3-ethyl-4-isopropoxy-2,5,6-trimethylphenol | 869806-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-ethyl-4-isopropoxy-2,5,6-trimethylphenol
• 英文别名: 3-Ethyl-2,5,6-trimethyl-4-propan-2-yloxyphenol；3-ethyl-2,5,6-trimethyl-4-propan-2-yloxyphenol
• CAS: 869806-73-5
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: CXRIAAAUSHCJAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-ethyl-4-isopropoxy-2,5,6-trimethylphenol 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 5-Ethyl-2,3-dimethyl-6-methylidene-4-propan-2-yloxycyclohexa-2,4-dien-1-one 、 3-Ethyl-2,5-dimethyl-6-methylidene-4-propan-2-yloxycyclohexa-2,4-dien-1-one
  参考文献：
  名称：

  Synthesis and oxidation of ‘non-annulated’ vitamin E-like compounds

  摘要：

  Two model compounds (3 and 4) having the typical alpha-tocopherol -type substitution pattern of the aromatic ring, but lacking the annulated pyran ring, have been synthesized. Upon oxidation, the two possible ortho-quinone methides (oQMs) of each are formed in equal ratio. DFT calculations suggest that there is no angular strain in 3 and 4, and each of the oQM pairs is of similar energy. These results prove that the commonly observed regioselectivity in oxidations of vitamin E-type model compounds is not an electronic substitution effect, but a consequence of annulation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.009
• 作为产物：
  描述：

  5'-acetoxy-2'-hydroxy-3',4',6'-trimethylacetophenone 在 potassium carbonate 、 potassium iodide 、 锌 作用下， 以 盐酸 、 丙酮 为溶剂， 反应 26.0h， 生成 3-ethyl-4-isopropoxy-2,5,6-trimethylphenol
  参考文献：
  名称：

  Synthesis and oxidation of ‘non-annulated’ vitamin E-like compounds

  摘要：

  Two model compounds (3 and 4) having the typical alpha-tocopherol -type substitution pattern of the aromatic ring, but lacking the annulated pyran ring, have been synthesized. Upon oxidation, the two possible ortho-quinone methides (oQMs) of each are formed in equal ratio. DFT calculations suggest that there is no angular strain in 3 and 4, and each of the oQM pairs is of similar energy. These results prove that the commonly observed regioselectivity in oxidations of vitamin E-type model compounds is not an electronic substitution effect, but a consequence of annulation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.009

文献信息

• Synthesis and oxidation of ‘non-annulated’ vitamin E-like compounds
  作者：Thomas Rosenau、Amnon Stanger

  DOI：10.1016/j.tetlet.2005.09.009

  日期：2005.11

  Two model compounds (3 and 4) having the typical alpha-tocopherol -type substitution pattern of the aromatic ring, but lacking the annulated pyran ring, have been synthesized. Upon oxidation, the two possible ortho-quinone methides (oQMs) of each are formed in equal ratio. DFT calculations suggest that there is no angular strain in 3 and 4, and each of the oQM pairs is of similar energy. These results prove that the commonly observed regioselectivity in oxidations of vitamin E-type model compounds is not an electronic substitution effect, but a consequence of annulation. (c) 2005 Elsevier Ltd. All rights reserved.