5-(4-methoxyphenyl)-2,3-dimethylfuran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-methoxyphenyl)-2,3-dimethylfuran
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: WIRYVJAUUXFIIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 作用下， 反应 10.0h， 以83%的产率得到5-(4-methoxyphenyl)-2,3-dimethylfuran
  参考文献：
  名称：

  铱（I）催化的（Z）-2-En-4-yn-1-ols与活化的炔烃的偶联反应：合成7-恶臭降冰片二烯的新途径

  摘要：

  利用铱（I）二聚体[{Ir（μ-Cl）（COD）} 2 ]表现出的能力来促进（Z）-烯醇转化为呋喃的环异构化，已经有史无前例的合成方法合成7-氧杂硼烷二烯通过在活化炔烃的存在下进行催化反应而开发的。该方法在无溶剂条件下进行，以高收率和完全的原子经济性提供了双环烯烃。

  DOI：

  10.1002/adsc.201000408

文献信息

• 酮与alpha氯代酮一步反应合成呋喃类化合物的方法
  申请人：重庆医科大学

  公开号：CN113861137B

  公开（公告）日：2023-08-15

  本发明提供一种以alpha‑氯代酮和甲基酮或环酮为原料，在略微过量的钛酸四异丙酯作用下，无溶剂条件下一步反应制备多取代呋喃化合物的方法。即在惰性气体保护下，将甲基酮或环酮、α‑氯代酮和对甲苯磺酸的反应混合物搅拌加热升温后，加入钛酸四异丙酯进行反应，反应结束后再将所得反应混合物进行分离提纯，得到多取代呋喃化合物。本发明所述的合成方法，原料易得，成本低廉，操作简单易控，无需溶剂，有良好的底物普适性和官能团兼容性，适宜于工业化大生产。
• Titanium-Mediated Domino Cross-Coupling/Cyclodehydration and Aldol-Addition/Cyclocondensation: Concise and Regioselective Synthesis of Polysubstituted and Fused Furans
  作者：Lu Ren、Juan Luo、Linbo Tan、Qiang Tang

  DOI：10.1021/acs.joc.1c02894

  日期：2022.3.4

  Titanium enolates, in situ-generated from readily available ketones and titanium tetraisopropoxide, undergo domino cross-coupling/cyclodehydration or domino Aldol-addition/cyclocondensation with α-chloroketones to provide synthetically valuable furan derivatives. The domino process tolerates a variety of cyclic and acyclic ketones and chloroketones, producing polysubstituted furans and bi-, tri-, and

  由容易获得的酮和四异丙醇钛原位生成的钛烯醇化物与α-氯酮进行多米诺交叉偶联/环脱水或多米诺醛醇加成/环缩合，以提供具有合成价值的呋喃衍生物。多米诺工艺耐受多种环状和非环状酮和氯酮，产生多取代呋喃和双环、三环和四环稠合呋喃。
• Imine Compound
  申请人：Saito Shiuji

  公开号：US20080312435A1

  公开（公告）日：2008-12-18

  An imine compound represented by the formula: wherein A represents a heterocyclic group; R 1 , R 2 , an R 3 each represent a hydrogen atom, a halogen atom, a C 1-10 alkyl group optionally substituted with an aryl group(s) substituted with a halogen atom(s), a C 3-10 cycloalkyl group, a C 1-6 haloalkyl group, a C 1-10 alkoxy group, etc.; R 4 represents an optionally substituted C 1-10 alkyl, C 2-6 alkenyl, or aryl group; R 5 represents a hydrogen atom, a C 1-10 alkoxy group, a C 1-6 haloalkyl group, an optionally substituted C 1-10 alkyl or C 2-6 alkenyl group, an optionally substituted aryl or heterocyclic group, etc.; W represents —CO—, —CO—CO—, —CO—NH—, —CS—NH—, or —SO 2 —, or a cannabinoid-receptor agonist comprising said imine compound as an active ingredient. The imine compound of the present invention has a cannabinoid-receptor agonist effect, and is useful as a therapeutic or prophylactic drug for pains and autoimmune diseases.

  一种以以下式表示的亚胺化合物：其中A代表杂环基团；R1、R2和R3分别表示氢原子、卤素原子、C1-10烷基，该烷基可选地取代有芳基，所述芳基取代有卤素原子，C3-10环烷基，C1-6卤代烷基，C1-10烷氧基等；R4表示可选地取代的C1-10烷基，C2-6烯基或芳基；R5表示氢原子，C1-10烷氧基，C1-6卤代烷基，可选地取代的C1-10烷基或C2-6烯基，可选地取代的芳基或杂环基团等；W表示—CO—，—CO—CO—，—CO—NH—，—CS—NH—或—SO2—，或以该亚胺化合物为活性成分的大麻素受体激动剂。本发明的亚胺化合物具有大麻素受体激动剂作用，可用作治疗或预防疼痛和自身免疫性疾病的药物。
• Ring-opening of tertiary cyclopropanols derived from β-diketones
  作者：Le-Zhen Li、Bin Xiao、Qing-Xiang Guo、Song Xue

  DOI：10.1016/j.tet.2006.05.064

  日期：2006.8

  The ring-opening reaction of 1,2-di substituted cyclopropanols, prepared from beta-diketones, mediated by Cu(NO3)(2), p-TsOH, and NaOH is reported. The Cu(II)-mediated ring-opening of cyclopropanols gave alpha-methylene-gamma-diketones in good yields. The reaction took place at the less substituted carbon of the cyclopropanols, involving mild conditions and a simple procedure. The reaction induced by p-TsOH in CH2O2 afforded alpha-methyl-gamma-diketones as the major product with minor amounts of 8-diketones. The 2,3,5-tri substituted furans were obtained in high yields when the ring-opening reaction was mediated by p-TsOH in methanol under reflux conditions. In the presence of sodium hydroxide the reaction proceeded smoothly in preference to the formation of beta-diketones, particularly for substrates with an aromatic group on the cyclopropane. (c) 2006 Elsevier Ltd. All rights reserved.
• Iridium(I)-Catalyzed Coupling of (Z)-2-En-4-yn-1-ols with Activated Alkynes: A New Synthetic Route to 7-Oxanorbornadienes
  作者：Alba E. Díaz-Álvarez、Pascale Crochet、Victorio Cadierno

  DOI：10.1002/adsc.201000408

  日期：2010.10.4

  Taking advantage of the ability shown by the iridium(I) dimer [Ir(μ-Cl)(COD)}2] to promote the cycloisomerization of (Z)-enynols into furans, an unprecedented synthetic route to 7-oxanorbornadienes has been developed just by performing the catalytic reactions in the presence of activated alkynes. The process, which proceeds under solvent-free conditions, furnishes the bicyclic alkenes in good yields

  利用铱（I）二聚体[Ir（μ-Cl）（COD）} 2 ]表现出的能力来促进（Z）-烯醇转化为呋喃的环异构化，已经有史无前例的合成方法合成7-氧杂硼烷二烯通过在活化炔烃的存在下进行催化反应而开发的。该方法在无溶剂条件下进行，以高收率和完全的原子经济性提供了双环烯烃。