benzooxepan-1-ol | 175229-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: benzooxepan-1-ol
• 英文别名: 1,3,4,5-tetrahydrobenzo[c]oxepin-1-ol；1,3,4,5-Tetrahydro-2-benzoxepin-1-ol
• CAS: 175229-25-1
• 化学式: C₁₀H₁₂O₂
• mdl: MFCD18450402
• 分子量: 164.204
• InChiKey: WVMCAFLEJYNSAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  benzooxepan-1-ol 以 氘代氯仿 为溶剂， 以97%的产率得到2-(3-Hydroxypropyl)benzaldehyde
  参考文献：
  名称：

  Neighboring Assistance of a Hydroxyl Group on Manganese Dioxide Oxidation of Benzyl Alcohols to Lactones

  摘要：

  o-Hydroxymethylbenzyl alcohol and o-hydroxyethylbenzyl alcohols have been converted to phthalide and dihydroisocoumarins, very easily and in high yields, by oxidation with non-activated manganese dioxide. In contrast, the reaction of o-hydroxypropylbenzyl alcohol stopped at the aldehyde level, and afforded only a small amount of the corresponding lactone under the same condition. This implies that the first oxidation product, a benzaldehyde, could be oxidized further via a hemiacetal, but the second oxidation to lactone is very much dependent on the ability of stable intramolecular hemiacetal formation, and not on the intermolecular mode at all.

  DOI：

  10.3987/com-95-s48
• 作为产物：
  描述：

  3-[2-(羟基甲基)苯基]-1-丙醇 在 Oxone 、 2-iodo-3,4,5,6-tetramethylbenzoic acid 作用下， 以 水 、 乙腈 为溶剂， 反应 8.0h， 以65%的产率得到benzooxepan-1-ol
  参考文献：
  名称：

  Facile organocatalytic domino oxidation of diols to lactones by in situ-generated TetMe-IBX

  摘要：

  The domino oxidation of diols to lactones is an important transformation, and catalytic protocols that allow this conversion smoothly are scarce. Capitalizing on the established reactivity of tetramethyl-IBX (TetMe-IBX) and its in situ generation in the presence of a co-oxidant, such as oxone, we have shown that a variety of diols can be converted to the corresponding lactones in respectable yields by employing the precursor of TetMe-IBX, namely, tetramethyl-o-iodobenzoic acid (TetMe-IA), as a catalyst in 5 mol % in the presence of 2 equiv of oxone. (c) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.01.034

文献信息

• Neighboring Assistance of a Hydroxyl Group on Manganese Dioxide Oxidation of Benzyl Alcohols to Lactones
  作者：Katsuya Endo、Hiroyasu Takahashi、Minako Aihara

  DOI：10.3987/com-95-s48

  日期：——

  o-Hydroxymethylbenzyl alcohol and o-hydroxyethylbenzyl alcohols have been converted to phthalide and dihydroisocoumarins, very easily and in high yields, by oxidation with non-activated manganese dioxide. In contrast, the reaction of o-hydroxypropylbenzyl alcohol stopped at the aldehyde level, and afforded only a small amount of the corresponding lactone under the same condition. This implies that the first oxidation product, a benzaldehyde, could be oxidized further via a hemiacetal, but the second oxidation to lactone is very much dependent on the ability of stable intramolecular hemiacetal formation, and not on the intermolecular mode at all.
• Facile organocatalytic domino oxidation of diols to lactones by in situ-generated TetMe-IBX
  作者：Samik Jhulki、Saona Seth、Manas Mondal、Jarugu Narasimha Moorthy

  DOI：10.1016/j.tet.2014.01.034

  日期：2014.4

  The domino oxidation of diols to lactones is an important transformation, and catalytic protocols that allow this conversion smoothly are scarce. Capitalizing on the established reactivity of tetramethyl-IBX (TetMe-IBX) and its in situ generation in the presence of a co-oxidant, such as oxone, we have shown that a variety of diols can be converted to the corresponding lactones in respectable yields by employing the precursor of TetMe-IBX, namely, tetramethyl-o-iodobenzoic acid (TetMe-IA), as a catalyst in 5 mol % in the presence of 2 equiv of oxone. (c) 2014 Published by Elsevier Ltd.