2-methyl-propane-2-sulfonic acid [(S)-2-methyl-1-(5-methyl-2-piperazin-1-yl-phenyl)-propyl]-amide

• 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: 2-methyl-propane-2-sulfonic acid [(S)-2-methyl-1-(5-methyl-2-piperazin-1-yl-phenyl)-propyl]-amide
• 英文别名: 2-methyl-N-[(1S)-2-methyl-1-(5-methyl-2-piperazin-1-ylphenyl)propyl]propane-2-sulfonamide
• 化学式: C₁₉H₃₃N₃O₂S
• 分子量: 367.556
• InChiKey: GQKBYZFFVOYACM-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  69.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 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 、 三氟乙酸 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 18.5h， 生成 2-methyl-propane-2-sulfonic acid [(S)-2-methyl-1-(5-methyl-2-piperazin-1-yl-phenyl)-propyl]-amide
  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

文献信息

• Practical Asymmetric Synthesis of α-Branched 2-Piperazinylbenzylamines by 1,2-Additions of Organometallic Reagents to <i>N</i>-<i>tert</i>-Butanesulfinyl Imines
  作者：Wanlong Jiang、Chen、Dragan Marinkovic、Joe A. Tran、Caroline W. Chen、L. Melissa Arellano、Nicole S. White、Fabio C. Tucci

  DOI：10.1021/jo051514p

  日期：2005.10.1

  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.