N-tosylcyclohex-1-enecarboxamide | 1309657-15-5

• 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: N-tosylcyclohex-1-enecarboxamide
• 英文别名: N-(4-methylphenyl)sulfonylcyclohexene-1-carboxamide
• CAS: 1309657-15-5
• 化学式: C₁₄H₁₇NO₃S
• 分子量: 279.36
• InChiKey: XETGZGSZLLAMSY-UHFFFAOYSA-N

物化性质

• 熔点：
  164-166 °C
• 密度：
  1.248±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-tosylcyclohex-1-enecarboxamide 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 sodium acetate 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Rhodium(III)-Catalyzed Olefinic C–H Alkynylation of Acrylamides Using Tosyl-Imide as Directing Group

  摘要：

  The Rh(III)-catalyzed CH alkynylation of acrylamide derivative is realized using a hypervalent alkynyl iodine reagent. The use of a weakly coordinating directing group proved to be of critical importance. This reaction displays broad functional group tolerance and high efficiency, which opens a new synthetic pathway to access functionalized 1,3-enyne skeletons.

  DOI：

  10.1021/ol502984g
• 作为产物：
  描述：

  1-cyclohexene-1-carboxaldehyde 、 [(N-tosylimino)iodo]benzene 在 吡啶 、 iron(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以60%的产率得到N-tosylcyclohex-1-enecarboxamide
  参考文献：
  名称：

  Iron(II)-Catalyzed Amidation of Aldehydes with Iminoiodinanes at Room Temperature and under Microwave-Assisted Conditions

  摘要：

  A method for the amidation of aldehydes with PhI=NTs/PhI=NNs as the nitrogen source and an inexpensive iron(II) chloride + pyridine as the in situ formed precatalyst under mild conditions at room temperature or microwave assisted conditions is described. The reaction was operationally straightforward and accomplished in moderate to excellent product yields (20-99%) and with complete chemoselectivity with the new C-N bond forming only at the formylic C-H bond in substrates containing other reactive functional groups. By utilizing microwave irradiation, comparable product yields and short reaction times of 1 h could be accomplished. The mechanism is suggested to involve insertion of a putative iron-nitrene/imido group to the formylic C H bond of the substrate via a H-atom abstraction/radical rebound pathway mediated by the precatalyst [Fe(py)(4)Cl-2] generated in situ from reaction of FeCl2 with pyridine.

  DOI：

  10.1021/jo200284a

文献信息

• Rhodium(<scp>iii</scp>)-catalyzed C–H allylation of electron-deficient alkenes with allyl acetates
  作者：Chao Feng、Daming Feng、Teck-Peng Loh

  DOI：10.1039/c4cc07597h

  日期：——

  Rhodium-catalyzed C–H allylation of acrylamide derivatives with various allyl acetates was reported. The use of weakly coordinating directing group resulted in high reaction efficiency and excellent γ-selectivity. This reaction displays broad functional group tolerance, which opens a new synthetic pathway for the access of functionalized 1,4-diene skeletons.

  铑催化的C-H烯丙基化反应报道了使用各种烯丙醋酸酯对丙烯酰胺衍生物进行反应。使用弱配位导向基团导致高反应效率和优异的γ-选择性。该反应显示出广泛的官能团容忍性，为获得官能化的1,4-二烯骨架开辟了新的合成途径。
• Iridium-catalyzed alkenyl C–H allylation using conjugated dienes
  作者：Liangyao Xu、Keke Meng、Jian Zhang、Yaling Sun、Xiunan Lu、Tingyan Li、Yan Jiang、Guofu Zhong

  DOI：10.1039/c9cc04419a

  日期：——

  An iridium-catalyzed C–H allylation of acrylamides with conjugated dienes was developed, using NH-Ts amide as the directing group. The ligand- and additive-free protocol provided a convenient and atom economic synthesis of branched 1,4-diene skeletons, enabling the tolerance of a wide scope of functionalities such as OMe, F, Cl, Br and CF3. The utility of this protocol is also demonstrated by a preparative

  以NH-Ts酰胺为指导基团，开发了铱与共轭二烯催化的CHH丙烯酰胺化反应。不含配体和无添加剂的协议为分支的1,4-二烯骨架提供了方便且原子经济的合成方法，从而能够耐受诸如OMe，F，Cl，Br和CF 3之类的广泛功能。该协议的实用性还通过制备规模以及青蒿酰胺的C–H功能化得到了证明。此外，通过甲基化和水解程序有效地除去了NH-Ts酰胺，以提供1，4-二烯酸。
• Iridium-catalyzed Annulation of α,β-Unsaturated Amides with Electron-deficient Conjugated Dienes
  作者：Kotone Murakami、Midori Nagamoto、Takahiro Nishimura

  DOI：10.1246/cl.200193

  日期：2020.6.5

  Annulation of α,β-unsaturated amides with electron-deficient 1,3-dienes gave 5,6-dihydropyridin-2(1H)-ones in the presence of a hydroxoiridium catalyst. The reaction proceeded via direct C–H alkyla...

  在羟基铱催化剂存在下，α,β-不饱和酰胺与缺电子的 1,3-二烯环化得到 5,6-二氢吡啶-2(1H)-酮。反应通过直接的C-H烷基化进行...
• Highly Regioselective Rh^III-Catalyzed Thiolation of <i>N</i>-Tosyl Acrylamides: General Access to (<i>Z</i>)-β-Alkenyl Sulfides
  作者：Can Liu、Yi Fang、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1021/acs.orglett.8b02552

  日期：2018.10.5

  with good tolerance of functional groups. Turnover numbers (TONs) of up to 7100 were obtained utilizing 0.01 mol % RhIII catalyst. In addition, diphenyl diselenide was also successfully applied to this reaction for the construction of (Z)-β-alkenyl selenides under identical conditions.

  已经开发出具有易于获得的二硫化物的区域选择性铑催化的N-甲苯磺酰基丙烯酰胺的硫醇化。通过N-甲苯磺酰胺辅助的链烯基C（sp 2）-H键的活化，以中等至极好的收率构建了一系列（Z）-链烯基硫化物，并对官能团具有良好的耐受性。使用0.01 mol％Rh III催化剂可获得高达7100的周转率（TONs）。另外，二苯基二硒化物也成功地用于该反应，以在相同条件下构建（Z）-β-链烯基硒化物。
• Palladium-Catalyzed [4+2] Annulation of Aryl and Alkenyl Carboxamides with 1,3-Dienes via C–H Functionalization: Synthesis of 3,4-Dihydroisoquinolones and 5,6-Dihydropyridinones
  作者：Manman Sun、Jinshan Li、Weida Chen、Haijian Wu、Jianguo Yang、Zhiming Wang

  DOI：10.1055/s-0039-1690219

  日期：2020.4

  Palladium-catalyzed [4+2] annulation of aryl and alkenyl carboxamides with 1,3-dienes via C–H functionalization is developed using air as the terminal oxidant. The method demonstrates good functional group tolerance and high stereoselectivity, affording a series of 3,4-dihydroisoquinolones and 5,6-dihydropyridinones in yields of up to 99%. Palladium-catalyzed [4+2] annulation of aryl and alkenyl carboxamides

  抽象的 使用空气作为末端氧化剂，开发了钯通过C–H功能化与1，3-二烯催化的[4 + 2]芳基和烯基羧酰胺环化反应。该方法显示出良好的官能团耐受性和高立体选择性，提供了一系列3,4-二氢异喹诺酮和5,6-二氢吡啶酮，收率高达99％。 使用空气作为末端氧化剂，开发了钯通过C–H功能化与1，3-二烯催化的[4 + 2]芳基和烯基羧酰胺环化反应。该方法显示出良好的官能团耐受性和高立体选择性，提供了一系列3,4-二氢异喹诺酮和5,6-二氢吡啶酮，收率高达99％。