(1R)-3-methylene-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid (1R,5R,6R)-6-(2,2-dimethyl-propionylamino)-spiro[4.4]non-1-yl ester | 1206817-51-7

• 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: (1R)-3-methylene-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid (1R,5R,6R)-6-(2,2-dimethyl-propionylamino)-spiro[4.4]non-1-yl ester
• 英文别名: [(4R,5R,9R)-9-(2,2-dimethylpropanoylamino)spiro[4.4]nonan-4-yl] (1R,2S,4S)-3-methylidenebicyclo[2.2.2]oct-5-ene-2-carboxylate
• CAS: 1206817-51-7
• 化学式: C₂₄H₃₅NO₃
• 分子量: 385.547
• InChiKey: VTNFWVVMZXXQGN-ULBRBPAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,5R,6R)-buta-2,3-dienoic acid 6-(2,2-dimethyl-propionylamino)-spiro[4.4]non-1-yl ester 、 1,3-环己二烯 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 以58%的产率得到(1R)-3-methylene-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid (1R,5R,6R)-6-(2,2-dimethyl-propionylamino)-spiro[4.4]non-1-yl ester
  参考文献：
  名称：

  Diastereoselective Diels−Alder Reactions with an Allenyl-Containing Spiro-Amido Chiral Auxiliary

  摘要：

  A novel allenyl-containing 1,3-spiro-amido alcohol auxiliary has been prepared and used in a variety of diastereo-selective Diels-Alder reactions providing exclusively endo adducts with diastereomeric ratios ranging from 2:1 to > 99:1.

  DOI：

  10.1021/jo902556b

文献信息

• Diastereoselective Diels−Alder Reactions with an Allenyl-Containing Spiro-Amido Chiral Auxiliary
  作者：Jeff R. Henderson、Julian P. Chesterman、Masood Parvez、Brian A. Keay

  DOI：10.1021/jo902556b

  日期：2010.2.5

  A novel allenyl-containing 1,3-spiro-amido alcohol auxiliary has been prepared and used in a variety of diastereo-selective Diels-Alder reactions providing exclusively endo adducts with diastereomeric ratios ranging from 2:1 to > 99:1.