acetic acid 2-(4-chloro-phenyl)-2-hydroxy-propyl ester | 171417-10-0

• 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: acetic acid 2-(4-chloro-phenyl)-2-hydroxy-propyl ester
• 英文别名: 2-(4-chlorophenyl)-2-hydroxypropyl acetate；[2-(4-Chlorophenyl)-2-hydroxypropyl] acetate
• CAS: 171417-10-0
• 化学式: C₁₁H₁₃ClO₃
• 分子量: 228.675
• InChiKey: BDLKQUBOQPEQEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氯甲基苯乙烯 、 溶剂黄146 在 [Pd(dppp)(H₂O)2]⁽²⁺⁾*2(OTf)^(1-) 碘苯二乙酸 、 水 作用下， 反应 1.5h， 以70%的产率得到acetic acid 2-(4-chloro-phenyl)-2-hydroxy-propyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Olefin Dioxygenation

  摘要：

  A general method for the vicinal dioxygenation of olefins was developed using cationic Pd diphosphine complexes as the catalysts and Phl(OAC)(2) as the terminal oxidant. In comparison to known Pd-catalyzed vicinal oxidations, this method is suitable for a broad range of olefins in both inter- and intramolecular reactions. An (18)O-labeling experiment provides insight into the mechanism of this transformation which presumably involves Pd(II)/Pd(IV) intermediates.

  DOI：

  10.1021/ja711029u

文献信息

• Synthesis of β-acetoxy alcohols by PhI(OAc)₂-mediated metal-free diastereoselective β-acetoxylation of alcohols
  作者：Chun-Yang Zhao、Liang-Gui Li、Qing-Rong Liu、Cheng-Xue Pan、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1039/c6ob01203e

  日期：——

  β-Acetoxy alcohols can be synthesized in good yields with excellent diastereoselectivity from tertiary alcohols through PhI(OAc)2-mediated metal-free β-acetoxylation. Mechanistic studies showed that the β-acetoxylation process might undergo dehydration and sequential highly regioselective and diastereoseletive dioxygenation. Gram scale and diverse useful scaffolds could be prepared via this β-acetoxylation

  β-乙酰氧基醇可以通过PhI（OAc）2介导的无金属β-乙酰氧基化反应从叔醇中以良好的非对映选择性高收率合成。机理研究表明，β-乙酰氧基化过程可能会发生脱水，继而发生高度区域选择性和非对映异构的双加氧反应。可以通过该β-乙酰氧基化方法制备革兰氏规模和各种有用的支架。