3-Prop-2-ynoxybut-1-ene | 109930-19-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Prop-2-ynoxybut-1-ene
• CAS: 109930-19-0
• 化学式: C₇H₁₀O
• 分子量: 110.156
• InChiKey: QOCFGNMLOJUGNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  127.7±15.0 °C(Predicted)
• 密度：
  0.849±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  3-Prop-2-ynoxybut-1-ene 在 dicobalt octacarbonyl 六甲基磷酰三胺 、 正丁基锂 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正庚烷 为溶剂， 反应 8.08h， 生成 trans-6-tert-Butylthio-3-methyl-3a,4-dihydro-1H,3H-cyclopenta[c]furan-5-one
  参考文献：
  名称：

  (Alkylthio)alkynes as Addends in the Co(0) Catalyzed Intramolecular Pauson-Khand Reaction. Substituent Driven Enhancements of Annulation Efficiency and Stereoselectivity

  摘要：

  与末端炔烃相比，（甲硫基）炔烃通常是热促进的、由Co2(CO)8催化的烯炔和炔炔的Pauson-Khand反应的优越底物，能够提供更高产率和增强的非对映选择性。还透露了依赖于使用2,2,2-三氟乙醇作为共溶剂的产率改善，以及对（乙氧基）炔烃的内选择性的明显偏好。

  DOI：

  10.1055/s-2000-6301
• 作为产物：
  描述：

  3-butene-2-ol, sodium salt 、 3-溴丙炔 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 3-Prop-2-ynoxybut-1-ene
  参考文献：
  名称：

  Substituent effects in the aliphatic Claisen rearrangement of substituted (1-methyl-3-oxahexa-1,5-dienyl)amines: synthesis of substituted 2-aminopent-4-enals. Alternative [1,3]-sigmatropic shifts in related aromatic systems

  摘要：

  DOI：

  10.1021/jo00232a024

文献信息

• An Improved Method for the Synthesis of 1-lodoalkynes
  作者：José Barluenga、José M. González、Miguel A. Rodríguez、Pedro J. Campos、Gregorio Asensio

  DOI：10.1055/s-1987-28042

  日期：——

  A simple and general one-pot procedure for the synthesis of 1-iodoalkynes is described based on the reaction of terminal acetylenes with bis(pyridine)iodine(I) tetrafluoroborate in the presence of sodium methoxide. The method now reported is superior to the literature procedures in scope, handling, and often yield.

  本文描述了一种简单通用的合成1-碘代炔烃的一锅法，该方法基于端基乙炔与双吡啶碘（I）四氟硼酸盐在甲醇钠存在下的反应。所报道的方法在应用范围、操作便利性以及产率方面通常优于现有文献中的方法。
• Catalytic and Oxidative Methoxymercuration of Terminal Alkynes: Syntheses of 2-Methoxy-1-alkenes and 2-Methoxy-acrolein Acetals
  作者：José Barluenga、Fernando Aznar、Miguel Bayod

  DOI：10.1055/s-1988-27495

  日期：——

  2-Methoxy-1-alkenes 2 are easily obtained by reaction of a variety of 1-alkynes with an excess of methanol in the presence of triethylamine and catalytic amounts of mercury(II) chloride. By changing the molar ratio of the reagents and increasing the reaction time, propargyl ethers undergo a further oxidative process to give the 2-methoxyacrolein acetals 3.

  2-甲氧基-1-烯烃 2 可以通过将多种 1-炔烃与过量甲醇在三乙胺和催化量的氯化汞存在下反应来轻松获得。通过改变试剂的摩尔比并延长反应时间，丙炔醚进一步经历氧化过程，生成 2-甲氧基丙烯醛缩醛 3。
• Adsorption effects on the efficiency of cobalt-mediated cyclizations of allylpropargyl ethers into derivatives of 3-oxabicyclo[3.3.0]oct-5-en-7-one
  作者：S.O. Simonian、W.A. Smit、A.S. Gybin、A.S. Shashkov、G.S. Mikaelian、V.A. Tarasov、I.I. Ibragimov、R. Caple、D.E. Froen

  DOI：10.1016/s0040-4039(00)84228-8

  日期：1986.1

  in an adsorbed state under oxygen is shown to be a mild and general method for promoting a Khand-Pauson cyclization of dicobalt hexacarbonyl complexes of allylpropargyl ethers into derivatives of 3-oxabicyclo[3.3.0]oct-5-en-7-one.

  氧在吸附状态下的热解是促进烯丙基炔丙基醚的二钴六羰基配合物的Khand-Pauson环化为3-氧杂双环[3.3.0] oct-5-en-7-one的衍生物的温和且通用的方法。 。
• Cyclization of Dicobalthexacarbonyl Complexes of Allyl Propargyl Ethers on the Surface of Chromatography Adsorbents. A Convenient Method for the Preparation of Substituted 3-Oxabicyclo[3.3.0]oct-5-en-7-one and 4-Hydroxymethyl-2-cyclopenten-1-one Derivatives from Common Precursors
  作者：W. A. Smit、S. O. Simonyan、V. A. Tarasov、G. S. Mikaelian、A. S. Gybin、I. I. Ibragimov、R. Caple、D. Froen、A. Kreager

  DOI：10.1055/s-1989-27296

  日期：——

  Allyl propargyl ethers serve as valuable precursors for short and efficient syntheses of the title compounds via an intramolecular [2 + 2 + 1] Khand-Pauson cyclization under the novel procedure of adsorption-promoted (dry state) conditions.

  丙烯基丙炔醚作为有价值的前体，通过一种新颖的吸附促进（干态）条件下的分子内 [2 + 2 + 1] Khand-Pauson 环化反应，为标题化合物的简短和高效合成提供了途径。
• Computationally Designed and Experimentally Confirmed Diastereoselective Rhodium-Catalyzed Pauson−Khand Reaction at Room Temperature
  作者：Mu-Hyun Baik、Shivnath Mazumder、Paolo Ricci、James R. Sawyer、Ye-Geun Song、Huijun Wang、P. Andrew Evans

  DOI：10.1021/ja107895g

  日期：2011.5.25

  The computational analysis of the rhodium-catalyzed Pauson-Khand reaction indicates that the key transition state is highly charge-polarized, wherein different diastereoisomers have distinctively different charge polarization patterns. Experimental studies demonstrate that chloro-enynes provide the optimal sigma-electron-withdrawing group to promote polarization and thereby reduce the activation barrier to provide a highly diastereoselective reaction at room temperature.