(R_S)-N-(tert-butanesulfinyl)butan-2-imine | 318498-72-5

• 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_S)-N-(tert-butanesulfinyl)butan-2-imine
• 英文别名: (R)-N-butan-2-ylidene-2-methylpropane-2-sulfinamide
• CAS: 318498-72-5
• 化学式: C₈H₁₇NOS
• 分子量: 175.295
• InChiKey: FCWXOBQEDLCCGF-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (R_S)-N-(tert-butanesulfinyl)butan-2-imine 在 碳酸氢钠 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 84.0h， 生成 (R,R_S)-N-(tert-butylsulfinyl)-2-amino-2-methylbutanoic acid
  参考文献：
  名称：

  Base-promoted diastereoselective addition of nitromethane and nitroethane to N-tert-butylsulfinyl imines: synthesis of N-protected α-amino acids and amino ketones

  摘要：

  DOI：

  10.1016/j.tetasy.2014.01.010
• 作为产物：
  描述：

  丁酮 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (R_S)-N-(tert-butanesulfinyl)butan-2-imine
  参考文献：
  名称：

  Diastereoselective allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols

  摘要：

  N-叔丁基磺酰亚胺与烯丙醇在钯催化下的烯丙基化和环丙基化以反-对映选择性的方式进行。

  DOI：

  10.1039/c4cc02317j

文献信息

• Indium-Promoted Diastereo- and Regioselective Propargylation of Chiral Sulfinylimines
  作者：M. Jesús García-Muñoz、Flavia Zacconi、Francisco Foubelo、Miguel Yus

  DOI：10.1002/ejoc.201201410

  日期：2013.3

  The authors thank the Spanish Ministerio de Ciencia e Innovacion (MICINN) (grant numbers CTQ2007-65218, Consolider Ingenio 2010-CSD-2007-00006 and CTQ2011-24165), the Generalitat Valenciana (PROMETEO/2009/039), the Fondos Europeos para el Desarrollo Regional (FEDER)) and the University of Alicante for financial support.

  作者感谢西班牙国家科学与创新部长 (MICINN)（授权号 CTQ2007-65218、Consolider Ingenio 2010-CSD-2007-00006 和 CTQ2011-24165）、Generalitat Valenciana (PROMETEO/2909), el Desarrollo Regional (FEDER)) 和阿利坎特大学的财政支持。
• Highly efficient asymmetric construction of quaternary carbon-containing homoallylic and homopropargylic amines
  作者：Tao Guo、Ran Song、Bin-Hua Yuan、Xiao-Yang Chen、Xing-Wen Sun、Guo-Qiang Lin

  DOI：10.1039/c3cc42481b

  日期：——

  A highly efficient method for the asymmetric synthesis of chiral quaternary carbon-containing homoallylic and homopropargylic amines under mild conditions was achieved with good yields and high diastereoselectivities.

  在温和条件下，一种高效的不对称合成含有手性季碳的同烯丙基和同炔丙基胺的方法被实现，具有良好的产率和高度对映选择性。
• Direct synthesis of chiral aziridines from N-tert-butyl-sulfinylketimines
  作者：Daniel Morton、David Pearson、Robert A. Field、Robert A. Stockman

  DOI：10.1039/b601527a

  日期：——

  of a range of variously substituted chiral tert-butylsulfinylketimines was achieved in good yield (41-90%), with relatively rapid reaction times (4-15 hours); their synthetic application was examined through the reaction with the ylides derived from trimethylsulfonium iodide and S-allyl tetrahydrothiophenium bromide, affording convenient access to a diverse range of highly substituted chiral aziridines

  直接制备一系列不同取代的手性叔丁基亚磺酰基酮亚胺，收率良好（41-90%），反应时间相对较快（4-15小时）；它们的合成应用通过与三甲基碘化锍和 S-烯丙基四氢噻吩溴化物衍生的叶立德的反应进行了检验，可以方便地获得各种高度取代的手性氮丙啶，产率高达 78%，脱色率 > 90%
• Metal free catalytic hydroboration of multiple bonds in methanol using N-heterocyclic carbenes under open atmosphere
  作者：Kun Wen、Jinbo Chen、Feng Gao、Pinaki S. Bhadury、Erkang Fan、Zhihua Sun

  DOI：10.1039/c3ob41499j

  日期：——

  An easy to operate method of catalytic hydroboration of unsaturated compounds has been developed with wide substrate scope. Reactions of various aldimines, ketimines, α,β-unsaturated carbonyl compounds, and alkynes were successfully executed with bis(pinacolato)diboron and N-heterocyclic carbenes in methanol without requiring a transition metal or inert atmosphere.

  一种易于操作的催化氢硼化不饱和化合物的方法已经开发出来，适用范围广泛。各种醛亚胺、酮亚胺、α,β-不饱和羰基化合物和炔烃的反应已成功在无过渡金属或惰性气氛的条件下，使用双(pinacolato)二硼和N-杂环卡宾在甲醇中进行。
• The first synthesis of N,O-protected β2,2,3,3-isoserines bearing two adjacent quaternary stereogenic centers and their corresponding β-lactams
  作者：Andrea Guerrini、Greta Varchi、Cristian Samorì、Rizzo Daniele、Battaglia Arturo

  DOI：10.1016/j.tetlet.2007.05.087

  日期：2007.7

  The reaction of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic and mandelic acids, with (S-R,?)-tert-butyl sulfinyl ketimines, derived from butan-2-one, pentan-2-one, and decan-2-one, afforded conformation ally restrained beta(2,2,3,3) -isoserines bearing two adjacent quaternary stereogenic centers in the form of N-sulfinyl protected 1'-amino-dioxolan-4-ones. The selective acid-induced removal of the sulfinyl protecting group provided the corresponding 1'-aminodioxolanones, whose base-induced cyclization afforded the corresponding chiral tetra-substituted 3-hydroxy-beta-lactams. The synthesis of a dipeptide by reaction coupling between the 1'-aminodioxolanone (2S,5R,1'R)-19 and N,N-dimethylglycine was successfully achieved. (C) 2007 Elsevier Ltd. All rights reserved.