1-(3,4-dimethoxy-phenyl)-but-3-yn-1-ol | 91496-51-4

• 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: 1-(3,4-dimethoxy-phenyl)-but-3-yn-1-ol
• 英文别名: 1-(3,4-Dimethoxy-phenyl)-but-3-in-1-ol；1-(3,4-Dimethoxyphenyl)but-3-yn-1-ol
• CAS: 91496-51-4
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: ZIIMICYYJLMSGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  128-132 °C(Press: 0.1 Torr)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxy-phenyl)-but-3-yn-1-ol 在 Jones reagent 作用下， 以 丙酮 为溶剂， 生成 1-(3,4-Dimethoxy-phenyl)-buta-2,3-dien-1-one
  参考文献：
  名称：

  1,2-烯丙基酮的串联反应导致取代的苯和α，β-不饱和腈

  摘要：

  一锅双迈克尔加成反应/分子内羟醛反应/氰基乙酸酯对1,2-烯酮的脱羧作用为高效官能化的苯提供了一种有效而便捷的方法。用2-取代的氰基乙酸酯，反应通过不同的串联过程进行，以有效地得到α，β-不饱和腈。

  DOI：

  10.1021/ol201789z
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 3-溴丙炔 在 magnesium 、 mercury dichloride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 1-(3,4-dimethoxy-phenyl)-but-3-yn-1-ol
  参考文献：
  名称：

  金催化均丙基醚的氧化重排合成环丁酮

  摘要：

  在金催化剂和8-乙基喹啉N-氧化物的存在下，带有富电子芳环或烯基的均丙基醚可以平稳地转化为顺式-环丁酮。事实证明，α-氧代金类胡萝卜素是关键的中间体，它可以演变成叶立德。

  DOI：

  10.1002/adsc.201300227

文献信息

• Isomerizations on silica gel: Synthesis of allenyl ketones and the first Nazarov cyclizations of vinyl allenyl ketones
  作者：A Stephen、K Hashmi、Jan W Bats、Ji-Hyun Choi、Lothar Schwarz

  DOI：10.1016/s0040-4039(98)01619-0

  日期：1998.10

  chromatographic workup of crude, terminal propargyl ketones 5 on silica gel directly leads to terminal allenyl ketones 6. When the other substituent on 5 was electron-rich, 7 was observed as side-product. If the other substituent on 5 was electron-poor, the isomeric 1-propynyl ketone 8 was the side-product. Chromatography of the crude propargyl vinyl ketones 10 on silica gel delivers the products of a Nazarov

  进行Dess-Martin氧化，然后在硅胶上进行粗制的末端炔丙基酮5的色谱处理，直接制得末端烯基酮6。当5上的另一个取代基富含电子时，观察到7为副产物。如果5上的另一个取代基是电子贫的，则异构的1-丙炔基酮8是副产物。在硅胶上色谱分离粗制炔丙基乙烯基酮10，得到纳扎罗夫环化产物。
• Zinc barbier reaction of propargyl halides in water
  作者：Lothar W. Bieber、Margarete F. da Silva、Rosenildo C. da Costa、Lília O.S. Silva

  DOI：10.1016/s0040-4039(98)00641-8

  日期：1998.5

  The reaction of propargyl halides and carbonyl compounds with zinc powder proceeds in concentrated aqueous salt solutions affording with high selectivity homopropargylic alcohols. Preparatively useful yields are obtained with aromatic and aliphatic aldehydes. Ketones and 2-hydroxybenzaldehydes react partially. A surface process of two SET is discussed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Synthesis of 1,1-Disubstituted Alkenes via a Ru-Catalyzed Addition
  作者：Barry M. Trost、Anthony B. Pinkerton、F. Dean Toste、Martin Sperrle

  DOI：10.1021/ja012009m

  日期：2001.12.19

  The synthesis of 1,1-disubstituted alkenes typically involves reactions that lack atom economy such as olefination protocols. The use of various ruthenium complexes to effect the addition of terminal alkynes to alkenes is explored as an atom economical strategy. Two new ruthenium complexes have been discovered that effect this reaction at ambient temperature, cyclopentadienyl ruthenium (triphenylphosphine) camphorsulfonate and cyclopentadienylruthenium tris(acetonitrile) hexafluorophosphate. Using these complexes as catalysts, reactions proceed at ambient temperature in acetone or DMF, respectively. Regioselectivity favoring the formation of a 1,1-disubstituted over a 1,2-disubstituted alkene typically ranges from 9:1 to > 25: 1. The reaction demonstrates extraordinary chemoselectivity-even di- and trisubstituted alkenes such as present in the products do not compete with the starting monosubstituted alkene. Free hydroxyl groups a well as silyl and PMB ethers are tolerated as are ketones, esters, and amides. The mechanism of the reaction is believed to invoke formation of a metallacyclopentene. To account for the chemo- and regioselectivity, the initial formation of the metallacycle is believed to be reversible. While formation of the 2,5-disubstituted ruthenacyclopentene, which produces the linear product, is believed to be kinetically preferred. the rate of beta -hydrogen elimination from the 2,4-disubstituted ruthenacyclopentene, which produces the branched product, is believed to be faster. Thus, the competition between the rate of beta -hydrogen elimination and cycloreversion rationalizes the results.
• Ruthenium-Catalyzed Cycloisomerization−Oxidation of Homopropargyl Alcohols. A New Access to γ-Butyrolactones
  作者：Barry M. Trost、Young H. Rhee

  DOI：10.1021/ja992013m

  日期：1999.12.1

  Vinylidenemetal species, which readily form from terminal alkynes under mild conditions, have rarely been utilized as reactive intermediates in a catalytic cycle. The conversion of homopropargyl alcohols via such intermediates to metal-complexed oxacarbenes led to the development of an "oxidant" compatible with a ruthenium complex capable of performing the cycloisomerization, that would convert them to lactones. None of the oxidants known to stoichiometrically convert isolated metallooxacarbenes to esters are effective. The unconventional "oxidants", N-hydroxyimides, proved to be capable of effecting the desired transformation, with N-hydroxysuccinimide being the "oxidant" of choice. The procedure of choice employs cyclopentadienyl (1,4-cyclooctadiene) ruthenium chloride and trifuryl phosphine as the precatalyst in the presence of tetra-n-butylammonium bromide or hexafluorophosphate with N-hydroxysuccinimide as the oxidant in DMF-water at 95 degrees. In this way, a wide diversity of homopropargyl alcohols were converted to gamma-butyrolactones with excellent chemoselectivity. Lactones synthesized include an intermediate toward a platelet aggregation inhibitor, a fruit flavor principle, an inhibitor of binding of phorbol esters to PKC-alpha, a tobacco constituent, a wood constituent (quercus lactone), an aldosterone antagonist (spironolactone) precursor, and an acetogenin known for pesticidal and antitumor activities (muricatacin).
• The Prevalence of Daytime Napping and Its Relationship to Nighttime Sleep
  作者：June J. Pilcher、Kristin R. Michalowski、Renee D. Carrigan

  DOI：10.1080/08964280109595773

  日期：2001.1

  Many healthy adults report daytime napping. Surprisingly few studies, however have examined spontaneous napping behavior especially very short naps, in healthy adults. The authors examined the prevalence of power naps (lasting less than 20 minutes) and longer naps (20 minutes or more) and their effects on nighttime sleep in a group of healthy young and middle-aged adults. The young and middle-aged adults reported very similar sleep and napping patterns, with approximately 74% of the participants in both groups reporting they had napped during a 7-day sleep-log period. Almost half of the participants reported that the average nap lasted less than 20 minutes. A multivariant analysis of variance (MANOVA) found no significant differences between the no-nap and the power-nap or long-nap groups in sleep quantity or quality for either age group. The current data suggested that power napping occurs frequently in healthy adults and that spontaneous napping does not negatively affect nighttime sleep.