N-(4-oxo-4-phenylbutan-2-yl)benzamide | 259824-07-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-oxo-4-phenylbutan-2-yl)benzamide
• CAS: 259824-07-2
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: DZZCTCOQUCQXKY-UHFFFAOYSA-N

物化性质

• 沸点：
  492.7±28.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-oxo-4-phenylbutan-2-yl)benzamide 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 4-methyl-2,6-diphenyl-4H-1,3-thiazine
  参考文献：
  名称：

  Ori, Mayuko; Nishio, Takehiko, Heterocycles, 2000, vol. 52, # 1, p. 111 - 116

  摘要：

  DOI：
• 作为产物：
  描述：

  N-乙酰基-苯甲酰胺 在 3-(1-piperidino)propyl functionalized silica gel (SiO₂-Pip) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-(4-oxo-4-phenylbutan-2-yl)benzamide
  参考文献：
  名称：

  1-（N-酰基氨基）烷基三苯基phosph盐与甲硅烷基烯醇盐的无催化剂曼尼希型反应

  摘要：

  开发了四氟硼酸1-（N-酰基氨基）烷基三苯基phosph与烯丙基甲硅烷基酯的无催化剂反应，以制备β-氨基羰基化合物。所报道的方法是用于制备N-保护的β-氨基酯以及N-保护的β-氨基酮的有用方法。起始的1-（N-酰基氨基）烷基三苯基phosph四氟硼酸酯可容易地从N-保护的α-氨基酸获得。因此，提出的方法可以被认为是一种新的方法，用于N-保护的α-氨基酸的α-同源制备β-氨基酸衍生物。

  DOI：

  10.1016/j.tet.2018.12.042

文献信息

• Efficient Brønsted acid-catalyzed aza-Michael reaction of amides and ureas with α,β-unsaturated enones under high-pressure conditions
  作者：Saleha Azad、Tomohiro Kobayashi、Keiji Nakano、Yoshiyasu Ichikawa、Hiyoshizo Kotsuki

  DOI：10.1016/j.tetlet.2008.10.082

  日期：2009.1

  A new strategy for the aza-Michael reaction of amides and ureas with α,β-unsaturated enones, which uses p-TsOH·H2O as an efficient and inexpensive catalyst under high-pressure conditions, has been developed.

  开发了一种新的策略，用于酰胺和脲与α，β-不饱和烯酮的aza-Michael反应，该方法在高压条件下使用p -TsOH·H 2 O作为一种高效且廉价的催化剂。
• Palladium-Catalyzed Hydroamidation Reaction of Enones
  作者：Kiyosei Takasu、Masataka Ihara、Naoko Nishida

  DOI：10.1055/s-2004-830852

  日期：——

  A catalytic amount of Pd(PhCN)2Cl2 promotes conjugate addition reaction of amides with enones to afford β-amidoketones (aza-Michael reaction, hydroamidation reaction) under solvent-free conditions. The produced β-amidoketones could be transformed into multi-substituted piperidinones.

  在无溶剂条件下，催化量的 Pd(PhCN)2Cl2 可促进酰胺与烯酮的共轭加成反应，生成 δ-氨基酮（氮杂迈克尔反应、加氢酰胺化反应）。生成的δ-氨基酮可转化为多取代的哌啶酮。
• Nickel‐Catalyzed Site‐Selective Intermolecular C(sp ³ )−H Amidation
  作者：Jinhong Chen、Hao Wang、Craig S. Day、Ruben Martin

  DOI：10.1002/anie.202212983

  日期：2022.12.12

  A Ni-catalyzed site-selective intermolecular C(sp3)−H amidation has been developed. This protocol is characterized by its mild conditions, broad substrate scope, and excellent chemo- and site-selectivity, thus unlocking a complementary technique to conventional C(sp3)−N bond-forming reactions for accessing amine architectures from simple building blocks.

  已开发出镍催化的位点选择性分子间 C(sp 3 )−H 酰胺化反应。该协议的特点是条件温和、底物范围广以及出色的化学和位点选择性，从而解锁了传统 C(sp 3 ) −N键形成反应的互补技术，用于从简单的构建块访问胺结构。
• Catalytic Conjugate Additions of Nitrogen-, Phosphorus-, and Carbon-Containing Nucleophiles by Amphoteric Vanadyl Triflate
  作者：Yow-Dzer Lin、Jun-Qi Kao、Chien-Tien Chen

  DOI：10.1021/ol702302y

  日期：2007.12.1

  A series of carbamates, amides, N-tosyl amides, (hetero)arenes, and hydrogen phosphines/phosphites has been examined as nucleophiles for (hetero)Michael-type additions to enones and enamides catalyzed by amphoteric vanadyl triflate under mild and neutral conditions. The newly developed C-N, C-P, and C-C bond-formation protocols were carried out smoothly in good to high yields without intervention of any 1,2-additions.
• Thionation ofω-Acylamino Ketones withLawesson's Reagent: Convenient Synthesis of 1,3-Thiazoles and 4H-1,3-Thiazines
  作者：Takehiko Nishio、Mayuko Ori

  DOI：10.1002/1522-2675(20010815)84:8<2347::aid-hlca2347>3.0.co;2-n

  日期：2001.8.15

  The reaction of omega -acylamino ketones with Lawesson's reagent (=2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide; LR) is described. Treatment of 2-acylamino ketones 1 (n = 0) with LR gave 1,3-thiazole derivatives 3 in good yields (Scheme I and Table 1). The 4H-1,3-thiazines 4 were obtained as main products by treatment of 3-acylamino ketones 2 (n = 1) with an equimolar amount of LR, while mainly the corresponding 3-(thioacyl)amino ketones 5 were isolated when 0.5 equiv. of LR was used. The 3-acylamino esters 7 also reacted with LR to give the corresponding 3-(thioacyl)amino esters 8 (Scheme 3 and Table 2).