3,5-diisopropyl-1-acetoxybenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3,5-diisopropyl-1-acetoxybenzene
• 英文别名: 5-acetoxy-1,3-diisopropylbenzene；Phenol, 3,5-bis(1-methylethyl)-, acetate；[3,5-di(propan-2-yl)phenyl] acetate
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: IANMANYZPNUMKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三異丙苯 、 乙酸酐 在 N-羟基邻苯二甲酰亚胺 、 偶氮二异丁腈 、 氧气 、 硫酸 、 吡啶 作用下， 以 乙腈 为溶剂， 20.0~120.0 ℃ 、101.32 kPa 条件下， 反应 6.0h， 以52%的产率得到3,5-diisopropyl-1-acetoxybenzene
  参考文献：
  名称：

  Aerobic oxidation of 1,3,5-triisopropylbenzene using N-hydroxyphthalimide (NHPI) as key catalyst

  摘要：

  The first systematic study on the aerobic oxidation of 1,3,5-triisopropylbenzene was examined by the use of N-hydroxyphthalimide (NHPI) as a key catalyst. It was found that 1,3,5-triisopropylbenzene was efficiently oxidized with 02 in the presence of a catalytic amount of NHPI and azobisisobutyronitrile (AIBN) at 75 degrees C. Upon treatment of the resulting products with sulfuric acid followed by acetic anhydride led to 5-acetoxy-1,3-diisopropyl benzene and 3,5-diacetoxy-1-isopropyl benzene as major products and a small amount of 1,3,5-triacetoxybenzene. When t-butyl peroxypivalate (BPP) was employed as a radical initiator, the oxidation could be achieved in good yield even at 50 degrees C. This oxidation provides a facile method for preparing phenol derivatives bearing an isopropyl moiety, which can be used as pharmaceutical starting materials. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.087

文献信息

• US4164510A
  申请人：——

  公开号：US4164510A

  公开（公告）日：1979-08-14
• US4200763A
  申请人：——

  公开号：US4200763A

  公开（公告）日：1980-04-29
• US4202833A
  申请人：——

  公开号：US4202833A

  公开（公告）日：1980-05-13
• Aerobic oxidation of 1,3,5-triisopropylbenzene using N-hydroxyphthalimide (NHPI) as key catalyst
  作者：Yasuhiro Aoki、Naruhisa Hirai、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1016/j.tet.2005.08.087

  日期：2005.11

  The first systematic study on the aerobic oxidation of 1,3,5-triisopropylbenzene was examined by the use of N-hydroxyphthalimide (NHPI) as a key catalyst. It was found that 1,3,5-triisopropylbenzene was efficiently oxidized with 02 in the presence of a catalytic amount of NHPI and azobisisobutyronitrile (AIBN) at 75 degrees C. Upon treatment of the resulting products with sulfuric acid followed by acetic anhydride led to 5-acetoxy-1,3-diisopropyl benzene and 3,5-diacetoxy-1-isopropyl benzene as major products and a small amount of 1,3,5-triacetoxybenzene. When t-butyl peroxypivalate (BPP) was employed as a radical initiator, the oxidation could be achieved in good yield even at 50 degrees C. This oxidation provides a facile method for preparing phenol derivatives bearing an isopropyl moiety, which can be used as pharmaceutical starting materials. (c) 2005 Elsevier Ltd. All rights reserved.