[(4R,5R,9R)-9-(2,2-dimethylpropanoylamino)spiro[4.4]nonan-4-yl] 2-cyclopropylideneacetate | 1001329-88-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(4R,5R,9R)-9-(2,2-dimethylpropanoylamino)spiro[4.4]nonan-4-yl] 2-cyclopropylideneacetate
• CAS: 1001329-88-9
• 化学式: C₁₉H₂₉NO₃
• 分子量: 319.444
• InChiKey: BHPHQGKEOJXDEB-SPYBWZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(4R,5R,9R)-9-(2,2-dimethylpropanoylamino)spiro[4.4]nonan-4-yl] 2-cyclopropylideneacetate 生成 N-((1R,5S)-spiro[4.4]non-6-en-1-yl)pivalamide
  参考文献：
  名称：

  Diastereoselective Diels−Alder Reactions of a Novel Cyclopropenyl-Containing Chiral Auxiliary

  摘要：

  A novel cyclopropenyl-containing 1,3-spiroaminoalcohol auxiliary has been used in a variety of asymmetric Diels-Alder reactions providing endo adducts with diastereomeric ratios ranging from 2:1 up to >99:1. In addition, unexpected regiochemistry was observed for a Diels-Alder reaction between cyclopropenyl dienophile and 4-vinyl-1,2-dihydronapthalene.

  DOI：

  10.1021/ol702280q
• 作为产物：
  描述：

  2-环亚丙基乙酸 、 (1R,5R,6R)-6-(2,2-dimethylpropanamido)-spiro[4.4]-nonan-1-ol 在 三甲基乙酰氯 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以78%的产率得到[(4R,5R,9R)-9-(2,2-dimethylpropanoylamino)spiro[4.4]nonan-4-yl] 2-cyclopropylideneacetate
  参考文献：
  名称：

  Diastereoselective Diels−Alder Reactions of a Novel Cyclopropenyl-Containing Chiral Auxiliary

  摘要：

  A novel cyclopropenyl-containing 1,3-spiroaminoalcohol auxiliary has been used in a variety of asymmetric Diels-Alder reactions providing endo adducts with diastereomeric ratios ranging from 2:1 up to >99:1. In addition, unexpected regiochemistry was observed for a Diels-Alder reaction between cyclopropenyl dienophile and 4-vinyl-1,2-dihydronapthalene.

  DOI：

  10.1021/ol702280q

文献信息

• Diastereoselective Diels−Alder Reactions of a Novel Cyclopropenyl-Containing Chiral Auxiliary
  作者：Jeff R. Henderson、Masood Parvez、Brian A. Keay

  DOI：10.1021/ol702280q

  日期：2007.12.1

  A novel cyclopropenyl-containing 1,3-spiroaminoalcohol auxiliary has been used in a variety of asymmetric Diels-Alder reactions providing endo adducts with diastereomeric ratios ranging from 2:1 up to >99:1. In addition, unexpected regiochemistry was observed for a Diels-Alder reaction between cyclopropenyl dienophile and 4-vinyl-1,2-dihydronapthalene.