(3,3-dimethyl-1-tosylazirin-2-yl)methanol | 210972-38-6

• 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: (3,3-dimethyl-1-tosylazirin-2-yl)methanol
• 英文别名: (3,3-dimethyl-1-tosylaziridin-2-yl)methanol；3,3-Dimethyl-1-[(4-methylphenyl)sulfonyl]-2-aziridinemethanol；[3,3-Dimethyl-1-(4-methylphenyl)sulfonylaziridin-2-yl]methanol
• CAS: 210972-38-6
• 化学式: C₁₂H₁₇NO₃S
• 分子量: 255.338
• InChiKey: VWNVVKVJQROHDH-UHFFFAOYSA-N

物化性质

• 沸点：
  389.5±44.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3,3-dimethyl-1-tosylazirin-2-yl)methanol 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 以63%的产率得到4-methyl-N-(2-(oxiran-2-yl)propan-2-yl)benzenesulfonamide
  参考文献：
  名称：

  来自环氧磺酰胺和甲基二甲基ulf的3-羟基吡咯烷。

  摘要：

  N-甲苯磺酰基保护的3-羟基吡咯烷是通过使二甲基亚砜基亚甲基与易得的环氧磺酰胺反应而制备的。

  DOI：

  10.1039/b606583j
• 作为产物：
  描述：

  chloroamine-T 、 异戊烯醇 在 phenyltrimethylammonium tribromide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以78%的产率得到(3,3-dimethyl-1-tosylazirin-2-yl)methanol
  参考文献：
  名称：

  从 β-烷氧基氮丙啶和有机锂试剂合成取代的烯丙基磺酰胺

  摘要：

  描述了有机锂介导的（从无环烯丙醇衍生的 3-甲氧基 N-甲苯磺酰基氮丙啶转化为取代的烯丙磺酰胺）的范围和限制。

  DOI：

  10.1055/s-2008-1032013

文献信息

• Twofold Radical-Based Synthesis of <i>N</i>,<i>C</i>-Difunctionalized Bicyclo[1.1.1]pentanes
  作者：Helena D. Pickford、Jeremy Nugent、Benjamin Owen、James. J. Mousseau、Russell C. Smith、Edward A. Anderson

  DOI：10.1021/jacs.1c04180

  日期：2021.7.7

  Bicyclo[1.1.1]pentylamines (BCPAs) are of growing importance to the pharmaceutical industry as sp3-rich bioisosteres of anilines and N-tert-butyl groups. Here we report a facile synthesis of 1,3-disubstituted BCPAs using a twofold radical functionalization strategy. Sulfonamidyl radicals, generated through fragmentation of α-iodoaziridines, undergo initial addition to [1.1.1]propellane to afford iodo-BCPAs;

  双环[1.1.1] pentylamines（BCPAs）是重要性日益增加，以制药业作为藻3个苯胺和富含的bioisosters ñ -叔丁基的基团。在这里，我们报告了使用双重自由基功能化策略轻松合成 1,3-二取代 BCPA。磺胺基自由基，通过 α-碘氮丙啶的碎裂产生，经过初始添加到 [1.1.1] 丙烷中，得到碘-BCPA；然后通过甲硅烷基介导的 Giese 反应将这些产物中新形成的 C-I 键功能化。这种化学反应也可以顺利转化为 1,3-二取代碘-BCP。可容纳多种自由基受体和碘-BCPA，可直接获取一系列有价值的类苯胺等排体。
• Tetrathiomolybdate Mediated Rearrangement of Aziridinemethanol Tosylates: A Thia-Aza-Payne Rearrangement
  作者：Devarajulu Sureshkumar、Srinivasamurthy Koutha、Venkataraman Ganesh、Srinivasan Chandrasekaran

  DOI：10.1021/jo100640w

  日期：2010.8.20

  Aziridinemethanol sulfonate esters react with tetrathiomolybdate 1 to give thiirane derivatives as the major product and cyclic disulfides as minor product under mild reaction conditions via an unprecedented thia-aza-Payne-type rearrangement. Interestingly, when the reaction of 1 was carried out with 2-aziridino-cyclohexanol derivatives it resulted in the formation of thia-bicyclo[3.1.1]heptane or

  氮丙啶甲醇磺酸酯与四硫代钼酸盐1反应，在温和的反应条件下，通过空前的硫杂-氮杂-佩因类型的重排，以硫杂环丁烷衍生物为主要产物，环状二硫键为次要产物。有趣的是，当1与2-叠氮基-环己醇衍生物进行反应时，会导致生成噻二环[3.1.1]庚烷或二硫二环[3.2.1]辛烷衍生物。
• One-Pot Synthesis of β-Amino/β-Hydroxy Selenides and Sulfides from Aziridines and Epoxides
  作者：Srinivasan Chandrasekaran、Venkataraman Ganesh

  DOI：10.1055/s-0029-1216960

  日期：2009.10

  Diaryl disulfides and diselenides undergo facile cleavage on treatment with rongalite (sodium hydroxymethanesulfinate) to generate the corresponding thiolate and selenolate species in situ, which effect the ring opening of aziridines and epoxides in a regio­selective manner. A simple, mild, cost-effective protocol has been developed to prepare β-amino and β-hydroxy sulfides and selenides in a one-pot operation.

  二芳基二硫和二硒化物在与隆伽利特（羟甲基亚磺酸钠）反应时容易发生裂解，生成相应的硫醇盐和硒醇盐物种，这些物质能够选择性地促进氮杂环和环氧化物的开环反应。已开发出一种简单、温和、成本效益高的一锅法操作，用于制备β-氨基和β-羟基硫化物和硒化物。
• Regio- and Stereospecific Synthesis of β-Sulfonamidodisulfides and β-Sulfonamidosulfides from Aziridines using Tetrathiomolybdate as a Sulfur Transfer Reagent
  作者：Devarajulu Sureshkumar、Thanikachalam Gunasundari、Venkataraman Ganesh、Srinivasan Chandrasekaran

  DOI：10.1021/jo0624389

  日期：2007.3.1

  comprehensive study of a general and effective one-step procedure for the synthesis of β-sulfonamidodisulfides directly from N-tosyl aziridines in a regio- and stereospecific manner under neutral conditions without the use of any Lewis acid or base has been reported. This methodology is extended to the synthesis of an optically pure cyclic seven-membered disulfide 29. Synthesis of a variety of β-sulfonamidosulfides

  已经报道了在中性条件下不使用任何路易斯酸或碱的情况下以区域和立体特异性方式直接由N-甲苯磺酰基氮丙啶直接合成β-磺酰胺基二硫化物的一般有效步骤的综合研究。该方法学扩展到光学纯的环状七元二硫键29的合成。还报道了在一个罐中合成多个涉及串联，多步反应的β-磺酰胺基硫化物。
• Direct Synthesis of Functionalized Unsymmetrical β-Sulfonamido Disulfides by Tetrathiomolybdate Mediated Aziridine Ring-Opening Reactions
  作者：Devarajulu Sureshkumar、Venkataraman Ganesh、Ravindran Sasitha Vidyarini、Srinivasan Chandrasekaran

  DOI：10.1021/jo901528e

  日期：2009.10.16

  Direct synthesis of unsymmetrical beta-sulfonamido disulfides by ring-opening of aziridines by using benzyltriethyl-ammonium tetrathiomolybdate 1 as a sulfur transfer reagent in the presence of symmetrical disulfides as thiol equivalents has been reported. Reaction of benzyl and alkyl disulfides gave unsymmetrical beta-sulfonamido disulfides as the only product in very good yields. From the Study, it has been observed that aryl disulfides containing p-NO2, p-Cl, and p-CN led to the formation of the corresponding beta-aminosulfides as the exclusive products. However, un-substituted aryl disulfides and the one containing electron-donating substituents (p-Me) provide a mixture of beta-sulfonamido mono- and disulfides as the products.