(S)-(+)-S-甲基-S-苯亚磺酰亚胺 | 33903-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-(+)-S-甲基-S-苯亚磺酰亚胺
• 中文别名: (S)-(+)-s-甲基-s-苯基磺脒；(R)-(+)-S-甲基-S-苯亚磺酰亚胺；(S)-(+)-S-甲基-S-苯亚砜亚胺
• 英文名称: (S)-S-methyl-S-phenylsulfoximine
• 英文别名: S-methyl-S-phenyl-sulfoximine；(S)-imino(methyl)(phenyl)-λ⁶-sulfanone；(S)-methyl phenyl sulfoximine；methyl phenyl sulfoximine；(S)-(+)-S-Methyl-S-phenylsulfoximine；imino-methyl-oxo-phenyl-λ6-sulfane
• CAS: 33903-50-3；60933-65-5；4381-25-3
• 化学式: C₇H₉NOS
• 分子量: 155.221
• InChiKey: YFYIDTVGWCYSEO-JTQLQIEISA-N

物化性质

• 熔点：
  30-32°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S24/25
• 危险类别码：
  R22
• 海关编码：
  2925290090
• WGK Germany：
  3
• 危险性防范说明：
  P264,P270,P301+P312,P330,P501
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  (S)-(+)-S-甲基-S-苯亚磺酰亚胺 在 盐酸 、 m-C₆H₄CO₃H 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.0h， 以93%的产率得到苯甲砜
  参考文献：
  名称：

  A Method for the Conversion of Sulfoximines to Sulfones: Application to Polymer-Bound Sulfoximines and to the Synthesis of Chiral Sulfones

  摘要：

  Reaction of N-alkyl, N-aryl, and N-H sulfoximines with m-chloroperbenzoic acid cleanly gives the corresponding sulfones in high yield. In the case of the cleavage of N-alkyl and N-arylsulfoximines, formation of the corresponding nitroso compounds as the other reaction product was proven. Starting from enantio- and diastereopure sulfoximines, a number of chiral sulfones, including the axially chiral sulfone 6 and the sulfonyl-functionalized homoallylic alcohol 8, have been prepared. Reaction of the enantiopure sulfoximine 30 with Merrifield resin gave the polymer-bound sulfoximine 32. Oxidative cleavage of 32 afforded the sulfone 16 in high yield. Deprotonation of the sulfoximine resin 32 and reaction of Li-32 with benzaldehyde and propanal furnished the beta-hydroxysulfoximine resins 33a and 33b, respectively. Oxidative cleavage of 33a and 33b readily afforded the beta-hydroxy sulfones 14a and 14b, respectively.

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1457::aid-ejoc1457>3.0.co;2-g
• 作为产物：
  描述：

  甲基苯基亚砜 在 sodium azide 、 硫酸 、 (1S)-(+)-10-camphorsulfonic acid 作用下， 以 氯仿 为溶剂， 生成 (S)-(+)-S-甲基-S-苯亚磺酰亚胺
  参考文献：
  名称：

  通过亚砜基yl，醛和烯酮的反应不对称合成γ-内酯

  摘要：

  提出了一种通过对映体富集的亚砜基磺酸盐，醛和烯酮的反应对映选择性合成γ-内酯的方法。使对映体富集（98％ee）的氨基ulf酸叶立德与各种醛（芳族和脂族）和双取代的烯酮反应，导致形成α，β-取代的γ-内酯，具有中等至非常好的非对映选择性（dr 95：5），对映体过量最多为ee的79％。在富含对映体的氨基亚砜基ox与异丁醛和各种烷基芳基烯酮的反应中观察到最佳对映选择性水平。

  DOI：

  10.1016/j.tetlet.2014.05.130

文献信息

• [EN] SULFOXIMINE SUBSTITUTED PYRROLOTRIAZINES FOR PHARMACEUTICAL COMPOSITIONS<br/>[FR] PYRROLOTRIAZINES À SUBSTITUTION SULFOXIMINE POUR COMPOSITIONS PHARMACEUTIQUES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2015091156A1

  公开（公告）日：2015-06-25

  This invention relates to novel sulfoximine substituted pyrrolotriazine derivatives of formula wherein Ar, R1 and R2 are as defined in the description and claims, and their use as MNK1 (MNK1 a or MNK1 b) and/or MNK2 (MNK2a or MNK2b) kinase inhibitors, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment or amelioration of MNK1 (MNK1 a or MNK1 b) and/or MNK2 (MNK2a or MNK2b) mediated disorders.

  这项发明涉及一种新型的噻氧亚胺取代吡咯三嗪衍生物，其化学式中Ar、R1和R2的定义如描述和权利要求中所定义，并且它们作为MNK1（MNK1 a或MNK1 b）和/或MNK2（MNK2a或MNK2b）激酶抑制剂的用途，含有这些化合物的药物组合物，以及将其用作治疗或改善MNK1（MNK1 a或MNK1 b）和/或MNK2（MNK2a或MNK2b）介导的疾病的药剂的方法。
• Ｎ-이미도일 설폭시민 유도체 및 이의 제조 방법
  申请人：KNU-Industry Cooperation Foundation 강원대학교산학협력단(220040088571) BRN ▼221-82-10213

  公开号：KR20170109274A

  公开（公告）日：2017-09-29

  본 발명은 리간드와 카이랄 보조제로 사용되는 중요한 구조의 성질을 띄고있어 다양한 연구분야에서 이용가능한 신규의 N-이미도일 설폭시민 유도체 및 이의 제조방법에 관한 것으로, 보다 상세하게는 구리 촉매 존재 하에 알카인 유도체, 아자이드 유도체 및 N-설폭시민 유도체를 반응시켜 설폭시민의 질소 원자에 탄소-질소 결합 작용기가 도입된 N-이미도일 설폭시민 유도체를 효율적으로 제조하는 방법 및 이에 따라 제조된 N-이미도일 설폭시민 유도체에 관한 것이다.

  本发明涉及一种具有重要结构特性的用作配体和手性助剂的新型N-亚甲基硫醚衍生物及其制备方法，可在各种研究领域中使用。更详细地说，涉及在铜催化剂存在下，通过使烷基衍生物、偶氮衍生物和N-亚甲基硫醚衍生物反应，有效制备引入碳-氮键合作用基团的N-亚甲基硫醚衍生物的方法，以及由此制备的N-亚甲基硫醚衍生物。
• Asymmetric intramolecular Diels-Alder reactions of sulfoximine-activated trienes
  作者：Donald Craig、Neil J. Geach、Christopher J. Pearson、Alexandra M.Z. Slawin、Andrew J.P. White、David J. Williams

  DOI：10.1016/0040-4020(95)00267-c

  日期：1995.5

  A series of N-substituted sulfoximidoyl-1,6,8-nonatrienes and 1,7,9-decatrienes were synthesised and subjected to thermal intramolecular Diels-Alder (IMDA) reactions to give diastereomeric mixtures of substituted bicyclo[4.3.0]nonanes and -[4.4.0]decanes. The reactions showed varying selectivities. Endo/exo selectivity was interpreted in terms of a combination of steric factors and the asynchronous

  合成了一系列的N-取代的亚磺酰亚胺基-1,6,8-壬烯和1,7,9-癸二烯，并进行热分子内Diels-Alder（IMDA）反应，得到取代的双环[4.3.0]壬烷的非对映异构体混合物和-[4.4.0]癸烷。反应显示出不同的选择性。内/外选择性是根据空间因素和环加成反应的异步性质的组合来解释的。通过考虑二烯在构象扩展的乙烯基亚砜亚胺二烯亲和体的较少受阻面上的进攻，可以合理化非对面选择性。
• Sulfoximines: A Reusable Directing Group for Chemo- and Regioselective ortho CH Oxidation of Arenes
  作者：M. Ramu Yadav、Raja K. Rit、Akhila K. Sahoo

  DOI：10.1002/chem.201200092

  日期：2012.4.27

  Sulfoximines direct: A new protocol for the chemo‐ and regioselective ortho CH acetoxylation of arenes in N‐benzoylated sulfoximines is reported. The sulfoximine directing group is easily detached from the CH oxidation product through acid‐promoted hydrolysis, isolated, and reused (see scheme). The meta‐substituted phenols are synthesized following this strategy and the stereointegrity of the sulfoximine

  亚磺酰亚胺直接：用于化疗和区域选择性的新协议邻Ç 中的H芳烃的乙酰氧基化Ñ报道-benzoylated亚磺酰亚胺。通过酸促进的水解作用，磺胺嘧啶导向基很容易从CH氧化产物中分离出来，进行分离和再利用（参见方案）。该元取代酚遵循这一发展战略和亚砜的stereointegrity在这一转变被保留合成。还证明了甲基的C（sp 3）H乙酰氧基化。
• Metal-Free, Phosphonium Salt-Mediated Sulfoximination of Azine <i>N</i>-Oxides: Approach for the Synthesis of <i>N</i>-Azine Sulfoximines
  作者：Sravan Kumar Aithagani、Mukesh Kumar、Mahipal Yadav、Ram A. Vishwakarma、Parvinder Pal Singh

  DOI：10.1021/acs.joc.6b00593

  日期：2016.7.15

  method for the synthesis of N-azine sulfoximines by the nucleophilic substitution of azine N-oxides with NH-sulfoximines. The present method works at room temperature with wide functional group compatibility and gives several unprecedented N-azine sulfoximines. The reaction conditions were also found suitable with enantiopure substrates and furnished products without any racemization. It also finds

  在本文中，我们报道了一种简单且无金属的方法，该方法通过用NH-亚砜肟酮亲核取代N-嗪氮氧化物来合成N-嗪亚砜肟。本方法在室温下具有宽泛的官能团相容性，并提供了几种前所未有的N-嗪亚磺酰亚胺。还发现反应条件适用于对映纯底物和提供的产物，没有任何消旋作用。还发现了其在基于嗪的功能分子如2,2'-联吡啶，1,10-菲咯啉和奎宁的磺化中的应用。

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