1-acetoxy-4,4-diisopropyl-2-methyl-tetrahydrofuran | 243983-00-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: 1-acetoxy-4,4-diisopropyl-2-methyl-tetrahydrofuran
• 英文别名: [3-methyl-5,5-di(propan-2-yl)oxolan-2-yl] acetate
• CAS: 243983-00-8
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: POQXLTPKEFTMCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-甲基-1-(三甲基硅氧基)-1-丙烯 、 1-acetoxy-4,4-diisopropyl-2-methyl-tetrahydrofuran 在 溴化锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以80%的产率得到2-methyl-2-[(2S,3S)-3-methyl-5,5-di(propan-2-yl)oxolan-2-yl]propanal
  参考文献：
  名称：

  Divergent diastereoselectivity in the addition of nucleophiles to tetrahydrofuran-derived oxonium ions

  摘要：

  Alkyl substituted lactol acetates have been found to undergo highly stereoselective substitution reactions mediated by tin (IV) bromide. The highest selectivity is observed in the case of 4,4-di-isopropyl, 2-methyl substitution in which the selectivity depends on the nucleophile. Allyltrimethylsilane adds with high (95:5) 1,2-syn selectivity while 2-methyl-trimethylsiloxy propene adds with high (>98:2) anti selectivity. These results can be rationalized through conformational analysis of the oxonium ion intermediate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00441-x
• 作为产物：
  描述：

  2,5-二甲基-3-(1-甲基乙基)-5-己烯-3-醇 在 硼烷四氢呋喃络合物 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 1-acetoxy-4,4-diisopropyl-2-methyl-tetrahydrofuran
  参考文献：
  名称：

  Divergent diastereoselectivity in the addition of nucleophiles to tetrahydrofuran-derived oxonium ions

  摘要：

  Alkyl substituted lactol acetates have been found to undergo highly stereoselective substitution reactions mediated by tin (IV) bromide. The highest selectivity is observed in the case of 4,4-di-isopropyl, 2-methyl substitution in which the selectivity depends on the nucleophile. Allyltrimethylsilane adds with high (95:5) 1,2-syn selectivity while 2-methyl-trimethylsiloxy propene adds with high (>98:2) anti selectivity. These results can be rationalized through conformational analysis of the oxonium ion intermediate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00441-x

文献信息

• Divergent diastereoselectivity in the addition of nucleophiles to tetrahydrofuran-derived oxonium ions
  作者：Jared T Shaw、K.A Woerpel

  DOI：10.1016/s0040-4020(99)00441-x

  日期：1999.7

  Alkyl substituted lactol acetates have been found to undergo highly stereoselective substitution reactions mediated by tin (IV) bromide. The highest selectivity is observed in the case of 4,4-di-isopropyl, 2-methyl substitution in which the selectivity depends on the nucleophile. Allyltrimethylsilane adds with high (95:5) 1,2-syn selectivity while 2-methyl-trimethylsiloxy propene adds with high (>98:2) anti selectivity. These results can be rationalized through conformational analysis of the oxonium ion intermediate. (C) 1999 Elsevier Science Ltd. All rights reserved.