2-(溴甲基)-1-(甲磺酰基)氮丙啶 | 497239-67-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: 2-(溴甲基)-1-(甲磺酰基)氮丙啶
• 英文名称: 2-(bromomethyl)-1-(methanesulfonyl)aziridine
• 英文别名: 2-(Bromomethyl)-1-methylsulfonylaziridine
• CAS: 497239-67-5
• 化学式: C₄H₈BrNO₂S
• 分子量: 214.083
• InChiKey: LMPPGETVFWNFAU-UHFFFAOYSA-N

物化性质

• 沸点：
  292.3±32.0 °C(Predicted)
• 密度：
  1.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-(溴甲基)-1-(甲磺酰基)氮丙啶 在 sodium azide 、 silica gel 作用下， 以 水 为溶剂， 以81%的产率得到N-(2-azido-1-(azidomethyl)ethyl)methanesulfonamide
  参考文献：
  名称：

  Ring opening of 2-(bromomethyl)-1-sulfonylaziridines towards 1,3-heteroatom substituted 2-aminopropane derivatives

  摘要：

  1,3-Heteroatom substituted 2-aminopropane derivatives have been prepared from 2-(bromomethyl)-1-sulfonylaziridines for the first time using sodium azide or different potassium phenoxides in water in the presence of silica gel. The applicability of 1-arenesulfonyl-2(bromomethyl)aziridines for the synthesis of functionalized sulfonamides has also been demonstrated towards different 1,3-dialkoxy-2(tosylamino)propanes and 1,3-dialkylthio-2-(tosylamino)propanes upon treatment with the appropriate sodium alkoxide or sodium alkylthiolate in the corresponding alcohol or in methanol, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.036
• 作为产物：
  描述：

  intermed 2c 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 2-(溴甲基)-1-(甲磺酰基)氮丙啶
  参考文献：
  名称：

  由2-（溴甲基）-或2-（磺酰氧基甲基）氮丙啶类区域和立体控制合成新型3-磺酰胺基-2,3,4,5-四氢-1,5-苯并硫氮杂s。

  摘要：

  在K 2 CO 3存在下用2-氨基硫酚处理THF后，将2-（溴甲基）-1-磺酰基氮丙啶转化为新型的3-磺酰胺基-2,3,4,5-四氢-1,5-苯并硫氮杂s。从3-取代的2-（磺酰氧基甲基）氮丙啶开始，区域和立体控制合成反式-2-苯基-和反式4-（苯基或丙基）-3-磺酰胺基-2,3,4,5-四氢-根据磺酰氧基的性质，通过两种不同的反应途径以高收率开发了1,5-苯并硫氮杂s。

  DOI：

  10.1039/b804246m

文献信息

• A new synthesis of 1,3-difunctionalized 2-aminopropane derivatives by reaction of substituted thiourea and arylthiol derivatives with <i>N</i>-sulfonylated aziridines
  作者：Fatemeh Azizi、Gholamhossein Khalili

  DOI：10.1080/17415993.2020.1712398

  日期：2020.5.3

  ABSTRACT A new synthesis of novel 1,3-difunctionalized 2-aminopropane derivatives from N-sulfonylated aziridines is described. The reaction of 2-(bromomethyl)-1-sulfonylaziridines with substituted thiourea and arylthiol derivatives in presence MeONa in DMF at 35–40°C occurs readily to afford 2-(alkyl/arylsulfonamido)-1,3-diyl-bis(N′-phenylcarbamimidothioate) and N-(1,3-bis(arylthio)propan-2-yl)-arylsulfonamide

  摘要描述了一种从 N-磺酰化氮丙啶合成新型 1,3-双官能化 2-氨基丙烷衍生物的新方法。2-(溴甲基)-1-磺酰氮丙啶与取代的硫脲和芳硫醇衍生物在 MeONa 存在下在 DMF 中在 35–40°C 下反应容易发生，得到 2-(烷基/芳基磺酰胺)-1,3-二基-双(N '-苯基氨基甲亚氨基硫酸酯)和 N-(1,3-双(芳硫基)丙-2-基)-芳基磺酰胺化合物的产率良好。图形概要
• Synthesis and Density Functional Theory Studies of Azirinyl and Oxiranyl Functionalized Isoindigo and (3Z,3’Z)-3,3’-(ethane-1,2-diylidene)bis(indolin-2-one) Derivatives
  作者：Gholamhossein Khalili、Patrick McCosker、Timothy Clark、Paul Keller

  DOI：10.3390/molecules24203649

  日期：——

  The design and synthesis of functionalized isoindigo compounds by reaction of isoindigo with (S)-glycidyl tosylate, epibromohydrin, 2-(bromomethyl)-1-(arylsulfonyl)aziridine, and 2-(bromomethyl)-1-(alkylsulfonyl)aziridine in the presence of MeONa proceed under mild conditions in moderate yields. (3Z,3’Z)-3,3’-(Ethane-1,2-diylidene)bis(1-(oxiran-2-ylmethyl)indolin-2-one), with an extended central olefin

  通过异靛蓝与 (S)-甲苯磺酸缩水甘油酯、表溴醇、2-(溴甲基)-1-(芳基磺酰基)氮丙啶和 2-(溴甲基)-1-(烷基磺酰基)氮丙啶反应设计和合成功能化异靛蓝化合物MeONa 的存在在温和条件下以中等产率进行。(3Z,3'Z)-3,3'-(Ethane-1,2-diylidene)bis(1-(oxiran-2-ylmethyl)indolin-2-one)，具有扩展的中心烯烃 π-共轭部分是也与甲基-环氧乙烷反应得到相应的 N,N'-二取代衍生物。具有各种吸电子取代基（包括氮丙啶、环氧乙烷、腈、羰基和磺酸盐）的假设异靛-噻吩 DA 分子的 DFT 和 TD-DFT 计算表明，官能团的接近度和强度对 HOMO 有显着影响， LUMO，垂直激发能，
• A new synthesis of 1,3-difunctionalized 2-sulfonamidopropane derivatives via regioselective ring opening reactions of 2-(bromomethyl)-1-sulfonylaziridines by substituted arylsulfonamides
  作者：Fatemeh Azizi、Gholamhossein Khalili

  DOI：10.1007/s00706-019-02546-9

  日期：2020.2

  3-diyl]bis(N-allylarylsulfonamide) and N,N′-[2-(methylsulfonamido)propane-1,3-diyl]bis(N-benzylarylsulfonamide) derivatives have been prepared from 2-(bromomethyl)-1-sulfonylaziridines for the first time using substituted arylsulfonamides in the presence of sodium methoxide under catalyst-free condition in good yields. Graphic abstract

  摘要新型功能化的N，N' -[2-（芳基磺酰胺基）丙烷-1,3-二基]双（N-烯丙基芳基磺酰胺）和N，N' -[2-（甲基磺酰胺基）丙烷-1,3-二基]双（N-苄基芳基磺酰胺）衍生物是由2-（溴甲基）-1-磺酰基氮丙啶在甲醇钠存在下，无催化剂条件下首次使用取代的芳基磺酰胺以高收率制备的。 图形摘要
• Electron transfer induced ring opening of 2-(bromomethyl)aziridines by magnesium in methanol
  作者：Kourosch Abbaspour Tehrani、Tuyen NguyenVan、Michinori Karikomi、Mario Rottiers、Norbert De Kimpe

  DOI：10.1016/s0040-4020(02)00728-7

  日期：2002.8

  Magnesium metal in methanol was used as a simple electron transfer induced ring-opening reagent of 2-(bromomethyl)aziridines to afford allylamines derivatives in 70-90% yield. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Ring opening of 2-(bromomethyl)-1-sulfonylaziridines towards 1,3-heteroatom substituted 2-aminopropane derivatives
  作者：Matthias D'hooghe、Mario Rottiers、Inge Kerkaert、Norbert De Kimpe

  DOI：10.1016/j.tet.2005.06.036

  日期：2005.9

  1,3-Heteroatom substituted 2-aminopropane derivatives have been prepared from 2-(bromomethyl)-1-sulfonylaziridines for the first time using sodium azide or different potassium phenoxides in water in the presence of silica gel. The applicability of 1-arenesulfonyl-2(bromomethyl)aziridines for the synthesis of functionalized sulfonamides has also been demonstrated towards different 1,3-dialkoxy-2(tosylamino)propanes and 1,3-dialkylthio-2-(tosylamino)propanes upon treatment with the appropriate sodium alkoxide or sodium alkylthiolate in the corresponding alcohol or in methanol, respectively. (c) 2005 Elsevier Ltd. All rights reserved.