4-{4-methyl-2-[(S)-2-methyl-1-(2-methyl-propane-2-sulfonylamino)-propyl]-phenyl}-piperazine-1-carboxylic aicd tert-butyl ester | 869478-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-{4-methyl-2-[(S)-2-methyl-1-(2-methyl-propane-2-sulfonylamino)-propyl]-phenyl}-piperazine-1-carboxylic aicd tert-butyl ester
• 英文别名: tert-butyl 4-[2-[(1S)-1-(tert-butylsulfonylamino)-2-methylpropyl]-4-methylphenyl]piperazine-1-carboxylate
• CAS: 869478-60-4
• 化学式: C₂₄H₄₁N₃O₄S
• 分子量: 467.673
• InChiKey: UOJOPCMBCRAOHF-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  87.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-{4-methyl-2-[(S)-2-methyl-1-(2-methyl-propane-2-sulfonylamino)-propyl]-phenyl}-piperazine-1-carboxylic aicd tert-butyl ester 在 三氟甲磺酸 、 苯甲醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到4-[2-((S)-1-amino-2-methyl-propyl)-4-methyl-phenyl]-piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Practical Asymmetric Synthesis of α-Branched 2-Piperazinylbenzylamines by 1,2-Additions of Organometallic Reagents to N-tert-Butanesulfinyl Imines

  摘要：

  2-[4-(tert-Butoxycarbonyl)piperazinyl]benzylidene-tert-butanesulfinamides underwent nucleophilic 1,2-addition with different organometallic reagents to give highly diastereomerically enriched adducts. X-ray crystallography of the resulting alpha-branched N-Boc-2-piperazinylbenzyl-tert-butanesulfinamides confirms different mechanisms depending on the organometallic reagent used. Differential deprotection of the N-Boc and the tert-butanesulfinamides was investigated, and the dehydration byproducts have been identified and characterized. To avoid the formation of byproducts in the acidic deprotection step, the N-tert-butanesulfinamide group was converted to the corresponding N-tert-butanesulfonamide (Bus), which allowed for clean orthogonal deprotection. The efficient synthesis and deprotection of the N-Boc-2-piperazinylbenzyl-tert-butanesulfinamides herein described constitutes an attractive method for extensive structure-activity studies in the search for novel ligands of the human melanocortin 4 receptor.

  DOI：

  10.1021/jo051514p
• 作为产物：
  描述：

  4-(2-formyl-4-methyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester 在 titanium(IV) tetraethanolate 、 三甲基铝 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 正庚烷 、 二氯甲烷 、 正戊烷 为溶剂， 反应 17.75h， 生成 4-{4-methyl-2-[(S)-2-methyl-1-(2-methyl-propane-2-sulfonylamino)-propyl]-phenyl}-piperazine-1-carboxylic aicd tert-butyl ester
  参考文献：
  名称：

  Practical Asymmetric Synthesis of α-Branched 2-Piperazinylbenzylamines by 1,2-Additions of Organometallic Reagents to N-tert-Butanesulfinyl Imines

  摘要：

  2-[4-(tert-Butoxycarbonyl)piperazinyl]benzylidene-tert-butanesulfinamides underwent nucleophilic 1,2-addition with different organometallic reagents to give highly diastereomerically enriched adducts. X-ray crystallography of the resulting alpha-branched N-Boc-2-piperazinylbenzyl-tert-butanesulfinamides confirms different mechanisms depending on the organometallic reagent used. Differential deprotection of the N-Boc and the tert-butanesulfinamides was investigated, and the dehydration byproducts have been identified and characterized. To avoid the formation of byproducts in the acidic deprotection step, the N-tert-butanesulfinamide group was converted to the corresponding N-tert-butanesulfonamide (Bus), which allowed for clean orthogonal deprotection. The efficient synthesis and deprotection of the N-Boc-2-piperazinylbenzyl-tert-butanesulfinamides herein described constitutes an attractive method for extensive structure-activity studies in the search for novel ligands of the human melanocortin 4 receptor.

  DOI：

  10.1021/jo051514p