2-(2-chloro-3-methoxyphenyl)-1,3-dioxolane | 1309612-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-chloro-3-methoxyphenyl)-1,3-dioxolane
• CAS: 1309612-52-9
• 化学式: C₁₀H₁₁ClO₃
• 分子量: 214.649
• InChiKey: JCRRPRZQEPWYFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-chloro-3-methoxyphenyl)-1,3-dioxolane 、 1-萘硼酸 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 10,16-Dimethyl-13-[2-[2,3,4,5,6-pentakis(4-methylphenyl)phenyl]phenyl]-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene 、 cesium fluoride 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以63%的产率得到C₂₀H₁₈O₃
  参考文献：
  名称：

  Asymmetric Suzuki–Miyaura cross-coupling of aryl chlorides with enhancement of reaction time and catalyst turnover

  摘要：

  A series of new chiral phosphonite ligands were evaluated for the palladium-catalyzed asymmetric Suzuki-Miyaura cross-coupling reactions of aryl chlorides. Ligand 4 gave 91% yield and 78% ee with 0.5 mol % catalyst loading for the coupling of aryl boronic acid and aryl chloride in 5 h. When the catalyst loading was lowered to 0.1 mol % the same reaction gave 75% yield and 76% ee. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.051
• 作为产物：
  描述：

  乙二醇 、 2-氯-3-甲氧基苯甲醛 在 对甲苯磺酸 作用下， 反应 16.0h， 以77%的产率得到2-(2-chloro-3-methoxyphenyl)-1,3-dioxolane
  参考文献：
  名称：

  Asymmetric Suzuki–Miyaura cross-coupling of aryl chlorides with enhancement of reaction time and catalyst turnover

  摘要：

  A series of new chiral phosphonite ligands were evaluated for the palladium-catalyzed asymmetric Suzuki-Miyaura cross-coupling reactions of aryl chlorides. Ligand 4 gave 91% yield and 78% ee with 0.5 mol % catalyst loading for the coupling of aryl boronic acid and aryl chloride in 5 h. When the catalyst loading was lowered to 0.1 mol % the same reaction gave 75% yield and 76% ee. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.051

文献信息

• Asymmetric Suzuki–Miyaura cross-coupling of aryl chlorides with enhancement of reaction time and catalyst turnover
  作者：Toshinori Kamei、Akihiro H. Sato、Tetsuo Iwasawa

  DOI：10.1016/j.tetlet.2011.03.051

  日期：2011.5

  A series of new chiral phosphonite ligands were evaluated for the palladium-catalyzed asymmetric Suzuki-Miyaura cross-coupling reactions of aryl chlorides. Ligand 4 gave 91% yield and 78% ee with 0.5 mol % catalyst loading for the coupling of aryl boronic acid and aryl chloride in 5 h. When the catalyst loading was lowered to 0.1 mol % the same reaction gave 75% yield and 76% ee. (C) 2011 Elsevier Ltd. All rights reserved.