1-(2,4-dimethylphenyl)oxy-4-chloro-but-2-yne | 124067-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2,4-dimethylphenyl)oxy-4-chloro-but-2-yne
• 英文别名: 4-chloro-1-(2,4-dimethylphenyloxy)but-2-yne；1-[(4-Chlorobut-2-yn-1-yl)oxy]-2,4-dimethylbenzene；1-(4-chlorobut-2-ynoxy)-2,4-dimethylbenzene
• CAS: 124067-85-2
• 化学式: C₁₂H₁₃ClO
• 分子量: 208.688
• InChiKey: HQYKJKBOVOVXPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2,4-dimethylphenyl)oxy-4-chloro-but-2-yne 在 potassium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 24.0h， 生成 [2-[(2,4-dimethylphenoxy)methyl]-3,6-dimethyl-7-oxopyrrolo[3,2-f]quinolin-1-yl]methyl 3-chlorobenzoate
  参考文献：
  名称：

  Majumdar, K. C.; Birwas, P.; Jama, G. H., Journal of Chemical Research, Miniprint, 1997, # 9, p. 2068 - 2079

  摘要：

  DOI：

文献信息

• One-pot synthesis of 2-aryloxymethyl-1-cyanomethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline via rearrangement of the N-oxide from 1-aryloxy-4-tetrahydro-1-quinolylbut-2-yne
  作者：Krishna C. Majumdar、Shital K. Chattopadhyay、Abu T. Khan

  DOI：10.1039/p19890001285

  日期：——

  1-Aryloxy-4-tetrahydro-1 -quinoylbut-2-yne (1), on treatment with m-chloroperbenzoic acid in dichloromethane at room temperature for 12 h, rearranged to give the bispyrroloquinoline derivative (3) in 30–45% yield. Addition of aqueous potassium cyanide to the intermediate (not isolated) gave the title compound (5) in 55–75% yield.

  1-芳氧基-4-四氢-1- -quinoylbut -2-炔（1），与治疗米氯过苯甲酸在二氯甲烷中在室温下搅拌12小时，重排，得到bispyrroloquinoline衍生物（3中30-45％的产率） 。在中间体（未分离的）中加氰化钾水溶液，得到标题化合物（5），产率为55-75％。
• Regioselective unusual formation of spirocyclic 4-{3′-benzo(2′,3′-dihydro)furo}-9-methyl-2,3,9-trihydrothiopyrano [2,3-<i>b</i>]indole by acid-catalyzed reaction of enol ethers
  作者：K. C. Majumdar、S. Alam、B. Chattopadhyay

  DOI：10.1002/jhet.31

  日期：2009.1

  3′-dihydro)furo}-9-methyl-2,3,9-trihydrothiopyrano[2,3-b]indoles are regioselectively synthesized by treating suitable enol ethers, 4-aryloxymethylene-9-methyl-2,3,9-trihydrothio-pyrano[2,3-b]indoles with H2SO4 in dichloromethane-methanol-water. The substrates for the aforesaid reaction are in turn synthesized by the thio-Claisen rearrangement of 2-(4′-aryloxybut-2′-ynylthio)-1-methylindoles. J. Heterocyclic Chem.

  通过处理合适的烯醇醚，区域选择性地合成螺环4- 3'-苯并（2'，3'-二氢）呋喃} -9-甲基-2,3,9-三氢噻喃并[2,3- b ]吲哚。在二氯甲烷-甲醇-水中，具有H 2 SO 4的芳氧基亚甲基-9-甲基-2,3,9-三氢硫代吡喃并[2,3- b ]吲哚。上述反应的底物又通过2-（4'-芳氧基丁-2'-炔硫基）-1-甲基吲哚的硫代-克莱森重排而合成。杂环化学杂志，46，62（2009）。
• Stereoselective Synthesis of Tricyclic Pyranoxepin Derivatives by Ruthenium-Catalyzed Enyne Metathesis/Diels-Alder Reaction
  作者：K. Majumdar、H. Rahaman、S. Muhuri、B. Roy

  DOI：10.1055/s-2006-926238

  日期：——

  Synthesis of tricyclic oxepin-annulated pyrone derivatives has been achieved by the ring-closing enyne metathesis using the first-generation Grubbs' catalyst under a nitrogen atmosphere. The Diels-Alder reaction of these cyclized products with the dienophile proceeded smoothly to afford the tricyclic compounds in excellent yield.

  在氮气氛下使用第一代 Grubbs 催化剂通过闭环烯炔复分解实现了三环 oxepin 环化吡喃酮衍生物的合成。这些环化产物与亲二烯体的狄尔斯-阿尔德反应顺利进行，以优异的收率得到三环化合物。
• Regioselective synthesis of biologically interesting pentacyclic polyheterocycles by sequential thio-Claisen and AlCl₃ catalyzed oxy-Claisen rearrangement of 4-(4′-aryloxybut-2′-ynylthio)-1-phenyl-1,8-naphthyridin-2(1<i>H</i>)-one
  作者：K C Majumdar、R Islam

  DOI：10.1139/v06-174

  日期：2006.12.1

  A number of 4-aryloxymethyl-6-phenyl-2H-thiopyrano[3,2-c][1,8]naphthyridin-5(6H)-ones were regio selectively synthesized in 82%–95% yields by the thermal Claisen rearrangement of 4-(4′-aryloxybut-2...

  通过热克莱森重排以 82%–95% 的产率选择性地合成了许多 4-芳氧基甲基-6-苯基-2H-噻喃[3,2-c][1,8]萘啶-5(6H)-ones 4-(4'-芳氧基丁-2...
• Synthesis of Bioactive Heterocycles: Sigmatropic Rearrangements of 1,3-Dimethyl-6-[methyl(4-aryloxybut-2-ynyl)amino]pyrimidine-2,4(1<b><i>H</i></b>,3<i>H</i>)-diones
  作者：K. Majumdar、T. Bhattacharyya

  DOI：10.1055/s-2001-16097

  日期：——

  A number of 1,3-dimethyl-6-[methyl(4-aryloxybut-2-ynyl)amino]pyrimidine-2,4(1H,3H)-diones 4a-i were synthesised in 69 to 80% yields by the reaction of 6-chloro-1,3-dimethyluracil (6-chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-diones) and 1-aryloxy-4-N-methylaminobut-2-yne in refluxing ethanol for 12 hours. The tertiary amines 4a-i were then heated in refluxing 1,2-dichlorobenzene for 17 hours to give 5-[(E)-aryloxymethylidene]-1,3,8-trimethyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-2,4(1H,3H)-diones 5a-i in 55 to 75% yields.

  通过 6-氯-1,3-二甲基脲嘧啶（6-氯-1,3-二甲基嘧啶-2,4(1H,3H)-二酮）和 1-芳氧基-4-N-甲基氨基丁-2-炔反应，合成了一些 1,3-二甲基-6-[甲基(4-芳氧基丁-2-炔基)氨基]嘧啶-2,4(1H,3H)-二酮 4a-i，收率为 69%至 80%、3-二甲基尿嘧啶（6-氯-1,3-二甲基嘧啶-2,4(1H,3H)-二酮）和 1-芳氧基-4-N-甲基氨基丁-2-炔在回流乙醇中反应 12 小时，合成了 4a-i，产率为 69% 至 80%。然后将叔胺 4a-i 在回流的 1,2 二氯苯中加热 17 小时，得到 5-[(E)-芳氧基亚甲基]-1,3,8-三甲基-5,6,7,8-四氢吡啶并[2,3-d]嘧啶-2,4(1H,3H)-二酮 5a-i，收率为 55% 至 75%。