(S_S,S) 2-methylpropane-2-sulfinic acid [1-(tert-butyldimethylsilanyloxymethyl)-allyl]-amide | 926660-07-3

• 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: (S_S,S) 2-methylpropane-2-sulfinic acid [1-(tert-butyldimethylsilanyloxymethyl)-allyl]-amide
• 英文别名: (S)-N-((S)-1-((tert-Butyldimethylsilyl)oxy)but-3-en-2-yl)-2-methylpropane-2-sulfinamide；(S)-N-[(2S)-1-[tert-butyl(dimethyl)silyl]oxybut-3-en-2-yl]-2-methylpropane-2-sulfinamide
• CAS: 926660-07-3
• 化学式: C₁₄H₃₁NO₂SSi
• 分子量: 305.557
• InChiKey: LYWXLNZTROQRSS-SGTLLEGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S_S,S) 2-methylpropane-2-sulfinic acid [1-(tert-butyldimethylsilanyloxymethyl)-allyl]-amide 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 (S)-1-(tert-butyldimethylsilyloxy)but-3-en-2-amine
  参考文献：
  名称：

  环状氨基酸合成中的立体控制：通过氢键定向氢化的新配体。

  摘要：

  描述了一种用于氮杂环的直接加氢的系统，其中氢通过具有简单膦配体的铑催化剂顺式递送至羟甲基。该化学方法被用于合成林可霉素的羟基酸部分和阿加曲班的胡椒酸部分。一系列对照实验表明，立体选择性是配位和氢键结合的结果。

  DOI：

  10.1039/c9ob00003h
• 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 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (S_S,S) 2-methylpropane-2-sulfinic acid [1-(tert-butyldimethylsilanyloxymethyl)-allyl]-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

• Stereocontrol in the synthesis of cyclic amino acids: a new ligand for directed hydrogenation through hydrogen bonding
  作者：Vasudeva Rao Gandi、Bao Nguyen Do Doan、Sivarajan Kasinathan、Roderick W. Bates

  DOI：10.1039/c9ob00003h

  日期：——

  for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chemistry is applied to the synthesis of the hygric acid moiety of lincomycin and the pipecolic acid moiety of Argatroban. A series of control experiments indicate that the stereoselectivity is a result of a combination

  描述了一种用于氮杂环的直接加氢的系统，其中氢通过具有简单膦配体的铑催化剂顺式递送至羟甲基。该化学方法被用于合成林可霉素的羟基酸部分和阿加曲班的胡椒酸部分。一系列对照实验表明，立体选择性是配位和氢键结合的结果。
• Synthesis of Potent Bicyclic Bisarylimidazole c-Jun N-Terminal Kinase Inhibitors by Catalytic C−H Bond Activation
  作者：Jason C. Rech、Michihisa Yato、Derek Duckett、Brian Ember、Philip V. LoGrasso、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ja0676004

  日期：2007.1.1

  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.