(1S,2S)-methyl-(2-pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester | 475495-76-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1S,2S)-methyl-(2-pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester
• CAS: 475495-76-2
• 化学式: C₂₀H₃₀N₂O₂
• 分子量: 330.47
• InChiKey: CIGNNOCWAIPXFD-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  32.78
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-methyl-(2-pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以95%的产率得到(1S,2S)-methyl-(2-pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-amin
  参考文献：
  名称：

  An Expedient Enantioselective Route to Diaminotetralins:  Application in the Preparation of Analgesic Compounds

  摘要：

  [GRAPHICS]Advances to the rhodium-catalyzed asymmetric ring-opening protocol have allowed this methodology to be extended to azabicyclic alkenes, the first time that rhodium has been used in allylic functionalizations with nitrogen leaving groups. The product diaminotetralins are important medicinal compounds. The synthetic utility of this methodology has been demonstrated in the total synthesis of an analgesic compound where the tetralin core, the regiochemistry, and the relative and absolute stereochemistry are all established in the ring-opening step.

  DOI：

  10.1021/ol026579i
• 作为产物：
  描述：

  (1S,2S)-(2-pyrrolidin-1-yl-1,2-dihydro-naphthalen-1-yl)-carbamic acid tert-butyl ester 在 sodium periodate 、 potassium hydride 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成 (1S,2S)-methyl-(2-pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  An Expedient Enantioselective Route to Diaminotetralins:  Application in the Preparation of Analgesic Compounds

  摘要：

  [GRAPHICS]Advances to the rhodium-catalyzed asymmetric ring-opening protocol have allowed this methodology to be extended to azabicyclic alkenes, the first time that rhodium has been used in allylic functionalizations with nitrogen leaving groups. The product diaminotetralins are important medicinal compounds. The synthetic utility of this methodology has been demonstrated in the total synthesis of an analgesic compound where the tetralin core, the regiochemistry, and the relative and absolute stereochemistry are all established in the ring-opening step.

  DOI：

  10.1021/ol026579i