| 1542164-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• CAS: 1542164-59-9
• 化学式: C₁₆H₂₂N₂
• 分子量: 242.364
• InChiKey: VMEZGHMRYLTNJC-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  15.27
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  、 苯甲醛 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以75%的产率得到(1S,2R)-1'-benzyl-1-(pyrrolidin-1-yl)-1,3-dihydrospiro[indene-2,2'-pyrrolidine]
  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：

  2-溴溴苄 在 10 wt% Pd(OH)2 on carbon 、 盐酸羟胺 、 氢气 、 叔丁基锂 、 sodium carbonate 、 三氟乙酸 、 sodium iodide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 118.0h， 生成
  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