3-(5-ethyl-2-furyl)-1-propanol | 174606-87-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(5-ethyl-2-furyl)-1-propanol
• 英文别名: 3-(5-ethylfuran-2-yl)propan-1-ol；3-(5-ethyl-2-furanyl)propan-1-ol；5-Ethyl-2-(3-hydroxypropyl)furan
• CAS: 174606-87-2
• 化学式: C₉H₁₄O₂
• mdl: MFCD09927290
• 分子量: 154.209
• InChiKey: ANHPOLACYHKELJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(5-ethyl-2-furyl)-1-propanol 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 16.5h， 生成
  参考文献：
  名称：

  Acid-Promoted Cyclization Reactions of Tetrahydroindolinones. Model Studies for Possible Application in a Synthesis of Selaginoidine

  摘要：

  [GRAPHIC]The synthesis of various substituted bicyclic lactams by an acid-induced Pictet-Spengler reaction of tetrahydroindolinones bearing tethered heteroaromatic rings is presented. The outcome of the cyclization depends on the position of the furan tether, tether length, nature of the tethered heteroaromatic ring, and the substituent group present on the 5-position of the tethered heteroaryl group. A one-pot procedure was developed to efficiently prepare tetrahydroindolinones containing tethered furan rings. In a typical example, the reaction of furanyl azide 26 with n-Bu3P delivered iminophosphorane 27, which was allowed to react with a 1-alkyl-(2-oxocyclohexyl)acetic acid to provide the desired furanyl-substituted tetrahydroindolinone system 29. Treatment of 29 with trifluoroacetic acid afforded the tetracyclic lactam skeleton 30 found in the alkaloid (+/-)-selaginoidine.

  DOI：

  10.1021/jo0619783
• 作为产物：
  描述：

  2-呋喃丙醇 在 正丁基锂 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 生成 3-(5-ethyl-2-furyl)-1-propanol
  参考文献：
  名称：

  呋喃合成7。（+/-）-perhydrohistrionicotoxin的正式全合成

  摘要：

  报道了（+/-）-过氢组蛋白毒素的正式全合成。该序列利用区域特异性-酰基酰亚胺离子引发的呋喃终止的环化作用来构建所需的氮杂螺[5.5]十一烷环系统。

  DOI：

  10.1016/s0040-4039(00)95450-9

文献信息

• 2,5-Oxyarylation of Furans: Synthesis of Spiroacetals via Palladium-Catalyzed Aerobic Oxidative Coupling of Boronic Acids with α-Hydroxyalkylfurans
  作者：Jiuyi Li、Hui Peng、Furong Wang、Xiujun Wang、Huanfeng Jiang、Biaolin Yin

  DOI：10.1021/acs.orglett.6b01472

  日期：2016.7.1

  A protocol for the 2,5-oxyarylation of furan rings via Pd-catalyzed aerobic oxidative coupling of boronic acids with α-hydroxyalkylfurans is reported. This protocol provides rapid, green access to diverse biologically interesting and synthetically useful unsaturated spiroacetals from sustainable furan derivatives.

  报道了通过硼酸与α-羟烷基呋喃的Pd催化的好氧氧化偶合使呋喃环的2,5-氧合的方案。该方案可快速，绿色地从可持续的呋喃衍生物中获得各种生物学上有趣且可合成有用的不饱和螺缩醛。
• Strain-Activated Diels–Alder Trapping of 1,2-Cyclohexadienes: Intramolecular Capture by Pendent Furans
  作者：Verner A. Lofstrand、Kyle C. McIntosh、Yaseen A. Almehmadi、F. G. West

  DOI：10.1021/acs.orglett.9b02085

  日期：2019.8.16

  Intramolecular [4 + 2] cycloaddition reactions of substituted 1,2-cyclohexadienes with pendent furans enables the synthesis of complex tetracyclic scaffolds in a single step under mild conditions. All Diels–Alder cycloadducts were obtained as single diastereomers, assigned as the endo isomer. Substrates were easily assembled via Stork–Danheiser alkylation of 3-ethoxy-2-bromocyclohex-2-enone to accommodate

  取代的1,2-环己二烯与侧基呋喃的分子内[4 + 2]环加成反应可在温和条件下一步合成复杂的四环骨架。所有Diels–Alder环加合物均作为单一非对映异构体获得，被指定为内聚异构体。可以通过3-乙氧基-2-溴环己基-2-烯酮的Stork–Danheiser烷基化轻松组装基板，以容纳一系列的系链和呋喃捕集阱。烯醇乙酸酯部分的切割导致室温的狄尔斯-阿尔德环还原为拴系的呋喃基环己烯酮。
• An Aza-Wittig/π-Furan Cyclization Approach Toward the Homoerythrina Alkaloid (±)-Selaginoidine
  作者：Michael P. Cassidy、Ayse Daut Özdemir、Albert Padwa

  DOI：10.1021/ol0501323

  日期：2005.3.1

  react with 1-methyl-(2-oxocyclohexyl)acetic acid to give the desired hexahydroindolinone ring system. Further treatment with trifluoroacetic acid afforded the tetracyclic lactam skeleton found in the alkaloid (+/-)-selaginoidine.

  [反应：见正文]开发了一种一锅法，以有效地制备含有束缚的呋喃环的六氢吲哚满酮。呋喃基叠氮化物与Bu 3 P的反应得到亚氨基磷烷，使其与1-甲基-（2-氧代环己基）乙酸反应，得到所需的六氢吲哚酮环系统。用三氟乙酸进一步处理，得到在生物碱（+/-）-硒代嘧啶中发现的四环内酰胺骨架。
• Therapeutic phenoxyalklpyridazines and intermediates therefor
  申请人：Sterling Winthrop Inc.

  公开号：US05514679A1

  公开（公告）日：1996-05-07

  Compounds of the formula ##STR1## wherein: R.sub.1 and R.sub.2 are independently hydrogen, halo, alkyl, alkenyl, alkoxy, hydroxy, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, alkylthioalkynyl, hydroxyalkoxy, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, amino, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy or cyanomethyl, nitro, difluoromethyl, trifluoromethyl or cyano; Y is alkylene of 3 to 9 carbon atoms; R.sub.3 and R.sub.4 are independently hydrogen, alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkanoyl, alkanoyloxy, alkylsulfinylalkyl, alkylsulfonylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy, cyanomethyl, fluoroalkyl, cyano, phenyl, alkynyl, alkene, or halo; R.sub.5 is alkoxycarbonyl, alkyltetrazolyl, phenyl or a heterocycle; or a pharmaceutically acceptable acid addition salts thereof; N-oxides thereof, are useful as antipirconaviral agents.

  式为##STR1##的化合物，其中：R.sub.1和R.sub.2独立地是氢、卤素、烷基、烯基、烷氧基、羟基、羟基烷基、羟基卤代烷基、烷氧基烷基、烷硫烯基、羟基烷氧基、烷硫基烷基、烷基磺酰基烷基、烷基磺基烷基、氨基、氨基烷基、烷基氨基烷基、二烷基氨基烷基、烷氧羰基、羧基或氰甲基、硝基、二氟甲基、三氟甲基或氰基；Y为3至9个碳原子的烷基；R.sub.3和R.sub.4独立地是氢、烷基、烷氧基、羟基、环烷基、羟基烷基、羟基卤代烷基、烷氧基烷基、羟基烷氧基、烷硫基烷基、烷酰基、烷酰氧基、烷基磺酰基烷基、烷基磺基烷基、氨基烷基、烷基氨基烷基、二烷基氨基烷基、烷氧羰基、羧基、氰甲基、氟烷基、氰基、苯基、炔基、烯烃或卤素；R.sub.5为烷氧羰基、烷基四唑基、苯基或杂环；或其药学上可接受的酸盐；其N-氧化物可用作抗逆转录病毒药物。
• Therapeutic phenoxyalkylpyridazines and intermediates therefor
  申请人：Sanofi, S.A.

  公开号：US05665763A1

  公开（公告）日：1997-09-09

  Compounds of the formula ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the specification, Y is alkylene of 3 to 9 carbon atoms, R.sub.5 is alkoxycarbonyl, alkyltetrazolyl, phenyl or a heterocycle chosen from benzoxazolyl, benzathiazolyl, thiadiazolyl, imidazolyl, dihydroimidazolyl, oxazolyl, thiazolyl, oxadiazolyl, pyrazolyl, oxazolinyl, isoxazolyl, isothiazolyl, furyl, triazolyl, thiophenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or any of the above substituted with alkyl, alkoxyalkyl, cycloalkyl, halo alkyl, hydroxyalkyl, alkoxy, hydroxy, halo, furyl, thienyl, fluoroalkyl; or a pharmaceutically acceptable acid addition salts thereof; N-oxides thereof, are useful as antipirconaviral agents.

  式子为##STR1##的化合物，其中：R.sub.1、R.sub.2、R.sub.3和R.sub.4如规范中所定义，Y为3至9个碳原子的烷基，R.sub.5为烷氧羰基，烷基四唑基，苯基或从苯并噁唑基，苯并噻唑基，噻二唑基，咪唑基，二氢咪唑基，噁唑基，噻唑基，噁二唑基，吡唑基，噁唑啉基，异噁唑基，异噻唑基，呋喃基，三唑基，噻吩基，氟烷基取代的上述任何一个杂环；或其药学上可接受的酸盐；其N-氧化物，可用作抗病毒药剂。