5,5-bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)nonane-1,9-diol | 1374295-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5,5-bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)nonane-1,9-diol
• 英文别名: 5,5-bis[(3aS,8bR)-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-2-yl]nonane-1,9-diol
• CAS: 1374295-26-7
• 化学式: C₂₉H₃₄N₂O₄
• 分子量: 474.6
• InChiKey: LCXJCSNMNHYZDX-QEGGNFSNSA-N

物化性质

• 沸点：
  654.8±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5-bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)nonane-1,9-diol 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以55%的产率得到5,5-bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)nonane-1,9-ditosylate
  参考文献：
  名称：

  Recyclable copper catalysts based on ionic-tagged C2-symmetric Indabox ligands and their application in asymmetric Henry reactions

  摘要：

  New imidazolium/pyrrolidinium-tagged Indabox ligands were designed and prepared. Catalysts based on these ligands with Cu(OAc)(2)center dot H2O were applied to the asymmetric Henry reaction using various aldehydes and CH3NO2, the products were obtained in high enantioselectivity. Specifically, (R)-1-(2-methoxylphenyl)-2-nitroethanol was obtained in 94% ee in MeOH. Furthermore, the catalyst based on 7 could be recycled at least 12 times by simple wash without an obvious loss of activity or enantioselectivity. This catalytic procedure demonstrated the potential for catalyst recyclability in the asymmetric Henry reaction. Additionally, a theoretical mechanistic study was conducted to explain the origin of the enantioselectivity. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2012.02.044
• 作为产物：
  描述：

  (+)-2,2'-亚甲基双[(3aR,8aS)-3a,8a-二氢-8H-茚苯[1,2-d]并恶唑 在 四丁基氟化铵 、 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 5,5-bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)nonane-1,9-diol
  参考文献：
  名称：

  Recyclable copper catalysts based on ionic-tagged C2-symmetric Indabox ligands and their application in asymmetric Henry reactions

  摘要：

  New imidazolium/pyrrolidinium-tagged Indabox ligands were designed and prepared. Catalysts based on these ligands with Cu(OAc)(2)center dot H2O were applied to the asymmetric Henry reaction using various aldehydes and CH3NO2, the products were obtained in high enantioselectivity. Specifically, (R)-1-(2-methoxylphenyl)-2-nitroethanol was obtained in 94% ee in MeOH. Furthermore, the catalyst based on 7 could be recycled at least 12 times by simple wash without an obvious loss of activity or enantioselectivity. This catalytic procedure demonstrated the potential for catalyst recyclability in the asymmetric Henry reaction. Additionally, a theoretical mechanistic study was conducted to explain the origin of the enantioselectivity. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2012.02.044