(epoxy-2,3 propyl)-2 tetrahydropyranne | 104727-83-5

• 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: (epoxy-2,3 propyl)-2 tetrahydropyranne
• 英文别名: 2-(Oxiran-2-ylmethyl)oxane
• CAS: 104727-83-5
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: WUFSZZRVLJRIMA-UHFFFAOYSA-N

物化性质

• 沸点：
  100-102 °C(Press: 25 Torr)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (epoxy-2,3 propyl)-2 tetrahydropyranne 、 苯乙炔 在 三甲基镓 正丁基锂 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 5.0h， 以77%的产率得到5-Phenyl-1-(tetrahydro-pyran-2-yl)-pent-4-yn-2-ol
  参考文献：
  名称：

  Remarkable catalytic activity of Me3Ga in the alkylation of hetero-substituted epoxides with alkynyllithiums

  摘要：

  Regio- and stereoselective ring-opening reaction of hetero-substituted epoxides with alkynyllithiums can be catalyzed by Me3Ga with remarkable efficiency at 0 similar to 20 degrees C via pentacoordinate chelate-type complex. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01096-5
• 作为产物：
  描述：

  2-甲氧基四氢吡喃 在 三氟甲磺酸三甲基硅酯 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 (epoxy-2,3 propyl)-2 tetrahydropyranne
  参考文献：
  名称：

  Pentacoordinate Organoaluminum Chemistry:  Catalytic Efficiency of Me₃Al in the Epoxide Cleavage with Alkynyllithiums

  摘要：

  A new and highly effective catalytic method for epoxide alkynylations has been developed that involves the chelation-controlled alkylation of heterosubstituted epoxides with Me3Al via pentacoordinate organoalluminum complexes by taking advantage of the exceedingly high affinity of aluminum to oxygen. For example, reaction of epoxy ether, (l-benzyloxy)-3-butene oxide (1), in toluene with PhC=CLi under the influence of catalytic Me3Al (10 mol%) proceeded smoothly at O degrees C for 5 h to furnish the alkynylation product, l-(benzyloxy)-6-phenylhex-5-yn-3-ol, in 76% yield [cf. 3% without Me3Al catalyst; 78% with stoichiometric Me3Al under similar conditions]. This represents the first catalytic procedure for the amphiphilic alkylation of epoxides. The participation of pentacoordinate Me3Al complexes of epoxy ethers of type 1 is emphasized by comparing the reactivity with the corresponding simple epoxide, 5-phenyl-l-pentene oxide, which was not susceptible to nucleophile attack of PhC=CLi with catalytic Me3A1 under similar conditions. The pentacoordinate complex formation of Me3Al with epoxy ether 1 is characterized by low-temperature C-13 and Al-27 NMR spectroscopy. This approach is also applicable to the selective alkynylation of tosyl aziridines with adjacent ether functionality, which provides a promising method for amino alcohol synthesis.

  DOI：

  10.1021/ja9842464

文献信息

• Deplacements homolytiques intramoleculaires
  作者：B. Maillard、E. Montaudon、F. Rakotomanana、M.J. Bourgeois

  DOI：10.1016/s0040-4020(01)96750-x

  日期：1985.1

  of allyl t-butyl peroxide in cyclohexane and tetrahydrofuran shows that an important induced decomposition of the peroxide occurs by the addition of radicals derived from the solvent, to the peroxide double bond, followed by an intramolecular homolytic displacement of the t-butoxyl group. Such a reaction is a 2,3-epoxypropanation of the solvent in which the initiator is decomposed. The reaction is

  烯丙基叔丁基过氧化物在环己烷和四氢呋喃中热解的产物分析表明，过氧化物的重要诱导分解是通过将源自溶剂的自由基添加到过氧化物双键中，然后将t的分子内均质置换而完成的。 -丁氧基。该反应是引发剂分解的溶剂的2，3-环氧丙烷化。通过使用其他醚和环烷烃作为溶剂，表明该反应是一般的。
• MAILLARD, B.;MONTAUDON, E.;RAKOTOMANANA, F.;BOURGEOIS, M. J., TETRAHEDRON, 1985, 41, N 21, 5039-5043
  作者：MAILLARD, B.、MONTAUDON, E.、RAKOTOMANANA, F.、BOURGEOIS, M. J.

  DOI：——

  日期：——
• Pentacoordinate Organoaluminum Chemistry:  Catalytic Efficiency of Me₃Al in the Epoxide Cleavage with Alkynyllithiums
  作者：Takashi Ooi、Naoko Kagoshima、Hayato Ichikawa、Keiji Maruoka

  DOI：10.1021/ja9842464

  日期：1999.4.1

  A new and highly effective catalytic method for epoxide alkynylations has been developed that involves the chelation-controlled alkylation of heterosubstituted epoxides with Me3Al via pentacoordinate organoalluminum complexes by taking advantage of the exceedingly high affinity of aluminum to oxygen. For example, reaction of epoxy ether, (l-benzyloxy)-3-butene oxide (1), in toluene with PhC=CLi under the influence of catalytic Me3Al (10 mol%) proceeded smoothly at O degrees C for 5 h to furnish the alkynylation product, l-(benzyloxy)-6-phenylhex-5-yn-3-ol, in 76% yield [cf. 3% without Me3Al catalyst; 78% with stoichiometric Me3Al under similar conditions]. This represents the first catalytic procedure for the amphiphilic alkylation of epoxides. The participation of pentacoordinate Me3Al complexes of epoxy ethers of type 1 is emphasized by comparing the reactivity with the corresponding simple epoxide, 5-phenyl-l-pentene oxide, which was not susceptible to nucleophile attack of PhC=CLi with catalytic Me3A1 under similar conditions. The pentacoordinate complex formation of Me3Al with epoxy ether 1 is characterized by low-temperature C-13 and Al-27 NMR spectroscopy. This approach is also applicable to the selective alkynylation of tosyl aziridines with adjacent ether functionality, which provides a promising method for amino alcohol synthesis.
• Remarkable catalytic activity of Me3Ga in the alkylation of hetero-substituted epoxides with alkynyllithiums
  作者：Takashi Ooi、Junko Morikawa、Hayato Ichikawa、Keiji Maruoka

  DOI：10.1016/s0040-4039(99)01096-5

  日期：1999.8

  Regio- and stereoselective ring-opening reaction of hetero-substituted epoxides with alkynyllithiums can be catalyzed by Me3Ga with remarkable efficiency at 0 similar to 20 degrees C via pentacoordinate chelate-type complex. (C) 1999 Elsevier Science Ltd. All rights reserved.

表征谱图