4α,4aα,6β,8aβ-Octahydro-1,1,6-trimethyl-3-oxo-1H-2-benzopyran-4-carboxylic acid methyl ester

• 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: 4α,4aα,6β,8aβ-Octahydro-1,1,6-trimethyl-3-oxo-1H-2-benzopyran-4-carboxylic acid methyl ester
• 英文别名: (4R,4aR,6R,8aR)-4-methoxycarbonyl-1,1,6-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-2,3-benzopyrone；methyl (4R,4aR,6R,8aR)-1,1,6-trimethyl-3-oxo-4a,5,6,7,8,8a-hexahydro-4H-isochromene-4-carboxylate
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: OEAUBIXFHFHULA-GWOFURMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 (+)-香茅醛 在 ethylenediamine Tetraacetic Acid 、 盐酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 57.0h， 生成 4α,4aα,6β,8aβ-Octahydro-1,1,6-trimethyl-3-oxo-1H-2-benzopyran-4-carboxylic acid methyl ester
  参考文献：
  名称：

  DIASTEROSELECTIVE FORMATION OF a-METHOXYCARBONYL LACTONES THROUGH AN INTRAMOLECULAR DIELS–ALDER REACTION: (4RS,4aRS,6RS,8aRS)-, (4S,4aS,6S,8aS)- AND (4R,4aR,6R,8aR)-4-METHOXYCARBONYL-1,1,6-TRIMETHYL-1,4,4A,5,6,7,8,8a-OCTAHYDRO-2,3-BENZOPYRONE [rac-5, (+)-5, AND (−)-5]

  摘要：

  DOI：

  10.15227/orgsyn.069.0031

文献信息

• Surface-Mediated Reactions. 6. Effects of Silica Gel and Alumina on Acid-Catalyzed Reactions
  作者：Paul J. Kropp、Gary W. Breton、Stephen L. Craig、Scott D. Crawford、William F. Durland、John E. Jones、J. Scott Raleigh

  DOI：10.1021/jo00118a035

  日期：1995.6

  Adsorption of a variety of acids to chromatographic silica gel results in substantial enhancement of their catalytic activity-affording easily prepared, environmentally benign heterogeneous acids that are highly effective in mediating a number of processes. This was shown for the isomerization of allene 1 and dimerization of the corresponding 1,3-diene 2; cyclization of (R)-citronellal (5), the related diester 10, and 1,5-cyclooctadiene (15); Rupe rearrangement of alkynol 18; and Friedel-Crafts cyclodehydration of alcohols 21. By contrast, commercially available Nafion-H was significantly less effective as a heterogeneous acid catalyst. Chromatographic alumina displayed enigmatic behavior, showing enhanced acidity on the adsorption of HCl but little or no acidity on the adsorption of a variety of other types of acid. The results are discussed in terms of the surface structures of silica gel and alumina.
• DIASTEROSELECTIVE FORMATION OF a-METHOXYCARBONYL LACTONES THROUGH AN INTRAMOLECULAR DIELS–ALDER REACTION: (4RS,4aRS,6RS,8aRS)-, (4S,4aS,6S,8aS)- AND (4R,4aR,6R,8aR)-4-METHOXYCARBONYL-1,1,6-TRIMETHYL-1,4,4A,5,6,7,8,8a-OCTAHYDRO-2,3-BENZOPYRONE [rac-5, (+)-5, AND (−)-5]
  作者：Tietze、Kiedrowski、Fahlbusch、Voss

  DOI：10.15227/orgsyn.069.0031

  日期：——