N-(1-methyl-2-oxohexyl)benzamide | 191104-37-7

• 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: N-(1-methyl-2-oxohexyl)benzamide
• 英文别名: (+/-)-2-N-benzamido-3-heptanone；N-(3-oxoheptan-2-yl)benzamide
• CAS: 191104-37-7
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: AKLZUNQFVDSZJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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-(1-methyl-2-oxohexyl)benzamide 在 盐酸 、 甲烷磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 28.0h， 生成 17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-2'-methyl-3'-butylpyrrolo[6,7:4',5']morphinan
  参考文献：
  名称：

  Pyrrolomorphinans as δ Opioid Receptor Antagonists. The Role of Steric Hindrance in Conferring Selectivity

  摘要：

  A series of 2',3'-disubstituted pyrrolomorphinans (5a-i) were synthesized to determine the role of steric hindrance at mu and kappa receptors in promoting delta opioid receptor antagonist selectivity. In smooth muscle preparations, five members of the series (5a-c,e,f) possessed K-e values in the range 2-15 nM and were delta selective. Since the unsubstituted analogue 4 possessed delta antagonist potency of similar magnitude, but was not delta selective, it is suggested that the 2',3'-substitution confers delta selectivity by hindering the interaction of the pharmacophore at mu and kappa receptors, while not affecting delta receptors.

  DOI：

  10.1021/jm970189y
• 作为产物：
  描述：

  正丁基锂 、 N-苯甲酰基-DL-丙氨酸 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以52%的产率得到N-(1-methyl-2-oxohexyl)benzamide
  参考文献：
  名称：

  Pyrrolomorphinans as δ Opioid Receptor Antagonists. The Role of Steric Hindrance in Conferring Selectivity

  摘要：

  A series of 2',3'-disubstituted pyrrolomorphinans (5a-i) were synthesized to determine the role of steric hindrance at mu and kappa receptors in promoting delta opioid receptor antagonist selectivity. In smooth muscle preparations, five members of the series (5a-c,e,f) possessed K-e values in the range 2-15 nM and were delta selective. Since the unsubstituted analogue 4 possessed delta antagonist potency of similar magnitude, but was not delta selective, it is suggested that the 2',3'-substitution confers delta selectivity by hindering the interaction of the pharmacophore at mu and kappa receptors, while not affecting delta receptors.

  DOI：

  10.1021/jm970189y

文献信息

• Thionation Using Fluorous Lawesson's Reagent
  作者：Zoltán Kaleta、Brian T. Makowski、Tibor Soós、Roman Dembinski

  DOI：10.1021/ol060208a

  日期：2006.4.1

  [reaction: see text] Thionation of amides, 1,4-diketones, N-(2-oxoalkyl)amides, N,N'-acylhydrazines, and acyl-protected uridines with the use of a fluorous analogue of the Lawesson's reagent leads to thioamides, thiophenes, 1,3-thiazoles, 1,3,4-thiadiazoles, and acyl-protected 4-thiouridines. The isolation of the final products in high yields is achieved in most cases by a simple filtration (fluorous

  [反应：参见正文]使用Lawesson试剂的荧光类似物，酰胺化亚酰胺，1,4-二酮，N-（2-氧代烷基）酰胺，N，N'-酰基肼和酰基保护的尿苷硫代酰胺，噻吩，1,3-噻唑，1,3,4-噻二唑和酰基保护的4-硫代尿苷。在大多数情况下，通过简单的过滤（氟固相萃取）就可以实现高产率的最终产物分离。