(SS,S)-2-methylpropane-2-sulfinic acid [1-(tert-butyldimethylsilanyloxymethyl)-2-methylallyl]-amide | 926660-18-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (SS,S)-2-methylpropane-2-sulfinic acid [1-(tert-butyldimethylsilanyloxymethyl)-2-methylallyl]-amide
• 英文别名: (S_S,S)-2-methylpropane-2-sulfinic acid [1-(tert-butyldimethylsilanyloxymethyl)-2-methylallyl]-amide；N-[1-[(tert-butyldimethylsilyl)oxy]pent-4-en-2-yl]-2-methylpropane-2-sulfinamide；N-[(2S)-1-[(tert-butyldimethylsilyl)oxy]pent-4-en-2-yl]-2-methylpropane-2-sulfinamide
• CAS: 926660-18-6
• 化学式: C₁₅H₃₃NO₂SSi
• 分子量: 319.584
• InChiKey: CZMVTIXHFRHUBH-DJJJIMSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (SS,S)-2-methylpropane-2-sulfinic acid [1-(tert-butyldimethylsilanyloxymethyl)-2-methylallyl]-amide 在 盐酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 (S)-2-[4-(4-fluorophenyl)-imidazol-1-yl]-pent-4-en-1-ol
  参考文献：
  名称：

  Synthesis of Potent Bicyclic Bisarylimidazole c-Jun N-Terminal Kinase Inhibitors by Catalytic C−H Bond Activation

  摘要：

  The efficient preparation of the privileged bicyclic bisarylimidazole kinase inhibitor scaffold was accomplished using rhodium-catalyzed C-H activation and intramolecular alkylation. The key C-H activation/alkylation step represents one of the first evaluations of diastereocontrol in catalyzed C-H activation/olefin alkylation processes. Several inhibitors of JNK3 were prepared using this sequence, with the most potent inhibitor having an IC50 value of 1.6 nM.

  DOI：

  10.1021/ja0676004
• 作为产物：
  描述：

  叔丁基二甲基硅氧烷基乙醛 在 copper(II) sulfate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (SS,S)-2-methylpropane-2-sulfinic acid [1-(tert-butyldimethylsilanyloxymethyl)-2-methylallyl]-amide
  参考文献：
  名称：

  Synthesis of Potent Bicyclic Bisarylimidazole c-Jun N-Terminal Kinase Inhibitors by Catalytic C−H Bond Activation

  摘要：

  The efficient preparation of the privileged bicyclic bisarylimidazole kinase inhibitor scaffold was accomplished using rhodium-catalyzed C-H activation and intramolecular alkylation. The key C-H activation/alkylation step represents one of the first evaluations of diastereocontrol in catalyzed C-H activation/olefin alkylation processes. Several inhibitors of JNK3 were prepared using this sequence, with the most potent inhibitor having an IC50 value of 1.6 nM.

  DOI：

  10.1021/ja0676004

文献信息

• Synthesis of skeletally diverse alkaloid-like molecules: exploitation of metathesis substrates assembled from triplets of building blocks
  作者：Sushil K Maurya、Mark Dow、Stuart Warriner、Adam Nelson

  DOI：10.3762/bjoc.9.88

  日期：——

  A range of metathesis substrates was assembled from triplets of unsaturated building blocks. The approach involved the iterative attachment of a propagating and a terminating building block to a fluorous-tagged initiating building block. Metathesis cascade chemistry was used to "reprogram" the molecular scaffolds. Remarkably, in one case, a cyclopropanation reaction competed with the expected metathesis

  一系列复分解底物由三联体不饱和结构单元组装而成。该方法涉及将传播和终止构建块迭代连接到带有氟标记的起始构建块。复分解级联化学用于“重新编程”分子支架。值得注意的是，在一种情况下，环丙烷化反应与预期的复分解级联过程竞争。最后，证明复分解产物可以衍生以产生最终产物。在每个阶段，通过氟标记保护基团的存在促进纯化。
• Design, synthesis, and evaluation of novel ethambutol analogues
  作者：Raghunandan Yendapally、Richard E. Lee

  DOI：10.1016/j.bmcl.2008.01.065

  日期：2008.3

  Ethambutol is one of the front-line agents recommended by the World Health Organization for the treatment of tuberculosis. In an effort to develop more potent therapies to treat tuberculosis, novel unsymmetrical ethambutol analogues were successfully synthesized by a new route utilizing novel building blocks synthesized using Ellman's sulfinyl chemistry. The resulting analogues were tested for anti-tuberculosis activity yielding compounds with comparable anti-tuberculosis activity to ethambutol and increased lipophilicity that may instill better tissue penetration and serum half-life. (c) 2008 Elsevier Ltd. All rights reserved.