2-((tetrahydro-2H-pyran-2-yloxy)methyl)indole | 658701-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-((tetrahydro-2H-pyran-2-yloxy)methyl)indole
• 英文别名: 2-(oxan-2-yloxymethyl)-1H-indole
• CAS: 658701-98-5
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: VTCDDEBFWJRKAM-UHFFFAOYSA-N

物化性质

• 沸点：
  406.1±40.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  哌喃 、 2-碘乙酰苯胺 在 Pd(II)-NaY zeolite 、 caesium carbonate 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以69%的产率得到2-((tetrahydro-2H-pyran-2-yloxy)methyl)indole
  参考文献：
  名称：

  Pd–NaY沸石催化剂通过钯催化杂环化反应合成2-取代的吲哚

  摘要：

  通过邻位碘苯胺和末端炔烃与Pd（II）-NaY沸石催化剂的一锅法反应，制得各种2-取代的吲哚。产物的形成很大程度上取决于溶剂，碱和反应温度。再循环的催化剂在杂环化反应中显示出良好的可重复使用性。

  DOI：

  10.1016/j.tetlet.2003.11.075

文献信息

• Assembly of Conjugated Enynes and Substituted Indoles via CuI/Amino Acid-Catalyzed Coupling of 1-Alkynes with Vinyl Iodides and 2-Bromotrifluoroacetanilides
  作者：Feng Liu、Dawei Ma

  DOI：10.1021/jo070547x

  日期：2007.6.1

  Cross-coupling of 1-alkynes with vinyl iodides occurs at 80 degrees C in dioxane catalyzed by CuI/N,N-dimethylglycine to afford conjugated enynes in good to excellent yields. Heating a mixture of 2-bromotrifluoroacetanilide, 1-alkyne, 2 mol % of CuI, 6 mol % of L-proline, and K2CO3 in DMF at 80 degrees C leads to the formation of the corresponding indole. This conversion involves a CuI/L-proline-catalyzed coupling between aryl bromide and the 1-alkyne followed by a CuI-mediated cyclization process. An ortho-substituent effect directed by NHCOCF3 enables the reaction to proceed under these mild conditions. Both aryl acetylenes and O-protected propargyl alcohol can be applied, leading to 5-, 6-, or 7-substituted 2-aryl and protected 2-hydroxymethyl indoles in good yields. With simple aliphatic alkynes, however, lower yields were observed.
• Synthesis of 2-substituted indoles by palladium-catalyzed heteroannulation with Pd–NaY zeolite catalysts
  作者：Ki Bum Hong、Chul Wee Lee、Eul Kgun Yum

  DOI：10.1016/j.tetlet.2003.11.075

  日期：2004.1

  Various 2-substituted indoles were prepared by heteroannulation of o-iodoanilines and terminal alkynes in a one-pot reaction with a Pd(II)–NaY zeolite catalyst. The product formation largely depended on the solvent, base, and reaction temperature. The recycled catalyst showed good reusability in the heteroannulation reaction.

  通过邻位碘苯胺和末端炔烃与Pd（II）-NaY沸石催化剂的一锅法反应，制得各种2-取代的吲哚。产物的形成很大程度上取决于溶剂，碱和反应温度。再循环的催化剂在杂环化反应中显示出良好的可重复使用性。