S-(+)-2-methyl-N-p-tosylaziridine | 119461-40-4

• 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-(+)-2-methyl-N-p-tosylaziridine
• 英文别名: (S)-2-methyl-1-tosylaziridine；(S)-N-tosyl-2-methylaziridine；(S)-N-(p-toluenesulfonyl)-2-methylaziridine；(S)-1-Tosyl-2-methylaziridine；(2S)-2-methyl-1-(4-methylphenyl)sulfonylaziridine
• CAS: 119461-40-4
• 化学式: C₁₀H₁₃NO₂S
• 分子量: 211.285
• InChiKey: DRZLZRGBQZRSJI-FTNKSUMCSA-N

物化性质

• 熔点：
  56-58 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  326.2±35.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、可溶于二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-(+)-2-methyl-N-p-tosylaziridine 在 sodium naphthalenide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.25h， 生成 (S)-2-甲基氮丙啶
  参考文献：
  名称：

  Scalable Synthesis of N-Acylaziridines from N-Tosylaziridines

  摘要：

  N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives. The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N-tosylaztridines and reprotection with N-hydroxysuccinimide derivatives is described. Mono- and disubstituted aziridines perform well, with complete retention of stereochemical purity. The consistently moderate yields are linked to the N-tosylaziridine deprotection step, while acylation with N-hydroxysuccinimide derivatives is highly efficient.

  DOI：

  10.1021/jo401267j
• 作为产物：
  描述：

  (S)-2-(4-甲基苯基磺酰胺基)丙酸甲酯 在 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 S-(+)-2-methyl-N-p-tosylaziridine
  参考文献：
  名称：

  An efficient synthetic approach for N–C bond formation from (S)-amino acids: an easy access to cis-2,5-disubstituted chiral piperazines

  摘要：

  本文描述了一种高效的合成策略，用于构建来源于对映体纯的顺式-2,5-二取代手性哌嗪的氨基酸。铜催化的自发区域选择性开环和闭环反应，以及钯介导的N–C键形成，均来自N-托磺酰卤代氨基衍生物，是获取二取代哌嗪的关键步骤。

  DOI：

  10.1039/c3ra42309c

文献信息

• An easy one-step procedure for the synthesis of novel β-functionalised tellurides
  作者：Damiano Tanini、Anna Grechi、Silvia Dei、Elisabetta Teodori、Antonella Capperucci

  DOI：10.1016/j.tet.2017.07.061

  日期：2017.9

  Novel β-hydroxy-,β-amino- and β-mercapto- dialkyl- and phenyl-alkyl tellurides have been achieved through regioselective ring opening reactions of oxiranes, aziridines and thiiranes with different Te-nucleophiles, including tellurosilanes. Tellurium-125 NMR chemical shifts of selected compounds have been measured.

  通过环氧乙烷，氮丙啶和噻喃与不同的Te-亲核试剂（包括碲硅烷）的区域选择性开环反应，已经获得了新型的β-羟基-，β-氨基-和β-巯基-二烷基-和苯基-烷基碲化物。已对所选化合物的碲125 NMR化学位移进行了测量。
• Synthesis of Functionalised Piperidines Through a [3 + 3] Cycloaddition Strategy
  作者：Simon J. Hedley、Wesley J. Moran、Alexander H. G. P. Prenzel、David A. Price、Joseph P. A. Harrity

  DOI：10.1055/s-2001-17443

  日期：——

  A novel approach to functionalised piperidines is described through a [3 + 3] cycloaddition reaction of aziridines with Pd-trimethylenemethane complexes. Importantly, the employment of enantiomerically pure aziridines (prepared in three steps from the appropriate amino acids) allows the corresponding piperidines to be furnished in enantiomerically pure form. Additionally, the application of this technique in the total synthesis of (-)-pseudoconhydrine is described.

  描述了一种通过氮杂环丙烷与Pd-三甲基亚甲基复合物的[3 + 3]环加成反应制备功能化哌啶的新方法。重要的是，通过使用手性纯氮杂环丙烷（从适当的氨基酸经过三步制备），可以使相应的哌啶以手性纯形式获得。此外，还描述了这一技术在(-)-伪氢化可的因的全合成中的应用。
• Late-Stage Functionalization of Aromatic Acids with Aliphatic Aziridines: Direct Approach to Form β-Branched Arylethylamine Backbones
  作者：Kehan Zhou、Yan Zhu、Weitai Fan、Yujie Chen、Xu Xu、Jingyu Zhang、Yingsheng Zhao

  DOI：10.1021/acscatal.9b01347

  日期：2019.8.2

  an ortho-C(sp2) atom of aromatic acids with aliphatic aziridines to construct the β-arylethylamine skeleton via C–H activation has been developed. The reaction proceeded under mild conditions with great substrate scope. Meanwhile, the β-arylethylamine skeleton in drugs or bioactive compounds could be easily generated in a single step. A catalytic amount of cesium carbonate was crucial to realizing

  已开发出钯催化的羧酸定向的芳香族酸的邻位C（sp 2）原子与脂肪族氮丙啶的交叉偶联，以通过C–H活化来构建β-芳基乙胺骨架。反应在温和的条件下在较大的底物范围内进行。同时，药物或生物活性化合物中的β-芳基乙胺骨架很容易在一个步骤中生成。催化量的碳酸铯对于实现选择性β-芳基乙胺合成至关重要。
• Tandem aziridine ring opening-disulfide formation-reduction-Michael addition in one-pot mediated by tetrathiomolybdate
  作者：Devarajulu Sureshkumar、Thanikachalam Gunasundari、Srinivasan Chandrasekaran

  DOI：10.1016/j.tet.2015.04.003

  日期：2015.9

  A detailed study of tetrathiomolybdate mediated tandem regio- and stereoselective ring opening of aziridine, disulfide formation, reduction of disulfide bond and Michael reaction in a one-pot operation is reported. This constitutes four reactions that take place in one-pot operation. In the reaction of [BnEt3N]4MoS4 with an aziridine derived from cyclohexene and in the absence of Michael acceptor intermediates

  一锅操作中，详细报道了四硫代钼酸盐介导的氮丙啶串联区域和立体选择性开环，二硫键形成，二硫键还原和迈克尔反应的详细研究。这构成了一锅操作中发生的四个反应。在[BnEt 3 N] 4 MoS 4的反应中在不存在迈克尔受体的情况下，用衍生自环己烯的氮丙啶的化合物分离并充分表征了磺酰胺基二硫化物和磺酰胺基硫醇。还已经表明，可以在环氧化物存在下选择性地打开氮丙啶环。通过掺入合适的迈克尔受体作为底物的一部分，可以进行分子内的1,4-加成，以高收率合成含硫的无环环状氨基酸酯衍生物和硫代双环[3.3.1]壬烷衍生物。 。
• Tandem Ring-Opening/Closing Reactions of <i>N</i>-Ts Aziridines and Aryl Propargyl Alcohols Promoted by <i>t</i>-BuOK
  作者：Liang Wang、Qi-Bin Liu、Duo-Sheng Wang、Xin Li、Xiu-Wen Han、Wen-Jing Xiao、Yong-Gui Zhou

  DOI：10.1021/ol802862p

  日期：2009.3.5

  t-BuOK was found to be an effective promoting reagent for tandem ring-opening/closing reactions of various N-Ts aziridines and aryl propargyl alcohols to afford dihydroxazine derivatives in moderate to good yields. A plausible reaction mechanism has been proposed.

  发现t- BuOK是一种有效的促进剂，用于各种N- Ts氮丙啶和芳基炔丙醇的串联开环/闭环反应，以中等至良好的产率提供二氢恶嗪衍生物。已经提出了合理的反应机理。