3-(naphthalen-1-yl)but-3-en-2-ol | 141171-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(naphthalen-1-yl)but-3-en-2-ol
• 英文别名: 3-(1-naphthyl)-3-buten-1-ol；3-Naphthalen-1-ylbut-3-en-2-ol
• CAS: 141171-89-3
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: SDLUMBBJNQSBBE-UHFFFAOYSA-N

物化性质

• 沸点：
  355.8±11.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  丙酸酐 、 3-(naphthalen-1-yl)but-3-en-2-ol 在 C₂₇H₂₀N₂ 、 N,N-二异丙基乙胺 作用下， 以 甲基叔丁基醚 、 氯仿 为溶剂， 反应 24.08h， 以48.3%的产率得到
  参考文献：
  名称：

  Nonenzymatic kinetic resolution of α-aryl substituted allylic alcohols catalyzed by acyl transfer catalyst Np-PIQ

  摘要：

  Chiral alpha-aryl substituted allylic alcohols are important versatile synthetic intermediates. We report here an effective nonenzymatic kinetic resolution of racemic alpha-aryl substituted allylic alcohols by introducing different aryl groups with acyl transfer catalyst Np-PIQ and propionic anhydride, providing moderate to good selectivity factors (S=12-37). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.01.018
• 作为产物：
  描述：

  3-(1-naphthyl)-2-propanone 在 哌啶 、 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 3-(naphthalen-1-yl)but-3-en-2-ol
  参考文献：
  名称：

  Nonenzymatic kinetic resolution of α-aryl substituted allylic alcohols catalyzed by acyl transfer catalyst Np-PIQ

  摘要：

  Chiral alpha-aryl substituted allylic alcohols are important versatile synthetic intermediates. We report here an effective nonenzymatic kinetic resolution of racemic alpha-aryl substituted allylic alcohols by introducing different aryl groups with acyl transfer catalyst Np-PIQ and propionic anhydride, providing moderate to good selectivity factors (S=12-37). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.01.018

文献信息

• Palladium-catalyzed arylation of unsymmetrical olefins. Bidentate phosphine ligand controlled regioselectivity
  作者：Walter Cabri、Ilaria Candiani、Angelo Bedeschi、Roberto Santi

  DOI：10.1021/jo00039a011

  日期：1992.6

  The palladium-catalyzed arylation of several unsymmetrical olefins by aryl triflates in the presence of bidentate phosphine ligands is described. The use of these ligands increases the influence that electronic factors have in determining regioselectivity of the reaction. The catalyst performances allow a revisiting of the scheme that describes the regioselectivity outcome in Heck-type reactions. Furthermore, a general mechanism for the palladium-catalyzed arylation of olefins is proposed.