3-(o-tolyl)propane-1,2-diol | 17131-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(o-tolyl)propane-1,2-diol
• 英文别名: 1-(o-Tolyl)-propan-2,3-diol；3-o-Tolyl-propandiol-(1.2)；3-o-Tolyl-1,2-propandiol；markiertes-3--propandiol-(1,2)；3-o-Tolyl-propan-1,2-diol；3-(2-Methylphenyl)propane-1,2-diol；3-(2-methylphenyl)propane-1,2-diol
• CAS: 17131-15-6
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: WUKRLARDMBGRIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(嘧啶-5-基)苯甲醛 、 3-(o-tolyl)propane-1,2-diol 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以81%的产率得到5-(2-(4-(2-methylbenzyl)-1,3-dioxolan-2-yl)phenyl)pyrimidine
  参考文献：
  名称：

  Palladium-Catalyzed meta-C–H Olefination of Arene-Tethered Diols Directed by Well-Designed Pyrimidine-Based Group

  摘要：

  The palladium-catalyzed meta-olefination of arene-tethered diols attached to a well-designed pyrimidine moiety is presented. Applications of the protocol are illustrated by the synthesis of various diol-based natural products, such as coumarins, phenylpropanoids, stilbenes, and chalcones. Advantages of this method are demonstrated through the easy removal of the template and a gram-scale olefination reaction. Finally, experimental verification, including H-1 NMR, ESI-MS and IR, and DFT studies are undertaken to elucidate the mechanistic complexity.

  DOI：

  10.1021/acs.orglett.9b00433
• 作为产物：
  描述：

  1-烯丙基-2-甲苯 在 甲基磺酰胺 、 AD-mix β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 6.0h， 以45%的产率得到3-(o-tolyl)propane-1,2-diol
  参考文献：
  名称：

  Palladium-Catalyzed meta-C–H Olefination of Arene-Tethered Diols Directed by Well-Designed Pyrimidine-Based Group

  摘要：

  The palladium-catalyzed meta-olefination of arene-tethered diols attached to a well-designed pyrimidine moiety is presented. Applications of the protocol are illustrated by the synthesis of various diol-based natural products, such as coumarins, phenylpropanoids, stilbenes, and chalcones. Advantages of this method are demonstrated through the easy removal of the template and a gram-scale olefination reaction. Finally, experimental verification, including H-1 NMR, ESI-MS and IR, and DFT studies are undertaken to elucidate the mechanistic complexity.

  DOI：

  10.1021/acs.orglett.9b00433

文献信息

• Beasley et al., Journal of Pharmacy and Pharmacology, 1959, vol. 11, p. 36,41
  作者：Beasley et al.

  DOI：——

  日期：——
• Palladium-Catalyzed <i>meta</i>-C–H Olefination of Arene-Tethered Diols Directed by Well-Designed Pyrimidine-Based Group
  作者：Siqiang Fang、Xiaobing Wang、Fucheng Yin、Pei Cai、Huali Yang、Lingyi Kong

  DOI：10.1021/acs.orglett.9b00433

  日期：2019.3.15

  The palladium-catalyzed meta-olefination of arene-tethered diols attached to a well-designed pyrimidine moiety is presented. Applications of the protocol are illustrated by the synthesis of various diol-based natural products, such as coumarins, phenylpropanoids, stilbenes, and chalcones. Advantages of this method are demonstrated through the easy removal of the template and a gram-scale olefination reaction. Finally, experimental verification, including H-1 NMR, ESI-MS and IR, and DFT studies are undertaken to elucidate the mechanistic complexity.