tert-butyl 2-[(1R)-5-(2,6-dimethylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate | 1414782-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: tert-butyl 2-[(1R)-5-(2,6-dimethylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate
• CAS: 1414782-33-4
• 化学式: C₂₇H₃₆N₄O₂
• 分子量: 448.608
• InChiKey: RSHKUVPBQOQIFA-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 4-(chloromethyl)-4-formylpiperidine-1-carboxylate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 66.0h， 生成 tert-butyl 2-[(1R)-5-(2,6-dimethylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate
  参考文献：
  名称：

  Spiroazetidine–piperidine bromoindane as a key modular template to access a variety of compounds via C–C and C–N bond-forming reactions

  摘要：

  In the context of our ghrelin inverse agonist program, a functionalized bromoindane 3 provided a versatile intermediate for structure-activity relationship studies. After developing operationally simple cross-coupling reactions, a broad spectrum of chemical space was successfully explored. Optimization of a one-pot borylation/Suzuki sequence provided the desired products in high yield with low loading of the palladium catalyst. High yields of N-linked heterocyclic analogues were obtained through palladium catalyzed C-N bond formation. In addition, carboxylation of the bromoindane provided an indane carboxylic acid for further diversification. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.047

文献信息

• Spiroazetidine–piperidine bromoindane as a key modular template to access a variety of compounds via C–C and C–N bond-forming reactions
  作者：Dilinie P. Fernando、Wenhua Jiao、Jana Polivkova、Jun Xiao、Steven B. Coffey、Colin Rose、Allyn Londregan、James Saenz、Ramsay Beveridge、Yingxin Zhang、Gregory E. Storer、Derek Vrieze、Noe Erasga、Ryan Jones、Vishal Khot、Kimberly O. Cameron、Kim F. McClure、Samit K. Bhattacharya、Suvi T.M. Orr

  DOI：10.1016/j.tetlet.2012.09.047

  日期：2012.11

  In the context of our ghrelin inverse agonist program, a functionalized bromoindane 3 provided a versatile intermediate for structure-activity relationship studies. After developing operationally simple cross-coupling reactions, a broad spectrum of chemical space was successfully explored. Optimization of a one-pot borylation/Suzuki sequence provided the desired products in high yield with low loading of the palladium catalyst. High yields of N-linked heterocyclic analogues were obtained through palladium catalyzed C-N bond formation. In addition, carboxylation of the bromoindane provided an indane carboxylic acid for further diversification. (C) 2012 Elsevier Ltd. All rights reserved.