(4R,4'R,5R,5'R)-2,2'-(propane-2,2-diyl)bis(5-methyl-4,5-dihydrooxazole-4,2-diyl)bis(methylene)dimethanesulfonate | 1197419-81-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (4R,4'R,5R,5'R)-2,2'-(propane-2,2-diyl)bis(5-methyl-4,5-dihydrooxazole-4,2-diyl)bis(methylene)dimethanesulfonate
• CAS: 1197419-81-0
• 化学式: C₁₅H₂₆N₂O₈S₂
• 分子量: 426.512
• InChiKey: YMEUREVYMHPZLB-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  129.92
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (4R,4'R,5R,5'R)-2,2'-(propane-2,2-diyl)bis(5-methyl-4,5-dihydrooxazole-4,2-diyl)bis(methylene)dimethanesulfonate 、 4-羟基-二苯甲酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 48.5h， 以51%的产率得到(4R,4'R,5R,5'R)-BOX/BP
  参考文献：
  名称：

  带有 2-恶唑烷酮助剂的香豆素-3-甲酰胺与正丙基乙烯基醚和新戊酸乙烯酯分子间 [2+2] 的路易斯酸催化光环加成反应

  摘要：

  Intermolecular [2+2] photocycloaddition reactions between 3-(2-oxo-2H-chromene-3-carbonyl)oxazolidin-2-one with n-propyl vinyl ether and vinyl pivalate were carried out to give [2+2] cycloadducts in excellent yield with perfect regioselectivity. A Lewis acid catalyst (30 mol%) was moderately effective in accelerating the reaction. Furthermore, enantioselective reactions catalyzed by chiral Lewis acid catalysts (30 mol%) were performed to give cycloadducts in excellent yields with up to 13% ee.

  DOI：

  10.3987/com-18-s(t)44
• 作为产物：
  描述：

  甲基磺酰氯 、 (4R,4'R,5R,5'R)-2,2'-(propane-2,2-diyl)bis(5-methyl-4,5-dihydrooxazole-4,2-diyl)dimethanol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以76%的产率得到(4R,4'R,5R,5'R)-2,2'-(propane-2,2-diyl)bis(5-methyl-4,5-dihydrooxazole-4,2-diyl)bis(methylene)dimethanesulfonate
  参考文献：
  名称：

  Rational Design of Highly Effective Asymmetric Diels−Alder Catalysts Bearing 4,4′-Sulfonamidomethyl Groups

  摘要：

  The rational design of bis(oxazoline)-copper(II) catalysts based on postulated intramolecular secondary n-cation interaction for the highly enantioselective Diels-Alder reaction is presented. A theoretical calculation suggested that the n electrons of the 4,4'-sulfonamidomethyl groups successfully interact with the Cu(II) cation and that the counteranions with protons of sulfonamido groups. These secondary interactions might be essential for the high catalytic activity, the broad range of substrates, and the high level of induction of the enantioselectivity.

  DOI：

  10.1021/ja906098b
• 作为试剂：
  描述：

  环戊二烯 、 3-丙烯酰基-2-唑烷酮 在 (4R,4'R,5R,5'R)-2,2'-(propane-2,2-diyl)bis(5-methyl-4,5-dihydrooxazole-4,2-diyl)bis(methylene)dimethanesulfonate 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 降冰片烯缩醛3-((1S,2S,4S)-双环[2.2.1]庚-5-烯-2-羰基)恶唑烷-2-酮 、 3-[(1R,2R,4R)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]oxazolidin-2-one
  参考文献：
  名称：

  Rational Design of Highly Effective Asymmetric Diels−Alder Catalysts Bearing 4,4′-Sulfonamidomethyl Groups

  摘要：

  The rational design of bis(oxazoline)-copper(II) catalysts based on postulated intramolecular secondary n-cation interaction for the highly enantioselective Diels-Alder reaction is presented. A theoretical calculation suggested that the n electrons of the 4,4'-sulfonamidomethyl groups successfully interact with the Cu(II) cation and that the counteranions with protons of sulfonamido groups. These secondary interactions might be essential for the high catalytic activity, the broad range of substrates, and the high level of induction of the enantioselectivity.

  DOI：

  10.1021/ja906098b