(S)-(+)-N-benzylidene-2,4,6-trimethylphenylsulfinamide | 855475-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(+)-N-benzylidene-2,4,6-trimethylphenylsulfinamide
• 英文别名: (S)-(+)-N-(benzylidene)-2,4,6-trimethylbenzenesulfinamide；(S,E)-N-benzylidene-2,4,6-trimethylbenzenesulfinamide；(NE,S)-N-benzylidene-2,4,6-trimethylbenzenesulfinamide
• CAS: 855475-24-0
• 化学式: C₁₆H₁₇NOS
• 分子量: 271.383
• InChiKey: KPPLHRZIGTXNOR-OXRZLYTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-N-benzylidene-2,4,6-trimethylphenylsulfinamide 在 甲基溴化镁 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.5h， 生成 diethyl (2S,3R)-(-)-3-phenylaziridine-2-phosphonate
  参考文献：
  名称：

  Improved Asymmetric Synthesis of Aziridine 2-Phosphonates Using (S)-(+)-2,4,6-Trimethylphenylsulfinamide

  摘要：

  The aza-Darzens reaction of lithium diethyl iodomethylphosphonate with enantiopure N-(2,4,6-trimethylphenylsulfinyl)imines affords a single diastereomeric N-sulfinylaziridine 2-phosphonate which, on treatment with MeMgBr, gives the corresponding NH-aziridine 2-phosphonate chiral building blocks. An improved asymmetric synthesis of (S)-(+)-2,4,6-trimethylphenylsulfinamide is also given.

  DOI：

  10.1021/jo030142m
• 作为产物：
  描述：

  (R_S,1S,2R)-(-)-2,4,6-trimethylbenzenesulfinic acid 1-(2,4,6-trimethylbenzenesulfonylamino)indan-2-yl ester 在 titanium(IV) tetraethanolate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-(+)-N-benzylidene-2,4,6-trimethylphenylsulfinamide
  参考文献：
  名称：

  Improved Asymmetric Synthesis of Aziridine 2-Phosphonates Using (S)-(+)-2,4,6-Trimethylphenylsulfinamide

  摘要：

  The aza-Darzens reaction of lithium diethyl iodomethylphosphonate with enantiopure N-(2,4,6-trimethylphenylsulfinyl)imines affords a single diastereomeric N-sulfinylaziridine 2-phosphonate which, on treatment with MeMgBr, gives the corresponding NH-aziridine 2-phosphonate chiral building blocks. An improved asymmetric synthesis of (S)-(+)-2,4,6-trimethylphenylsulfinamide is also given.

  DOI：

  10.1021/jo030142m

文献信息

• Multicomponent Synthesis of Chiral Sulfinimines
  作者：Caroline Roe、Heather Hobbs、Robert A. Stockman

  DOI：10.1002/chem.201003222

  日期：2011.2.25

  Two oxathiozolidine‐S‐oxide templates have been developed and used in a four‐component coupling protocol for the synthesis of a wide range of chiral sulfinimines in high enantiomeric excesses. The templates can be synthesized from cheap commodity chemicals in three steps in high yields. Furthermore the template is easily recovered in high yields for recycling.

  已开发出两个氧杂硫唑烷-S-氧化物模板，并用于四组分偶联方案中，用于合成大量对映体过量的手性亚氨嘧啶。模板可以由廉价的商品化学品分三步以高收率合成。此外，可以容易地以高收率回收模板以进行回收。
• Asymmetric radical alkylation of N-sulfinimines under visible light photocatalytic conditions
  作者：Alberto F. Garrido-Castro、Houcine Choubane、Mortada Daaou、M. Carmen Maestro、José Alemán

  DOI：10.1039/c7cc03724d

  日期：——

  derivatives to N-sulfinimines with complete diastereoselectivity and moderate to good yields is presented. This is the first asymmetric photocatalytic addition to N-sulfinimines under visible light irradiation with smooth conditions and functional group tolerance.

  在这种交流中，提出了一种新的光催化策略，用于将烷基自由基衍生物添加到N-亚磺胺中，具有完全的非对映选择性和中等至良好的产率。这是在光滑条件和官能团耐受性的可见光照射下，N-亚磺胺类化合物的首次不对称光催化加成反应。
• Asymmetric Synthesis of <i>syn</i>-α-Substituted β-Amino Ketones by Using Sulfinimines and Prochiral Weinreb Amide Enolates
  作者：Franklin A. Davis、Minsoo Song

  DOI：10.1021/ol0708166

  日期：2007.6.1

  Syn-alpha-substituted beta-amino Weinreb amides are new chiral building blocks for asymmetric synthesis of syn-alpha-substituted beta-amino acids, aldehydes, and ketones and are prepared by addition of prochiral lithium enolates of Weinreb amides to sulfinimines (N-sulfinyl imines).

  顺式-α-取代的β-氨基Weinreb酰胺是用于不对称合成顺式-α-取代的β-氨基酸，醛和酮的新的手性结构单元，是通过将Weinreb酰胺的前手性烯醇锂加入亚磺胺制得的（N-亚砜亚胺）。
• Nucleophilic Trifluoromethylation of Imines Using the CF₃I/TDAE Reagent
  作者：Wei Xu、William R. Dolbier

  DOI：10.1021/jo050483v

  日期：2005.6.1

  The nucleophilic trifluoromethylation reagent derived from CF3I and tetrakis(dimethylamino)ethylene (TDAE) was found to be effective in addition to both N-tosyl aldimines and N-tolyl sulfinimines, the latter reaction exhibiting very good diastereoselectivity.
• Improved Asymmetric Synthesis of Aziridine 2-Phosphonates Using (<i>S</i>)-(+)-2,4,6-Trimethylphenylsulfinamide
  作者：Franklin A. Davis、Tokala Ramachandar、Yongzhong Wu

  DOI：10.1021/jo030142m

  日期：2003.9.1

  The aza-Darzens reaction of lithium diethyl iodomethylphosphonate with enantiopure N-(2,4,6-trimethylphenylsulfinyl)imines affords a single diastereomeric N-sulfinylaziridine 2-phosphonate which, on treatment with MeMgBr, gives the corresponding NH-aziridine 2-phosphonate chiral building blocks. An improved asymmetric synthesis of (S)-(+)-2,4,6-trimethylphenylsulfinamide is also given.