N-(benzothiophenesulfone-2-methyl)piperidine | 109893-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(benzothiophenesulfone-2-methyl)piperidine
• 英文别名: 2-(Piperidin-1-ylmethyl)-1-benzothiophene 1,1-dioxide
• CAS: 109893-20-1
• 化学式: C₁₄H₁₇NO₂S
• 分子量: 263.36
• InChiKey: WNSTYCZZJDBNKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-苯并噻吩-2-甲醇 在 sodium perborate 作用下， 以 四氢呋喃 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-(benzothiophenesulfone-2-methyl)piperidine
  参考文献：
  名称：

  The 1,1-Dioxobenzo[b]thiophene-2-ylmethyloxycarbonyl (Bsmoc) Amino-Protecting Group

  摘要：

  Full details are presented for use of the Bsmoc amino-protecting group for both solid phase and rapid continuous solution syntheses. Application to the latter methodology represents a significant improvement over the corresponding Fmoc-based method for rapid solution synthesis due to the opportunity to use water or saturated sodium-chloride solution rather than an acidic phosphate buffer to remove all byproducts, with consequent cleaner phase separation and higher yields of the growing peptide. Comparison of the Bsmoc and Bspoc functions showed that the former, because of steric hindrance, does not suffer from the competitive or premature deblocking observed with the Bspoc system. Because of its incorporation of a styrene chromophore, resin loading of Bsmoc amino acids could be followed as has previously been shown for the Fmoc analogues. Applications of Bsmoc chemistry to peptide sequences incorporating the base sensitive Asp-Gly unit gave less contamination due to aminosuccinimide formation than comparable syntheses involving standard Fmoc chemistry because a weaker or less concentrated base could be used in the deblocking step. Experimental details are presented for building up peptides in solution via the continuous methodology. Deblockings involved the use of insoluble piperazino silica as well as the polyamine TAEA which simplified aqueous separation of the growing, but nonisolated peptide product, from excess acylating agent and other side products formed in the deblocking process. By the appropriate choice of base, one can act selectively at either site of a molecule which incorporates both beta-elimination and Michael acceptor sites as protective units (Bsmoc vs Fm and Fmoc vs Bsm).

  DOI：

  10.1021/jo982140l

文献信息

• The Bsmoc group as a novel scaffold for the design of irreversible inhibitors of cysteine proteases
  作者：Jim Iley、Rui Moreira、Luísa Martins、Rita C. Guedes、Cláudio M. Soares

  DOI：10.1016/j.bmcl.2006.02.007

  日期：2006.5

  not significantly affected by the nature of the carboxylic or carbamic acid leaving group. These Michael acceptors are irreversible inhibitors of the cysteine proteases papain and human liver cathepsin B, displaying first-order kinetics with respect to inhibitor concentration. In contrast, none of the Bsmoc derivatives inhibited porcine pancreatic elastase, a serine protease.

  1,1-二氧代苯并[b]噻吩-2-基甲氧基羰基（Bsmoc）支架的氨基甲酸酯和酯衍生物可以通过迈克尔加成反应与巯基反应，其反应速率不受羧基或氨基甲酸离去基团性质的明显影响。这些迈克尔受体是半胱氨酸蛋白酶木瓜蛋白酶和人肝组织蛋白酶B的不可逆抑制剂，在抑制剂浓度方面表现出一级动力学。相反，没有Bsmoc衍生物抑制猪胰弹性蛋白酶，一种丝氨酸蛋白酶。
• New Family of Base- and Nucleophile-Sensitive Amino-Protecting Groups. A Michael-Acceptor-Based Deblocking Process. Practical Utilization of the 1,1-Dioxobenzo[<i>b</i>]thiophene-2-ylmethyloxycarbonyl (Bsmoc) Group
  作者：Louis A. Carpino、Michael Philbin、Mohamed Ismail、George A. Truran、E. M. E. Mansour、Shin Iguchi、Dumitru Ionescu、Ayman El-Faham、Christoph Riemer、Ralf Warrass、Manfred S. Weiss

  DOI：10.1021/ja9713690

  日期：1997.10.1