(R)-2-methyl-butane-2-sulfinamide | 446021-71-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: (R)-2-methyl-butane-2-sulfinamide
• 英文别名: (R)-2-Methylbutane-2-sulfinamide
• CAS: 446021-71-2
• 化学式: C₅H₁₃NOS
• 分子量: 135.23
• InChiKey: XMGHCOUHHPRMOH-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氯苯甲醛 、 (R)-2-methyl-butane-2-sulfinamide 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到2-Methyl-butane-2-sulfinic acid 1-(4-chloro-phenyl)-meth-(E)-ylideneamide
  参考文献：
  名称：

  有效调节芳烃和链亚磺酰胺以高度对映选择性合成（S）-4-氯苯基苯基甲胺，这是抗组氨酸（S）-西替利嗪的关键中间体

  摘要：

  在（S）-西替利嗪关键中间体的合成中，向新的和受阻位的三异丙基苯亚磺酰胺（TIPBSA）衍生的氯苯基亚胺的苯基MgBr加成过程中，已实现了高非对映选择性（> 94％）。出乎意料的是，在相同的反应条件下，甲苯磺酰胺衍生的氯苯基亚胺仅提供10％的ee。

  DOI：

  10.1016/s0040-4039(03)00903-1
• 作为产物：
  描述：

  magnesium,2-methylbutane,chloride 在 氨 、 lithium 、 ferric nitrate 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 (R)-2-methyl-butane-2-sulfinamide
  参考文献：
  名称：

  Asymmetric Synthesis of Sulfinamides Using (−)-Quinine as Chiral Auxiliary

  摘要：

  A process has been designed and demonstrated for the asymmetric synthesis of sulfinamides using quinine as auxiliary. A variety of chiral sulfinamides including N-alkyl sulfinamides with diverse structure were prepared in good yields and excellent enantioselectivity starting from easily available and inexpensive reagents. The auxiliary quinine could be recovered and recycled.

  DOI：

  10.1021/jo201825b

文献信息

• Design and Synthesis of Chiral Oxathiozinone Scaffolds: Efficient Synthesis of Hindered Enantiopure Sulfinamides and Sulfinyl Ketimines
  作者：Zhengxu S. Han、Melissa A. Herbage、Hari P. R. Mangunuru、Yibo Xu、Li Zhang、Jonathan T. Reeves、Joshua D. Sieber、Zhibin Li、Philomen DeCroos、Yongda Zhang、Guisheng Li、Ning Li、Shengli Ma、Nelu Grinberg、Xiaojun Wang、Navneet Goyal、Dhileep Krishnamurthy、Bruce Lu、Jinhua J. Song、Guijun Wang、Chris H. Senanayake

  DOI：10.1002/anie.201301676

  日期：2013.6.24

  Is that SO? The title scaffolds have a highly active and properly differentiated SO bond for the efficient synthesis of enantiopure sulfinamides. The method is practical, green, and has the potential to provide an economical commercial process for the synthesis of bulky sulfinamides.

  那是SO吗？标题支架具有高活性和适当区分的SO键，可有效合成对映纯的亚磺酰胺。该方法是实用的，绿色的，并且有潜力为合成庞大的亚磺酰胺提供经济的商业方法。
• Diastereoselective Synthesis of Chiral Oxathiazine 2‐Oxide Scaffolds as Sulfinyl Transfer Agents
  作者：Arianna Quintavalla、Ruben Veronesi、Demetra Zambardino、Davide Carboni、Marco Lombardo

  DOI：10.1002/adsc.202200113

  日期：2022.5.17

  An efficient diastereoselective route for the preparation of chiral oxathiazine 2-oxide scaffolds as sulfinyl transfer agents, using tert-butanesulfinamide (tBSA) both as the source of chirality and as the precursor to the required nitrogen electron withdrawing group on the scaffold, was developed. This methodology allows the introduction of different substituents on the chiral scaffold, using commercially

  使用叔丁烷亚磺酰胺（tBSA) 作为手性来源和支架上所需的氮吸电子基团的前体被开发出来。该方法允许使用市售试剂和标准合成转化在手性支架上引入不同的取代基。合成的支架在对映体富集的亚磺酰胺的制备中进行了测试，提供了与文献中迄今为止提出的亚磺酰基转移剂相当的结果，并打开了进一步阐述这些支架的可能性，目的是在固相上支持它们以促进它们的回收和再利用。
• First Application of Tunable Alkyl or Aryl Sulfinamides to the Stereoselective Synthesis of a Chiral Amine:  Asymmetric Synthesis of (<i>R</i>)-Didesmethylsibutramine ((<i>R</i>)-DDMS) Using (<i>R)</i>-Triethylmethylsulfinamide ((<i>R</i>)-TESA)
  作者：Zhengxu Han、Dhileepkumar Krishnamurthy、Derek Pflum、Paul Grover、Stephen A. Wald、Chris H. Senanayake

  DOI：10.1021/ol026699q

  日期：2002.11.1

  A highly diastereoselective addition of i-BuLi to a triethylmethylsulfinamide derived aldimine was used as the key step in the first asymmetric synthesis of (R)-didesmethylsibutramine, a metabolite of sibutramine for the potential treatment of CNS disorders. [reaction: see text]

  将i-BuLi高度非对映选择性地添加到三乙基甲基亚磺酰胺衍生的Aldimine中，作为（R）-didesmethylsibutramine的首个不对称合成的关键步骤。[反应：看文字]
• Properly Designed Modular Asymmetric Synthesis for Enantiopure Sulfinamide Auxiliaries from <i>N</i>-Sulfonyl-1,2,3-oxathiazolidine-2-oxide Agents
  作者：Zhengxu Han、Dhileepkumar Krishnamurthy、Paul Grover、Q. Kevin Fang、Chris H. Senanayake

  DOI：10.1021/ja0200692

  日期：2002.7.1

  Simple and practical asymmetric synthesis of functionally differentiated aminoindanol based endo-N-sulfonyl 1,2,3-oxathiazolidine-2-oxide as sulfinyl transfer agents are developed. The importance of these new and unique sulfinyl transfer reagents are exemplified by the expedient production of several sulfinamide ligands, including either enantiomer of (R)-tert-butanesulfinamide in excellent yields and enantiopurities.
• Asymmetric Synthesis of Sulfinamides Using (−)-Quinine as Chiral Auxiliary
  作者：Yongda Zhang、Sampada Chitale、Navneet Goyal、Guisheng Li、Zhengxu S. Han、Sherry Shen、Shengli Ma、Nelu Grinberg、Heewon Lee、Bruce Z. Lu、Chris H. Senanayake

  DOI：10.1021/jo201825b

  日期：2012.1.6

  A process has been designed and demonstrated for the asymmetric synthesis of sulfinamides using quinine as auxiliary. A variety of chiral sulfinamides including N-alkyl sulfinamides with diverse structure were prepared in good yields and excellent enantioselectivity starting from easily available and inexpensive reagents. The auxiliary quinine could be recovered and recycled.