4-(1,1-Dimethyl-propyl)-1-(2,2,2-trifluoro-ethoxy)-isochroman-3-yl-hydroperoxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-(1,1-Dimethyl-propyl)-1-(2,2,2-trifluoro-ethoxy)-isochroman-3-yl-hydroperoxide
• 英文别名: 3-hydroperoxy-4-(2-methylbutan-2-yl)-1-(2,2,2-trifluoroethoxy)-3,4-dihydro-1H-isochromene
• 化学式: C₁₆H₂₁F₃O₄
• 分子量: 334.336
• InChiKey: XDINLWJIYHHFNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(1,1-Dimethyl-propyl)-1-(2,2,2-trifluoro-ethoxy)-isochroman-3-yl-hydroperoxide 在 吡啶 、 异氰酸苯酯 作用下， 以 苯 为溶剂， 反应 15.0h， 以36%的产率得到4-(1,1-Dimethyl-propyl)-1-(2,2,2-trifluoro-ethoxy)-isochroman-3-one
  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
• 作为产物：
  描述：

  2,2,2-三氟乙醇 、 1-t-Pentylindene 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到4-(1,1-Dimethyl-propyl)-1-(2,2,2-trifluoro-ethoxy)-isochroman-3-yl-hydroperoxide
  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

• 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.