1-bromo-5-(2-methyl-1,3-dioxolan-2-yl)pentan-2-one | 919787-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-5-(2-methyl-1,3-dioxolan-2-yl)pentan-2-one
• 英文别名: 1-Bromo-5-(2-methyl-1,3-dioxolan-2-yl)pentan-2-one
• CAS: 919787-98-7
• 化学式: C₉H₁₅BrO₃
• 分子量: 251.12
• InChiKey: UVFWRRJESIVBNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-bromo-5-(2-methyl-1,3-dioxolan-2-yl)pentan-2-one 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium methylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 42.0h， 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 、 氯化铵 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 1-bromo-5-(2-methyl-1,3-dioxolan-2-yl)pentan-2-one
  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

文献信息

• Stereoselective synthesis of rac-(8R,13S,14S)-7-oxa-estra-4,9-diene-3,17-dione
  作者：Fu-An Kang、Nareshkumar Jain、Zhihua Sui

  DOI：10.1016/j.tetlet.2006.10.098

  日期：2006.12

  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.