N,N-dimethyl-3-oxo-3-phenylpropanamide | 18871-71-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N-dimethyl-3-oxo-3-phenylpropanamide
• 英文别名: N,N-Dimethylbenzoylacetamide
• CAS: 18871-71-1
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: UQYBNEDJDMXSKH-UHFFFAOYSA-N

物化性质

• 熔点：
  84.5-85 °C
• 沸点：
  333.1±25.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-3-oxo-3-phenylpropanamide 在 劳森试剂 、 silica gel 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.17h， 生成 (R)-N-(1-(4-benzoyl-5-(dimethylamino)thiophen-2-yl)heptyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Optically Active Thiophenes via an Organocatalytic One-Pot Methodology

  摘要：

  A general methodology for the synthesis of trisubstituted, optically active thiophenes by an organocatalytic one-pot reaction cascade is presented. The target products are synthesized in good yields (up to 92%) and with excellent enantioselectivities (up to 98% ee). Importantly, based on practical and easily available starting materials, the presented methodology can be conducted under mild reaction conditions. To further elucidate the generality, the synthesis of optically active thienoindoles, as well as selenophenes, is also demonstrated.

  DOI：

  10.1021/ol203237r
• 作为产物：
  描述：

  NN-dimethyl-2-benzoyl-4-methylvaleramide 以 甲醇 为溶剂， 以100%的产率得到N,N-dimethyl-3-oxo-3-phenylpropanamide
  参考文献：
  名称：

  Hasegawa, Tadashi; Arata, Yoshiaki; Mizuno, Kouichi, Journal of the Chemical Society. Perkin transactions I, 1986, p. 541 - 544

  摘要：

  DOI：

文献信息

• Direct access to α-sulfenylated amides/esters <i>via</i> sequential oxidative sulfenylation and C–C bond cleavage of 3-oxobutyric amides/esters
  作者：Yi Jiang、Jie-dan Deng、Hui-hong Wang、Jiao-xia Zou、Yong-qiang Wang、Jin-hong Chen、Long-qing Zhu、Hong-hua Zhang、Xue Peng、Zhen Wang

  DOI：10.1039/c7cc09026a

  日期：——

  An efficient, environmentally benign and unprecedented synthesis of various α-sulfenylated amides/esters has been developed under oxygen atmosphere. The reaction shows good functional group tolerance and excellent chemo/regioselectivity. All the desired products were obtained in moderate to excellent yields, even on the gram scale. Practically, the related α-thiol Weinreb amide can be readily transferred

  在氧气气氛下，已经开发出一种高效，环境友好的和前所未有的合成各种α-亚磺酰化酰胺/酯的方法。该反应显示出良好的官能团耐受性和优异的化学/区域选择性。即使在克规模上，也以中等至极好的收率获得了所有所需的产品。实际上，相关的α-硫醇Weinreb酰胺可以很容易地转移到一系列预期的化合物中，并且硒原子可以高产率地引入到酰胺的α-位。
• SO₂F₂-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes
  作者：Gao-Feng Zha、Wan-Yin Fang、You-Gui Li、Jing Leng、Xing Chen、Hua-Li Qin

  DOI：10.1021/jacs.8b10069

  日期：2018.12.19

  Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C≡C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes

  通过 SO2F2 促进的脱水和脱氢过程，以高产率（超过 40 个实例，高达 95% 的产率）实现了从廉价、丰富的醇直接合成炔烃。sp3-sp3 (CC) 键向 sp-sp (C≡C) 键的这种直接转变只需要在温和条件下廉价且容易获得的试剂（无过渡金属）。粗炔烃足够不含杂质，可以直接用于进一步的转化，如区域选择性 Huisgen 炔烃 - 叠氮化物与 PhN3 环加成反应所示，得到 1,4-取代的 1,2,3-四唑（16 个例子，高达 92%产率）和 Sonogashira 偶联（10 个例子，产率高达 77%）。
• Efficient electrophilic fluorination of β-dicarbonyl compounds with the selectfluor reagent F-TEDA-BF₄{1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)}
  作者：R. Eric Banks、Nicholas J. Lawrence、Allan L. Popplewell

  DOI：10.1039/c39940000343

  日期：——

  1,3-Dicarbonyl compounds (acyclic and cyclic 1,3-diketones, β-ketoesters, β-ketoamides) are converted efficiently to 2-monofluoro derivatives, and thence to 2,2-difluoro derivatives, with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate).

  1,3-二羰基化合物（包括无环和环状1,3-二酮、β-酮酯、β-酮酰胺）能够高效转化为2-单氟衍生物，进而通过1-氯甲基-4-氟-1,4-二氮杂双环[2.2.2]辛烷双(四氟硼酸盐)转化为2,2-二氟衍生物。
• The Employment of Sodium Hydride as a Michael Donor in Palladium‐catalyzed Reductions of α, β‐Unsaturated Carbonyl Compounds
  作者：Ye Liu、Yujian Mao、Yanwei Hu、Jingjing Gui、Liang Wang、Wei Wang、Shilei Zhang

  DOI：10.1002/adsc.201801676

  日期：2019.4

  Sodium hydride was employed as a Michael donor under the catalysis of PdCl2 for 1,4‐conjugate reductions of α, β‐unsaturated carbonyl compounds, which features operational simplicity, mild conditions and high atom‐economy. The merits of NaH as a reductant were demonstrated by the one‐pot or cascade reactions for the syntheses of complex molecules.

  在PdCl 2催化下，氢化钠被用作Michael供体，以减少α，β-不饱和羰基化合物的1,4-共轭还原，其具有操作简便，条件温和和高原子经济性的特点。NaH作为还原剂的优点通过合成复杂分子的一锅法或级联反应得到了证明。
• Microwave-assisted rapid electrophilic fluorination of 1,3-dicarbonyl derivatives with Selectfluor®
  作者：Ji-Chang Xiao、Jean’ne M. Shreeve

  DOI：10.1016/j.jfluchem.2004.10.043

  日期：2005.4

  A microwave-assisted fluorination method for 1,3-dicarbonyl compounds using Selectfluor® has been developed. 2-Monofluorinated products can be obtained in high yield in neutral reaction conditions with addition of 1 eq. of Selectfluor®. Treatment of 1,3-dicarbonyls with 3 eq. of Selectfluor® in the presence of tetrabutylammonium hydroxide (TBAH) as the base results in the formation of 2,2-difluorinated

  用于使用的Selectfluor 1,3-二羰基化合物的微波辅助的氟化方法®已经研制成功。加入1eq。的2-单氟化产物可以在中性反应条件下高收率地获得。的Selectfluor的®。用3eq。处理1，3-二羰基。的的Selectfluor ®在氢氧化四丁基铵（TBAH）的存在下，在仅2,2-二氟化衍生物的形成基部的结果。