N-((1S,2R)-1'-(2,3,4,5,6-pentamethylbenzyl)-1,3-dihydrospiro[indene-2,2'-pyrrolidin]-1-yl)acetamide | 1542164-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: N-((1S,2R)-1'-(2,3,4,5,6-pentamethylbenzyl)-1,3-dihydrospiro[indene-2,2'-pyrrolidin]-1-yl)acetamide
• CAS: 1542164-79-3
• 化学式: C₂₆H₃₄N₂O
• 分子量: 390.569
• InChiKey: MITUTUSCNNLGST-IZZNHLLZSA-N

物化性质

• 沸点：
  589.4±39.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.34
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-((1S,2R)-1'-(2,3,4,5,6-pentamethylbenzyl)-1,3-dihydrospiro[indene-2,2'-pyrrolidin]-1-yl)acetamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到(1S,2R)-N-ethyl-1'-(2,3,4,5,6-pentamethylbenzyl)-1,3-dihydrospiro[indene-2,2'-pyrrolidin]-1-amine
  参考文献：
  名称：

  Synthesis of Tunable Diamine Ligands with Spiro Indane-2,2′-pyrrolidine Backbone and Their Applications in Enantioselective Henry Reaction

  摘要：

  Novel diamine ligands with spiro indane-2,2'-pyrrolidine scaffold were synthesized starting from Seebach's oxazolidinone 6 and were subsequently employed in asymmetric Henry reaction. Following the initial experimental findings, further synthesis resulted in two types of spiro diamines, with varying substituents at both nitrogen atoms. Ligands of type A, containing a small substituent at N-1' atom, and a large group at N-1 atom gave predominantly the S-configured beta-nitroalcohol, while ligands of type B, with the reversed location of small and large substituents furnished the R-configured product. Both types of ligands turned out to be versatile catalysts for the Henry reaction between nitromethane and an assortment of aryl as well as alkyl aldehydes offering either S- (lig. A) or R-configured (lig. B) nitroalcohols in a good to high chemical yield and an excellent enantioselectivity up to 99% ee.

  DOI：

  10.1021/jo402631u
• 作为产物：
  描述：

  tert-butyl (1S,2R)-1-acetamido-1,3-dihydrospiro[indene-2,2'-pyrrolidine]-1'-carboxylate 在 sodium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 3.5h， 生成 N-((1S,2R)-1'-(2,3,4,5,6-pentamethylbenzyl)-1,3-dihydrospiro[indene-2,2'-pyrrolidin]-1-yl)acetamide
  参考文献：
  名称：

  Synthesis of Tunable Diamine Ligands with Spiro Indane-2,2′-pyrrolidine Backbone and Their Applications in Enantioselective Henry Reaction

  摘要：

  Novel diamine ligands with spiro indane-2,2'-pyrrolidine scaffold were synthesized starting from Seebach's oxazolidinone 6 and were subsequently employed in asymmetric Henry reaction. Following the initial experimental findings, further synthesis resulted in two types of spiro diamines, with varying substituents at both nitrogen atoms. Ligands of type A, containing a small substituent at N-1' atom, and a large group at N-1 atom gave predominantly the S-configured beta-nitroalcohol, while ligands of type B, with the reversed location of small and large substituents furnished the R-configured product. Both types of ligands turned out to be versatile catalysts for the Henry reaction between nitromethane and an assortment of aryl as well as alkyl aldehydes offering either S- (lig. A) or R-configured (lig. B) nitroalcohols in a good to high chemical yield and an excellent enantioselectivity up to 99% ee.

  DOI：

  10.1021/jo402631u