(R)-2-methyl-N-[(1-methyl-1H-pyrazol-4-yl)methylidene]-2-propanesulfinamide | 1000407-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (R)-2-methyl-N-[(1-methyl-1H-pyrazol-4-yl)methylidene]-2-propanesulfinamide
• 英文别名: Rs-2-methyl-propane-2-sulfinic acid 1-methyl-1H-pyrazol-4-yl-methyleneamide；(R,E)-2-methyl-N-((1-methyl-1H-pyrazol-4-yl)methylene)propane-2-sulfinamide；(R)-2-methyl-N-[(1-methylpyrazol-4-yl)methylidene]propane-2-sulfinamide
• CAS: 1000407-77-1
• 化学式: C₉H₁₅N₃OS
• 分子量: 213.304
• InChiKey: UOISCRINJGHLGV-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-methyl-N-[(1-methyl-1H-pyrazol-4-yl)methylidene]-2-propanesulfinamide 在 盐酸 、 锌 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Diastereoselective In and Zn-mediated allylation of pyrazol-4-yl derived (R)-tert-butanesulfinyl imines: synthesis of enantiomerically pure 6-(pyrazol-4-yl)-piperidin-2,4-diones

  摘要：

  The In and Zn-mediated allylation of substituted pyrazol-4-yl derived (R)-N-tert-butanesulfinyl imines proceeds with high diastereoselectivity depending on the conditions and additives (up to 99.4% de). Thus, the synthesized diastereomeric homoallylsulfinamides were isolated and characterized as pure diastereomers, which were then converted into the corresponding pyrazol-4-yl-derived N-Boc-homoallylamines via consecutive treatment with HCl and Boc(2)O. The latter were then subjected to a sequence of reactions: cyclobromocarbamation with NBS and enolateisocyanate rearrangement with tBuOK to give novel enantiomerically pure (S)-6-(pyrazol-4-yl)-piperidine-2,4-diones in 88-96% yield. The absolute configurations of the allylation products were assigned by X-ray single crystal analysis of the intermediate bromomethylurethanes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.03.003
• 作为产物：
  描述：

  1-甲基-1H-吡唑-4-甲醛 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) isopropylate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以97%的产率得到(R)-2-methyl-N-[(1-methyl-1H-pyrazol-4-yl)methylidene]-2-propanesulfinamide
  参考文献：
  名称：

  Diastereoselective In and Zn-mediated allylation of pyrazol-4-yl derived (R)-tert-butanesulfinyl imines: synthesis of enantiomerically pure 6-(pyrazol-4-yl)-piperidin-2,4-diones

  摘要：

  The In and Zn-mediated allylation of substituted pyrazol-4-yl derived (R)-N-tert-butanesulfinyl imines proceeds with high diastereoselectivity depending on the conditions and additives (up to 99.4% de). Thus, the synthesized diastereomeric homoallylsulfinamides were isolated and characterized as pure diastereomers, which were then converted into the corresponding pyrazol-4-yl-derived N-Boc-homoallylamines via consecutive treatment with HCl and Boc(2)O. The latter were then subjected to a sequence of reactions: cyclobromocarbamation with NBS and enolateisocyanate rearrangement with tBuOK to give novel enantiomerically pure (S)-6-(pyrazol-4-yl)-piperidine-2,4-diones in 88-96% yield. The absolute configurations of the allylation products were assigned by X-ray single crystal analysis of the intermediate bromomethylurethanes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.03.003

文献信息

• SERINE/THREONINE KINASE INHIBITORS
  申请人：Blake Jim

  公开号：US20140066453A1

  公开（公告）日：2014-03-06

  Compounds having the formula I wherein R 2 , X and Z as defined herein are inhibitors of ERK kinase. Also disclosed are compositions and methods for treating hyperproliferative disorders.

  具有公式I的化合物，其中R2、X和Z如本文所定义，是ERK激酶的抑制剂。还披露了用于治疗过度增殖性疾病的组合物和方法。
• WO2008/834
  申请人：——

  公开号：——

  公开（公告）日：——
• SERINE/THREONINE KINASE INHIBITORS FOR THE TREATMENT OF HYPERPROLIFERATIVE DISEASES
  申请人：Array Biopharma, Inc.

  公开号：EP2888247B1

  公开（公告）日：2020-03-25
• US9388171B2
  申请人：——

  公开号：US9388171B2

  公开（公告）日：2016-07-12
• Diastereoselective In and Zn-mediated allylation of pyrazol-4-yl derived (R)-tert-butanesulfinyl imines: synthesis of enantiomerically pure 6-(pyrazol-4-yl)-piperidin-2,4-diones
  作者：Nikolai Yu. Kuznetsov、Victor N. Khrustalev、Tatyana V. Strelkova、Yuri N. Bubnov

  DOI：10.1016/j.tetasy.2014.03.003

  日期：2014.4

  The In and Zn-mediated allylation of substituted pyrazol-4-yl derived (R)-N-tert-butanesulfinyl imines proceeds with high diastereoselectivity depending on the conditions and additives (up to 99.4% de). Thus, the synthesized diastereomeric homoallylsulfinamides were isolated and characterized as pure diastereomers, which were then converted into the corresponding pyrazol-4-yl-derived N-Boc-homoallylamines via consecutive treatment with HCl and Boc(2)O. The latter were then subjected to a sequence of reactions: cyclobromocarbamation with NBS and enolateisocyanate rearrangement with tBuOK to give novel enantiomerically pure (S)-6-(pyrazol-4-yl)-piperidine-2,4-diones in 88-96% yield. The absolute configurations of the allylation products were assigned by X-ray single crystal analysis of the intermediate bromomethylurethanes. (C) 2014 Elsevier Ltd. All rights reserved.