2-(buta-1,2-dienyloxy)tetrahydro-2H-pyran | 1085339-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-(buta-1,2-dienyloxy)tetrahydro-2H-pyran
• CAS: 1085339-80-5
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: FYIWUUKCGDBGPR-UHFFFAOYSA-N

物化性质

• 沸点：
  249.1±20.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-碘代甲苯 、 2-(buta-1,2-dienyloxy)tetrahydro-2H-pyran 在 palladium diacetate sodium acetate 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以68%的产率得到(E)-2-o-tolylbut-2-enal
  参考文献：
  名称：

  Palladium-catalysed Heck reaction on 1,2-dien-1-ols: a stereoselective synthesis of α-arylated α,β-unsaturated aldehydes

  摘要：

  A new methodology for preparing alpha-arylated alpha,beta-unsaturated aldehydes is reported. The starting materials are all commercially available alkyn-1-ols (la-c) that have been easily isomerised to the corresponding allenes (2a-c). The key step is the Heck coupling of the 1,2-dien-1-ols with a series of iodo- and bromoarene. The products have been synthesised in good yields, and the reactions were carried out under very mild conditions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.081
• 作为产物：
  描述：

  2-(but-2-ynyloxy)-tetrahydro-2H-pyran 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以60%的产率得到2-(buta-1,2-dienyloxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Heck reaction on protected 3-alkyl-1,2-dien-1-ols: an approach to substituted 3-alkenylindoles, 2-alkoxy-3-alkylidene-2,3-dihydrobenzofuranes and -indolidines

  摘要：

  利用无磷环化反应制备了取代的 3-烯基吲哚、2-烷氧基-3-亚烷基-2,3-二氢苯并呋喃和吲哚啉，收率从良好到极佳。这是通过受保护的 3-烷基-1,2-二烯醇与邻碘苯酚或受保护的邻碘苯胺反应实现的。根据参与环化过程的杂原子的电子供能特性，可以得到两种不同的杂环骨架。

  DOI：

  10.1039/b925550h

文献信息

• Palladium-catalysed Heck reaction on 1,2-dien-1-ols: a stereoselective synthesis of α-arylated α,β-unsaturated aldehydes
  作者：Annamaria Deagostino、Cristina Prandi、Antonio Toppino、Paolo Venturello

  DOI：10.1016/j.tet.2008.08.081

  日期：2008.11

  A new methodology for preparing alpha-arylated alpha,beta-unsaturated aldehydes is reported. The starting materials are all commercially available alkyn-1-ols (la-c) that have been easily isomerised to the corresponding allenes (2a-c). The key step is the Heck coupling of the 1,2-dien-1-ols with a series of iodo- and bromoarene. The products have been synthesised in good yields, and the reactions were carried out under very mild conditions. (C) 2008 Elsevier Ltd. All rights reserved.
• Heck reaction on protected 3-alkyl-1,2-dien-1-ols: an approach to substituted 3-alkenylindoles, 2-alkoxy-3-alkylidene-2,3-dihydrobenzofuranes and -indolidines
  作者：Tommaso Boi、Annamaria Deagostino、Cristina Prandi、Silvia Tabasso、Antonio Toppino、Paolo Venturello

  DOI：10.1039/b925550h

  日期：——

  A phosphine-free annulation reaction has been exploited for the preparation of substituted 3-alkenylindoles, 2-alkoxy-3-alkylidene-2,3-dihydrobenzofuranes and -indolidines in good to excellent yields. This has been done by reaction of protected 3-alkyl-1,2-dienols with o-iodophenols or protected o-iodoanilines. Two different heterocyclic skeletons were obtained, depending on the electron-donating properties of the heteroatom involved in the annulation process.

  利用无磷环化反应制备了取代的 3-烯基吲哚、2-烷氧基-3-亚烷基-2,3-二氢苯并呋喃和吲哚啉，收率从良好到极佳。这是通过受保护的 3-烷基-1,2-二烯醇与邻碘苯酚或受保护的邻碘苯胺反应实现的。根据参与环化过程的杂原子的电子供能特性，可以得到两种不同的杂环骨架。