1-(3,3-dimethyl-2-oxobutyl)pyridin-2(1H)-one | 108664-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(3,3-dimethyl-2-oxobutyl)pyridin-2(1H)-one
• 英文别名: 1-(3,3-Dimethyl-2-oxobutyl)pyridin-2-one
• CAS: 108664-65-9
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: OUEGSANULHOPBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  四甲基甲烷二胺 、 1-(3,3-dimethyl-2-oxobutyl)pyridin-2(1H)-one 在 乙酸酐 作用下， 反应 0.25h， 生成 1-(3,3-Dimethyl-1-methylene-2-oxo-butyl)-1H-pyridin-2-one
  参考文献：
  名称：

  Synthesis and antifungal activity of a series of novel 1,2-disubstituted propenones

  摘要：

  To find an antifungal agent other than those of the imidazole and triazole series, a new class of 1,2-disubstituted propenones I and II was prepared and tested for antifungal activity. Comparison of the structure-activity relationships showed that the conjugated structure of carbonyl and exomethylene groups in I and II plays an important role in potent antifungal activity. However, it is noteworthy that compounds 53, 54, and 56, which have a hydroxymethyl or methoxymethyl group instead of an exo-methylene group in I, also showed potent activity. Although many compounds exhibited strong antifungal activity in vitro, none showed activity in vivo of oral efficacy against subacute systemic candidiasis in mice.

  DOI：

  10.1021/jm00391a037
• 作为产物：
  描述：

  3-羟基吡啶 、 1-(dimethyl(oxo)-λ⁶-sulfanylidene)-3,3-dimethylbutan-2-one 在 五甲基环戊二烯基双(三苯基膦)氯化钌(II) 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以93%的产率得到1-(3,3-dimethyl-2-oxobutyl)pyridin-2(1H)-one
  参考文献：
  名称：

  钌催化的2-吡啶酮/ 7-氮杂吲哚与亚砜鎓叶立德的化学选择性NH键插入反应

  摘要：

  已经开发了钌催化的2-吡啶酮的高化学选择性N-烷基化，以良好的产率和优异的N-选择性提供了N-烷基化的2-吡啶酮衍生物。实现这种空前的N–H而不是O–H插入反应的关键是使用CpRu（PPh 3）2 Cl作为催化剂，使用亚砜基烷基化物作为烷基化试剂。此外，通过稍微改变反应条件，该方案也适用于7-氮杂吲哚。此外，yl化钠也是合适的烷基化试剂，以良好的选择性提供N-烷基化的2-吡啶酮。

  DOI：

  10.1021/acs.orglett.0c04229

文献信息

• OGATA, MASARU;MATSUMOTO, HIROSHI;KIDA, SHIRO;SHIMIZU, SUMIO;TAWARA, KATSU+, J. MED. CHEM., 30,(1987) N 8, 1497-1502
  作者：OGATA, MASARU、MATSUMOTO, HIROSHI、KIDA, SHIRO、SHIMIZU, SUMIO、TAWARA, KATSU+

  DOI：——

  日期：——
• Synthesis and antifungal activity of a series of novel 1,2-disubstituted propenones
  作者：Masaru Ogata、Hiroshi Matsumoto、Shiro Kida、Sumio Shimizu、Katsuya Tawara、Yoshimi Kawamura

  DOI：10.1021/jm00391a037

  日期：1987.8

  To find an antifungal agent other than those of the imidazole and triazole series, a new class of 1,2-disubstituted propenones I and II was prepared and tested for antifungal activity. Comparison of the structure-activity relationships showed that the conjugated structure of carbonyl and exomethylene groups in I and II plays an important role in potent antifungal activity. However, it is noteworthy that compounds 53, 54, and 56, which have a hydroxymethyl or methoxymethyl group instead of an exo-methylene group in I, also showed potent activity. Although many compounds exhibited strong antifungal activity in vitro, none showed activity in vivo of oral efficacy against subacute systemic candidiasis in mice.
• Ruthenium-Catalyzed Chemoselective N–H Bond Insertion Reactions of 2-Pyridones/7-Azaindoles with Sulfoxonium Ylides
  作者：Xiaofeng Liu、Ying Shao、Jiangtao Sun

  DOI：10.1021/acs.orglett.0c04229

  日期：2021.2.5

  excellent N-selectivity. The key to achieve this unprecedented N–H rather than O–H insertion reaction is the use of CpRu(PPh3)2Cl as the catalyst and sulfoxonium ylides as the alkylation reagents. Moreover, this protocol is also amenable to 7-azaindoles by slightly varying the reaction conditions. Furthermore, sulfonium ylides are also suitable alkylation reagents, providing the N-alkylated 2-pyridones in

  已经开发了钌催化的2-吡啶酮的高化学选择性N-烷基化，以良好的产率和优异的N-选择性提供了N-烷基化的2-吡啶酮衍生物。实现这种空前的N–H而不是O–H插入反应的关键是使用CpRu（PPh 3）2 Cl作为催化剂，使用亚砜基烷基化物作为烷基化试剂。此外，通过稍微改变反应条件，该方案也适用于7-氮杂吲哚。此外，yl化钠也是合适的烷基化试剂，以良好的选择性提供N-烷基化的2-吡啶酮。