3-acetyl-2-hydroxy-2-phenylpropyl acetate | 95971-76-9

• 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-acetyl-2-hydroxy-2-phenylpropyl acetate
• CAS: 95971-76-9
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: HLZAGJCYPPDAHB-UHFFFAOYSA-N

物化性质

• 沸点：
  150-160 °C(Press: 10 Torr)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (+/-)-1-acetoxy-2-phenyl-2-propanol 在 sodium perborate 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 生成 3-acetyl-2-hydroxy-2-phenylpropyl acetate
  参考文献：
  名称：

  A Convenient Synthesis of 2-Phenylglycerol

  摘要：

  1,3-Dihydroxyacetone dimer is treated with trimethylsilyl chloride and triethylamine in dichloromethane to provide monomeric ketone having both of its alcohols protected as their di-TMS ethers. The latter is added to phenylmagnesium bromide in ether at -78 degrees C. Work-up by treatment with aqueous ammonium chloride followed by 2 N HCl provides 2-phenylglycerol in 70% yield.

  DOI：

  10.1080/00397910008087018

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。
• Kotani,Eiichi; Kobayashi, Shigeki; Ishii, Yoko, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 11, p. 4281 - 4291
  作者：Kotani,Eiichi、Kobayashi, Shigeki、Ishii, Yoko、Tobinaga, Seisho

  DOI：——

  日期：——