4-{2-[(R)-3-methyl-1-((R_S)-2-methyl-propane-2-sulfinylamino)-butyl]-6-trifluoromethyl-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

• 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-{2-[(R)-3-methyl-1-((R_S)-2-methyl-propane-2-sulfinylamino)-butyl]-6-trifluoromethyl-phenyl}-piperazine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 4-[2-[(1R)-1-[[(R)-tert-butylsulfinyl]amino]-3-methylbutyl]-6-(trifluoromethyl)phenyl]piperazine-1-carboxylate
• 化学式: C₂₅H₄₀F₃N₃O₃S
• 分子量: 519.672
• InChiKey: RVOJWIUZYTWUOP-OTASCSKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-{2-[((R_S)-2-methyl-propane-2-sulfinylimino)-methyl]-6-trifluoromethyl-phenyl}-piperazine-1-carboxylic acid tert-butyl ester 、 (2-methylpropyl)lithium 在 三甲基铝 作用下， 以 四氢呋喃 、 正己烷 、 正庚烷 为溶剂， 反应 1.0h， 以90%的产率得到4-{2-[(R)-3-methyl-1-((R_S)-2-methyl-propane-2-sulfinylamino)-butyl]-6-trifluoromethyl-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

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.