3-oxo-N-phenylhexanamide | 16682-98-7

• 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: 3-oxo-N-phenylhexanamide
• 英文别名: 3-Oxo-hexansaeure-anilid
• CAS: 16682-98-7
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: NMKOPQKZWILKQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-oxo-N-phenylhexanamide 在 对甲苯磺酰叠氮 、 三乙胺 、 iron(II) chloride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.0h， 生成 N,1-diphenyl-5-propyl-1H-1,2,3-triazole-4-carboxamide
  参考文献：
  名称：

  Intramolecular hydrogen bonding-assisted cyclocondensation of α-diazoketones with various amines: a strategy for highly efficient Wolff 1,2,3-triazole synthesis

  摘要：

  通过利用分子内氢键活化羰基的策略，实现了催化高效Wolff酮内α-重氮酮与芳香胺和脂肪胺的环化缩合反应，成功解决了Wolff型1,2,3-三氮唑合成中缩合效率低下的难题，成为合成高度功能化1,2,3-三氮唑的有力方法。

  DOI：

  10.1039/c2cc33157h
• 作为产物：
  描述：

  N-propylpentan-2-imine 在 盐酸 作用下， 生成 3-oxo-N-phenylhexanamide
  参考文献：
  名称：

  Pocar,D. et al., Gazzetta Chimica Italiana, 1967, vol. 97, p. 597 - 609

  摘要：

  DOI：

文献信息

• Pyrone-3-carboxamide compounds and herbicidal composition thereof
  申请人：Daicel Chemical Industries Ltd.

  公开号：US04886546A1

  公开（公告）日：1989-12-12

  A compound of the formula (I) ##STR1## wherein (1) when R.sub.1 is a C.sub.2-11 alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a lower alkoxyalkyl, an aralkyl which may be substituted, a lower haloalkyl or a 5 or 6 membered heterocycle; R.sub.2, R.sub.3 and R.sub.4 are the same or different, hydrogen, a halogen, cyano, nitro, amino, a lower alkyl, a lower haloalkyl, hydroxy, a lower alkoxy, an aryloxy, carboxy, or a lower alkoxycarbonyl; R.sub.5 is hydrogen, a halogen, a C.sub.1-11 alkyl, an aryl which may be substituted, an aralkyl which may be substituted; R.sub.6 is a C.sub.1-11 alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a lower alkoxyalkyl, an aryl which may be substituted, an aralkyl which may be substituted, a lower haloalkyl, or a 5 or 6 membered heterocycle; or R.sub.5 and R.sub.6 may be combined to form a group of --(CH.sub.2).sub.m -- (m is 3 or 4); (2) when R.sub.1 is an aryl which may be substituted; R.sub.2, R.sub.3, R.sub.4 and R.sub.5 have the same meanings as defined above; R.sub.6 is a C.sub.1-11 alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a lower alkoxyalkyl, an aralkyl which may be substituted, a haloalkyl or a 5 or 6 membered heterocycle, or R.sub.5 and R.sub.6 may be combined to form a group of --(CH.sub.2).sub.m -- (m is 3 or 4); (3) when R.sub.1 is methyl; R.sub.2, R.sub.3, R.sub.4 and R.sub.5 have the same meanings as defined above; R.sub.6 is a C.sub.2-12 alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a lower alkoxyalkyl, an aryl which may be substituted, an aralkyl which may be substituted, a lower haloalkyl or a 5 or 6 membered heterocycle or R.sub.5 and R.sub.6 may be combined to form a group of --(CH.sub.2).sub.m -- (m is 3 or 4); or (4) when R.sub.1 and R.sub.6 are methyl; R.sub.2, R.sub.3 and R.sub.4 have the same meanings as defined above; R.sub.5 is a halogen, a C.sub.1-11 alkyl, an aryl which may be substituted or an aralkyl which may be substituted, which is useful as herbicide.

  式（I）的化合物 ##STR1## 其中（1）当 R.sub.1 是 C.sub.2-11 烷基、较低烯基、较低炔基、环烷基、较低烷氧基烷基、可能被取代的芳基、较低卤代烷基或 5 或 6 成员杂环时；R.sub.2、R.sub.3 和 R.sub.4 相同或不同，氢、卤素、氰基、硝基、氨基、较低烷基、较低卤代烷基、羟基、较低烷氧基、芳氧基、羧基或较低烷氧羰基；R.sub.5 是氢、卤素、C.sub.1-11 烷基、可能被取代的芳基、可能被取代的芳基；R.sub.6 是 C.sub.1-11 烷基、较低烯基、较低炔基、环烷基、较低烷氧基烷基、可能被取代的芳基、可能被取代的芳基、较低卤代烷基或 5 或 6 成员杂环；或 R.sub.5 和 R.sub.6 可以结合形成一个群体 --(CH.sub.2).sub.m --（m 为 3 或 4）；（2）当 R.sub.1 是可能被取代的芳基时；R.sub.2、R.sub.3、R.sub.4 和 R.sub.5 的含义与上述定义相同；R.sub.6 是 C.sub.1-11 烷基、较低烯基、较低炔基、环烷基、较低烷氧基烷基、可能被取代的芳基、卤代烷基或 5 或 6 成员杂环，或 R.sub.5 和 R.sub.6 可以结合形成一个群体 --(CH.sub.2).sub.m --（m 为 3 或 4）；（3）当 R.sub.1 是甲基时；R.sub.2、R.sub.3、R.sub.4 和 R.sub.5 的含义与上述定义相同；R.sub.6 是 C.sub.2-12 烷基、较低烯基、较低炔基、环烷基、较低烷氧基烷基、可能被取代的芳基、可能被取代的芳基、较低卤代烷基或 5 或 6 成员杂环或 R.sub.5 和 R.sub.6 可以结合形成一个群体 --(CH.sub.2).sub.m --（m 为 3 或 4）；或（4）当 R.sub.1 和 R.sub.6 是甲基时；R.sub.2、R.sub.3 和 R.sub.4 的含义与上述定义相同；R.sub.5 是卤素、C.sub.1-11 烷基、可能被取代的芳基或可能被取代的芳基，可用作除草剂。
• Novel crotonanilides
  申请人：Roussel-UCLAF

  公开号：US04014679A1

  公开（公告）日：1977-03-29

  Novel crotonanilides of the formula ##STR1## wherein Z is selected from the group consisting of --O-- and --S--, R is selected from the group consisting of alkyl of 1 to 6 carbon atoms and optionally substituted phenyl, X and Y are individually selected from the group consisting of hydrogen, halogen, lower alkyl of 1 to 6 carbon atoms optionally substituted with at least one halogen, alkoxy of 1 to 3 carbon atoms, alkylthio and alkylsulfinyl of 1 to 6 carbon atoms, acyl of an organic carboxylic acid of 1 to 6 carbon atoms, --NO.sub.2 and --CF.sub.3, R.sub.1 is selected from the group consisting of hydrogen, chlorine, bromine, alkoxycarbonyl with 1 to 6 alkyl carbon atoms, nitro and alkylthio, alkylsulfinyl and alkylsulfonyl of 1 to 3 alkyl carbon atoms and R.sub.2 is alkyl of 1 to 6 carbon atoms, said compounds existing in the form of their E or Z isomers or mixtures thereof and having herbicidal properties.

  具有通式##STR1##的新型巴豆酰苯胺，其中Z选自--O--和--S--，R选自1至6个碳原子的烷基和可任选取代的苯基，X和Y各自选自氢、卤素、1至6个碳原子的低级烷基（可任选至少一个卤素取代）、1至3个碳原子的烷氧基、烷硫基和1至6个碳原子的烷基亚砜、1至6个碳原子的有机羧酸酰基、--NO2和--CF3，R1选自氢、氯、溴、1至6个烷基碳原子的烷氧羰基、硝基、烷硫基、1至3个烷基碳原子的烷基亚砜和烷基磺酰基，R2是1至6个碳原子的烷基，这些化合物以E或Z异构体或其混合物的形式存在，并具有除草活性。
• Lewis Acid Catalyzed Regiospecific Cross-Dehydrative Coupling Reaction of 2-Furylcarbinols with β-Keto Amides or 4-Hydroxycoumarins: A Route to Furyl Enols
  作者：Maozhong Miao、Yi Luo、Hongli Li、Xin Xu、Zhengkai Chen、Jianfeng Xu、Hongjun Ren

  DOI：10.1021/acs.joc.6b00734

  日期：2016.6.17

  Lewis acid-catalyzed directly dehydrative carbon-carbon bond formation reaction of 2-furylcarbinols with beta-keto amides provides a straight method for regioselective synthesis of (Z)-furyl-enols. Moreover, this Lewis acid-catalyzed cross-coupling reaction can be extended to an interesting heterocyclic version, featuring a functionalized 3-furyl-4-hydroxycoumarins synthesis.

  路易斯酸催化的2-呋喃基甲醇与β-酮酰胺的直接脱水碳-碳键形成反应为（Z）-呋喃-烯醇的区域选择性合成提供了一种直接方法。此外，该路易斯酸催化的交叉偶联反应可以扩展为有趣的杂环形式，其特征在于官能化的3-呋喃基-4-羟基香豆素合成。
• Facile and efficient synthesis of quinolin-2(1H)-ones via cyclization of penta-2,4-dienamides mediated by H2SO4
  作者：Xu Liu、Xin Xin、Dexuan Xiang、Rui Zhang、Santosh Kumar、Fenguo Zhou、Dewen Dong

  DOI：10.1039/c2ob25767j

  日期：——

  A facile and efficient synthesis of substituted quinolin-2(1H)-ones is developed via intramolecular cyclization of penta-2,4-dienamides mediated by concentrated H2SO4 (98%), and a mechanism involving the formation of a dicationic superelectrophile, and subsequent intramolecular nucleophilic cyclization reactions is proposed.

  通过浓硫酸（98%）介导的五-2,4-二烯酰胺的分子内环化反应，开发了一种简便且高效的取代喹啉-2(1H)-酮合成方法，并提出了一种涉及双阳离子超级亲电试剂形成和随后的分子内亲核环化反应的机制。
• Asymmetric Robinson-Type Annulation Reaction between β-Ketoamides and α,β-Unsaturated Ketones
  作者：You-ming Huang、Chang-wu Zheng、Gang Zhao

  DOI：10.1021/jo502904n

  日期：2015.4.17

  Enantioselective Robinson-type annulation reaction between β-ketoamide and α,β-unsaturated ketone was developed by utilizing the amino acid derived primary–secondary diamine catalysts. The less reactive acyclic β-ketoamides employed as both electrophile and nucleophile are reported in this asymmetric tandem reaction. A number of chiral cyclohexenone derivatives containing an amide group were obtained

  利用氨基酸衍生的伯-仲二胺催化剂，开发了β-酮酰胺和α，β-不饱和酮之间的对映选择性罗宾逊型环化反应。在该不对称串联反应中报道了用作亲电子试剂和亲核试剂的反应性较低的无环β-酮酰胺。以高收率和良好的选择性获得了许多含有酰胺基的手性环己烯酮衍生物。