2,3-dihydrofurans is exploited utilizing the homoconjugate addition process. With 1,4-diazabicyclo[2.2.2]octane as the catalyst, the rearrangement in DMSO at 120 °C proceeded in generally high yields, exclusive regioselectivity, and a broad substrate scope. An examination of the mechanism including stereochemical analysis and intermediate

  利用均轭共轭加成工艺开发了环丙基酮对2，3-二氢呋喃的有机催化Cloke-Wilson重排。以1,4-二氮杂双环[2.2.2]辛烷为催化剂，在DMSO中于120°C进行的重排通常以高收率，唯一的区域选择性和较宽的底物范围进行。该机构包括立体化学分析和中间隔离支撑一个S的检查Ñ机制的1型环开口。
• Organocatalytic Cloke–Wilson Rearrangement: Carbocation-Initiated Tandem Ring Opening/Cyclization of Cyclopropanes under Neutral Conditions
  作者：Guisheng Zhang、Liming Chen、Zhaokang Hu、Zhiguo Zhang、Jingjing Bi、Mengjuan Li、Xingjie Zhang

  DOI：10.1021/acs.joc.2c02415

  日期：2023.1.20

  We report a metal-, acid-, and base-free 2-(bromomethyl)naphthalene (2-BMN)-promoted organocatalytic Cloke–Wilson rearrangement of chain doubly activated cyclopropanes for the construction of 2,3-dihydrofurans via a carbocation-initiated tandem intramolecular ring-opening/recyclization process. The strategy is especially suitable for the construction of furan units in complex molecules, providing a

  我们报道了一种不含金属、酸和碱的 2-(溴甲基) 萘 (2-BMN) 促进的有机催化 Cloke-Wilson 重排链双活化环丙烷，用于通过碳阳离子引发的 2,3-二氢呋喃的构建串联分子内开环/再循环过程。该策略特别适用于复杂分子中呋喃单元的构建，为传统基于金属的方案合成的含二氢呋喃药物中的重金属残留问题提供了解决方案。因此，它在合成和药物化学中具有潜在的意义。
• Barinelli, Lucio S.; Li, Zhong; Nicholas, Kenneth M., Organometallics, 1989, vol. 8, # 10, p. 2474 - 2476
  作者：Barinelli, Lucio S.、Li, Zhong、Nicholas, Kenneth M.

  DOI：——

  日期：——
• Cyclodehydration of cis–2-butene-1,4-diol with active methylene compounds catalyzed by a diphosphinidenecyclobutene-coordinated palladium complex
  作者：Hiromi Murakami、Yukio Matsui、Fumiyuki Ozawa、Masaaki Yoshifuji

  DOI：10.1016/j.jorganchem.2006.03.011

  日期：2006.7

  (pi-Allyl)palladium triflate coordinated with 1,2-bis(4-methoxyphenyl)-3,4-bis(2,4,6-tri-t-butylphenylphosphinidene)cyclobutene (DPCB-OMe), [Pd(eta(3)-C3H5)(DPCB-OMe)]OTf, efficiently catalyzes cycl odehydration of cis-2-butene-1,4-diol with active methylene compounds such as acetylacetone and ethyl acetoacetate in toluene in the presence of pyridine. The reactions can be performed in air, giving 2-vinyl-2,3-dihydrofurans in good to high yields. (c) 2006 Elsevier B.V. All rights reserved.
• BARINELLI, LUCIO S.;NICHOLAS, KENNETH M., J. ORG. CHEM., 53,(1988) N 9, 2114-2117
  作者：BARINELLI, LUCIO S.、NICHOLAS, KENNETH M.

  DOI：——

  日期：——