(E)-N-cyclohexyl-2-phenylethenesulfonamide | 13719-46-5

• 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: (E)-N-cyclohexyl-2-phenylethenesulfonamide
• 英文别名: N-Cyclohexyl-trans-2-phenyl-aethen-1-sulfonamid；N-cyclohexyl-2-phenylethene-1-sulfonamide
• CAS: 13719-46-5
• 化学式: C₁₄H₁₉NO₂S
• 分子量: 265.376
• InChiKey: WXVPPKZGMBAWSS-VAWYXSNFSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  416.8±38.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-cyclohexyl-2-phenylethenesulfonamide 、 3-溴丙烯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Desulfonylation-Initiated Distal Alkenyl Migration in Copper-Catalyzed Alkenylation of Unactivated Alkenes

  摘要：

  A novel and efficient protocol for desulfonylation-initiated distal alkenyl migration and its application to the elusive alkenylation of unactivated alkenes have been presented. This radical cascade process has successfully achieved the vicinal difluoroalkylalkenylation of unactivated alkenes with excellent chemo-, regio-, and stereoselectivity in high efficiency under mild conditions. The reactions afford previously unknown 3,3-difluoro-S-styrylpiperidin-2-one derivatives or beta-styryl-gamma-difluoroalkyl amines bearing a quaternary stereocenter. This is the first report of difunctionalization of unactivated alkenes through desulfonylation-initiated distal alkenyl migration.

  DOI：

  10.1021/acs.orglett.8b02840
• 作为产物：
  描述：

  N-(苯基亚甲基)-环己胺 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 324.5h， 生成 (E)-N-cyclohexyl-2-phenylethenesulfonamide
  参考文献：
  名称：

  Stereospecific C-N Bond Cleavage of 4-Silylated 1,2-Thiazetidine 1,1-Dioxides with EtAlCl2 or AlCl3: Formation of (E)-Vinylsulfonamides.

  摘要：

  将 1，2-噻嗪啶 1，1-二氧化物（β-舒坦类）3 单硅烷化后，可立体选择性地得到 (3R*，4S*)-4-单硅烷-β-舒坦类 4。使用三甲基氯硅烷可以得到二硅烷基化的 β-苏丹酰胺 5。用 EtAlCl2 处理 4-单硅烷基-β-苏丹酰胺 4 时，由于硅基的β阳离子稳定作用，C-N 键发生了立体特异性裂解，从而得到了(E)-乙烯基磺酰胺 (E)-7。(E)-α-硅烷磺酰胺 (E)-7j-l 是在 4，4-二硅烷-β-舒坦 5 与 EtAlCl2 的反应中生成的。4, 4-二硅烷基-β-舒坦与 AlCl3 反应生成 N-脱烷基的 (E)-乙烯基磺酰胺，产率良好。在四丁基氟化铵和 BF3-Et2O 存在下，(E)-α-硅烷基苯乙烯磺酰胺 (E)-10 与苯甲醛反应，得到烯丙基醇 (E)-12。

  DOI：

  10.1248/cpb.46.757

文献信息

• Reactions of 1,2-thiazetidine 1,1-dioxides with organometallics: β-Elimination and NS bond cleavage
  作者：Tetsuo Iwama、Tadashi Kataoka、Osamu Muraoka、Genzoh Tanabe

  DOI：10.1016/s0040-4020(98)00239-7

  日期：1998.5

  Reactions of 4-nonsubstituted β-sultams 1 with methyllithium gave only (E)-vinylsulfonamides2, whereas 2-aminoethyl sulfones 3 were obtained as minor products by use of methylmagnesium bromide. Reactions of 4-monosubstituted β-sultams 6 with organolithiums gave (E)-vinylsulfonamides 7 stereoselectively regardless of the configuration of 3- and 4-substituents. Treatment of 4,4-dimethyl-β-sultam 8a with

  的反应4-未取代的β-磺内酰胺1与甲基仅给出（ë）-vinylsulfonamides 2，而-2氨乙基砜3通过使用甲基溴化镁得到次要产物。的4-单取代反应β-磺内酰胺6与有机锂，得到（É）-vinylsulfonamides 7立体选择性地不论3-和4-取代基的构型。4,4-二甲基β-磺内酰胺的治疗8A用甲基溴化镁和甲基锂提供2-氨基乙基砜9和双砜10，分别和异丙基苯基砜11 通过使用苯基锂或苯基溴化镁获得。
• Solvent-Free Synthesis of Novel Styrenesulfonamide Derivatives and Evaluation of their Antibacterial Activity
  作者：Narjes Khaton Maghsoodi、Tooba Khazaeli、Ahmad Reza Massah

  DOI：10.3184/174751915x14241022318075

  日期：2015.4

  Novel N-aryl-styrenesulfonamide derivatives have been prepared from styrenesulfonyl chloride and a variety of amines under solvent-free conditions and their in vitro anti-bacterial activities against Staphylococcus aureus and Escherichia coli have been determined.

  在无溶剂条件下，以苯乙烯磺酰氯和多种胺为原料制备了新型 N-芳基苯乙烯磺酰胺衍生物，并测定了它们对金黄色葡萄球菌和大肠杆菌的体外抗菌活性。
• Selective CN bond cleavage of 4-silyl-substituted 1,2-thiazetidine 1,1-dioxides with EtAlCl2: Stereospecific formation of (E)-vinylsulfonamides
  作者：Tadashi Kataoka、Tetsuo Iwama、Atsuko Takagi

  DOI：10.1016/0040-4039(96)00269-9

  日期：1996.3

  Monosilylation of 1,2-thiazetidine 1,1-dioxides (β-sultams) furnished β-sultams stereoselectively. Treatment of 4-silylated β-sultams with a Lewis acid caused the selective CN bond cleavage because of the β-silyl stabilization against the resultant carbenium ion followed by desilylation to provide (E)-vinylsulfonamides stereospecifically.

  1,2-噻唑烷1,1-二氧化物（β-杜马酰胺）的单甲硅烷基化立体选择性地提供了β-杜马酚。用路易斯酸处理4-甲硅烷基化的β-sultams导致选择性的CN键断裂，因为β-甲硅烷基对生成的碳正离子具有稳定作用，然后进行甲硅烷基化以立体定向地提供（E）-乙烯基磺酰胺。
• ABRAMOVITCH, R. A.;KRESS, A. O.;PILLAY, K. S.;THOMPSON, W. M., J. ORG. CHEM., 1985, 50, N 12, 2066-2073
  作者：ABRAMOVITCH, R. A.、KRESS, A. O.、PILLAY, K. S.、THOMPSON, W. M.

  DOI：——

  日期：——
• Desulfonylation-Initiated Distal Alkenyl Migration in Copper-Catalyzed Alkenylation of Unactivated Alkenes
  作者：Xiaoyang Wang、Jing Liu、Ze Yu、Minjie Guo、Xiangyang Tang、Guangwei Wang

  DOI：10.1021/acs.orglett.8b02840

  日期：2018.10.19

  A novel and efficient protocol for desulfonylation-initiated distal alkenyl migration and its application to the elusive alkenylation of unactivated alkenes have been presented. This radical cascade process has successfully achieved the vicinal difluoroalkylalkenylation of unactivated alkenes with excellent chemo-, regio-, and stereoselectivity in high efficiency under mild conditions. The reactions afford previously unknown 3,3-difluoro-S-styrylpiperidin-2-one derivatives or beta-styryl-gamma-difluoroalkyl amines bearing a quaternary stereocenter. This is the first report of difunctionalization of unactivated alkenes through desulfonylation-initiated distal alkenyl migration.