7a-methyl-4-[5-(2-methyl-1,3-dioxolan-2-yl)-2-oxopentyloxy]-2,3,7,7a-tetrahydro-6H-indene-1,5-dione | 919787-99-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7a-methyl-4-[5-(2-methyl-1,3-dioxolan-2-yl)-2-oxopentyloxy]-2,3,7,7a-tetrahydro-6H-indene-1,5-dione
• 英文别名: 7a-Methyl-4-[5-(2-methyl-1,3-dioxolan-2-yl)-2-oxopentoxy]-2,3,6,7-tetrahydroindene-1,5-dione
• CAS: 919787-99-8
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: MDMLEPPEOQXULQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7a-methyl-4-[5-(2-methyl-1,3-dioxolan-2-yl)-2-oxopentyloxy]-2,3,7,7a-tetrahydro-6H-indene-1,5-dione 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 、 甲苯 为溶剂， 反应 25.0h， 生成 3a-Methyl-6-(3-oxo-butyl)-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione
  参考文献：
  名称：

  Stereoselective synthesis of rac-(8R,13S,14S)-7-oxa-estra-4,9-diene-3,17-dione

  摘要：

  The first synthesis of a novel oxa-steroid, rac-(8R,13S,14S)-7-oxa-estra-4,9-diene-3,17-dione has been achieved via stereoselective catalytic hydrogenation of the tetra-substituted indene intermediate, whose structure was confirmed by X-ray crystallography. In contrast to the previous reports of similar indene systems, it was found that catalytic hydrogenation of indenes with a large substituent at the C-2 position and a bulky beta-oriented protective group at the C-6 position resulted in cis-indanes instead of trans-indanes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.098
• 作为产物：
  描述：

  5-(2-methyl-1,3-dioxolan-2-yl)-2-pentanone 在 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 、 potassium carbonate 、 氯化铵 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 7a-methyl-4-[5-(2-methyl-1,3-dioxolan-2-yl)-2-oxopentyloxy]-2,3,7,7a-tetrahydro-6H-indene-1,5-dione
  参考文献：
  名称：

  Stereoselective synthesis of rac-(8R,13S,14S)-7-oxa-estra-4,9-diene-3,17-dione

  摘要：

  The first synthesis of a novel oxa-steroid, rac-(8R,13S,14S)-7-oxa-estra-4,9-diene-3,17-dione has been achieved via stereoselective catalytic hydrogenation of the tetra-substituted indene intermediate, whose structure was confirmed by X-ray crystallography. In contrast to the previous reports of similar indene systems, it was found that catalytic hydrogenation of indenes with a large substituent at the C-2 position and a bulky beta-oriented protective group at the C-6 position resulted in cis-indanes instead of trans-indanes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.098