1-Methoxy-4-hydroxy-4,5-dihydro-1H-2,3-benzodioxepin

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1-Methoxy-4-hydroxy-4,5-dihydro-1H-2,3-benzodioxepin
• 英文别名: 1-methoxy-4,5-dihydro-1H-2,3-benzodioxepin-4-ol
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: SGCKRCCUGGOJEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Methoxy-4-hydroxy-4,5-dihydro-1H-2,3-benzodioxepin 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 以71%的产率得到2-(2-甲氧羰基苯基)乙酸
  参考文献：
  名称：

  New approaches to the synthesis of spiro-peroxylactones

  摘要：

  三氟乙醇中（烯丙二氧）环十二烷过氧化氢的臭氧分解反应得到了相应α-过氧化氢和α-羟基取代的螺-四氧杂环烷混合物，其环大小范围为7至12。过氧化氢的脱水或羟基化合物的氧化反应生成了相应的过氧化环酸。1,2,6,7-四氧杂螺[7.11]十九烷-3-酮的固态结构通过X射线晶体学分析确定。

  DOI：

  10.1039/b300342f
• 作为产物：
  描述：

  甲醇 、 茚 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到1-Methoxy-4-hydroxy-4,5-dihydro-1H-2,3-benzodioxepin
  参考文献：
  名称：

  Ozonolyses of Indene and of 1-Alkyl- and 1,1-Dialkyl-Substituted Indenes in Protic Solvents. Remarkable Effects of the Substituent Steric Bulk and the Solvent Nucleophilicity on the Direction of Cleavage of the Primary Ozonides and on the Mode of Capture of the Carbonyl Oxide Intermediates by the Solvents

  摘要：

  Ozonolyses of indene (1a) and of 1-alkyl- and 1,1-dialkyl-substituted indenes 1b-h in protic solvents including methanol, 2-propanol, and trifluoroethanol revealed that (i) two types of the solvent-derived products, a hemiperacetal and/or an isochroman derivative, are produced depending on the nucleophilicity of the solvent and the steric bulk of the alkyl substituent(s), and (ii) the regiochemistry of the fragmentation of a primary ozonide is a marked function of the nature of the 1-alkyl-substituent. In the case ofindene (1a) and 1-substituted indenes 1b-e, both possible modes of primary ozonide cleavage operate competitively yielding two carbonyl oxide intermediates in roughly equal amounts, whereas in the case of 1,1-dialkyl-substituted indenes 1f-h the contribution of the less-hindered carbonyl oxide predominates.

  DOI：

  10.1021/jo00120a018

文献信息

• New approaches to the synthesis of spiro-peroxylactones
  作者：Kevin J. McCullough、Hidekazu Tokuhara、Araki Masuyama、Masatomo Nojima

  DOI：10.1039/b300342f

  日期：2003.4.23

  Ozonolysis of (alkenyldioxy)cyclododecyl hydroperoxides in trifluoroethanol gave a separable mixture of the corresponding α-hydroperoxy- and α-hydroxy-substituted spiro-tetraoxacycloalkanes with ring sizes in the range 7–12. Dehydration of the hydroperoxides or oxidation of the hydroxy-compounds afforded the corresponding peroxylactones. The solid-state structure of 1,2,6,7-tetraoxaspiro[7.11]nonadecan-3-one was determined by X-ray crystallographic analysis.

  三氟乙醇中（烯丙二氧）环十二烷过氧化氢的臭氧分解反应得到了相应α-过氧化氢和α-羟基取代的螺-四氧杂环烷混合物，其环大小范围为7至12。过氧化氢的脱水或羟基化合物的氧化反应生成了相应的过氧化环酸。1,2,6,7-四氧杂螺[7.11]十九烷-3-酮的固态结构通过X射线晶体学分析确定。
• Ozonolyses of Indene and of 1-Alkyl- and 1,1-Dialkyl-Substituted Indenes in Protic Solvents. Remarkable Effects of the Substituent Steric Bulk and the Solvent Nucleophilicity on the Direction of Cleavage of the Primary Ozonides and on the Mode of Capture of the Carbonyl Oxide Intermediates by the Solvents
  作者：Koichi Teshima、Shin-ichi Kawamura、Yoshihiro Ushigoe、Masatomo Nojima、Kevin J. McCullough

  DOI：10.1021/jo00120a018

  日期：1995.7

  Ozonolyses of indene (1a) and of 1-alkyl- and 1,1-dialkyl-substituted indenes 1b-h in protic solvents including methanol, 2-propanol, and trifluoroethanol revealed that (i) two types of the solvent-derived products, a hemiperacetal and/or an isochroman derivative, are produced depending on the nucleophilicity of the solvent and the steric bulk of the alkyl substituent(s), and (ii) the regiochemistry of the fragmentation of a primary ozonide is a marked function of the nature of the 1-alkyl-substituent. In the case ofindene (1a) and 1-substituted indenes 1b-e, both possible modes of primary ozonide cleavage operate competitively yielding two carbonyl oxide intermediates in roughly equal amounts, whereas in the case of 1,1-dialkyl-substituted indenes 1f-h the contribution of the less-hindered carbonyl oxide predominates.