3-diethoxyphosphoryl-5-pentyl-2-pyrrolidinone | 838851-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-diethoxyphosphoryl-5-pentyl-2-pyrrolidinone
• 英文别名: 3-diethoxyphosphoryl-5-pentylpyrrolidin-2-one
• CAS: 838851-16-4
• 化学式: C₁₃H₂₆NO₄P
• 分子量: 291.327
• InChiKey: HUSITKINYAJWME-UHFFFAOYSA-N

物化性质

• 沸点：
  442.0±34.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  19.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 3-diethoxyphosphoryl-5-pentyl-2-pyrrolidinone 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 3-Methylene-5-pentyl-pyrrolidin-2-one
  参考文献：
  名称：

  Novel Synthesis, Cytotoxic Evaluation, and Structure−Activity Relationship Studies of a Series of α-Alkylidene-γ-lactones and Lactams

  摘要：

  5-Alkyl- and 5-arylalkyl-3-methylenedihydrofuran-2-ones 13a-e, 3-alkylidenedihydrofuran-2-ones 18a-c, and 3-methylenepyrrolidin-2-ones 16a-e were synthesized utilizing ethyl 2-diethoxyphosphoryl-4-nitroalkanoates 9a-e as common intermediates. All obtained compounds were tested against L-1210, HL-60, and NALM-6 leukemia cells. The highest cytotoxic activity was observed for 3-methylenefuranones 13d,e bearing benzyl or 3,4-dimethoxyphenylmethyl substituents at position 5, with IC50 values of 5.4 and 6.0 mu M, respectively. Contrary to the literature reports, no enhancement in activity due to the presence of a hydroxy group was found when the cytotoxicity of furanones 13a,b,d and 5-(1'-hydroxyalkyl)-3-methylenedihydrofuran-2-ones 6a,b,d was compared. The anticancer activity of pyrrolidinones 16a-e and 3-alkylidenefuranones 18a-c was much weaker than that of furanones 13a-e.

  DOI：

  10.1021/jm048970a
• 作为产物：
  描述：

  1-硝基己烷 在 palladium on activated charcoal 甲酸铵 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.67h， 生成 3-diethoxyphosphoryl-5-pentyl-2-pyrrolidinone
  参考文献：
  名称：

  Novel Synthesis, Cytotoxic Evaluation, and Structure−Activity Relationship Studies of a Series of α-Alkylidene-γ-lactones and Lactams

  摘要：

  5-Alkyl- and 5-arylalkyl-3-methylenedihydrofuran-2-ones 13a-e, 3-alkylidenedihydrofuran-2-ones 18a-c, and 3-methylenepyrrolidin-2-ones 16a-e were synthesized utilizing ethyl 2-diethoxyphosphoryl-4-nitroalkanoates 9a-e as common intermediates. All obtained compounds were tested against L-1210, HL-60, and NALM-6 leukemia cells. The highest cytotoxic activity was observed for 3-methylenefuranones 13d,e bearing benzyl or 3,4-dimethoxyphenylmethyl substituents at position 5, with IC50 values of 5.4 and 6.0 mu M, respectively. Contrary to the literature reports, no enhancement in activity due to the presence of a hydroxy group was found when the cytotoxicity of furanones 13a,b,d and 5-(1'-hydroxyalkyl)-3-methylenedihydrofuran-2-ones 6a,b,d was compared. The anticancer activity of pyrrolidinones 16a-e and 3-alkylidenefuranones 18a-c was much weaker than that of furanones 13a-e.

  DOI：

  10.1021/jm048970a

文献信息

• 2-Diethoxyphosphoryl-4-nitroalkanoates - Versatile Intermediates in the ­Synthesis of α-Alkylidene-γ-lactones and Lactams
  作者：Tomasz Janecki、Edyta Błaszczyk、Henryk Krawczyk

  DOI：10.1055/s-2004-835656

  日期：——

  Michael addition of various nitroalkanes 7a-f to ethyl (2-diethoxyphosphoryl)acrylate (6) gave 2-diethoxyphosphoryl-4-nitroalkanoates 8a-f. Transformation of the nitro functionality into hydroxy or amino group and cyclization yielded 3-(diethoxyphosphoryl)tetrahydro-2-furanones 11a-e or 3-(diethoxyphosphoryl)pyrrolidin-2-ones 14a-e, respectively. These compounds were then used in Horner-Wadsworth-Emmons olefinations of aldehydes to give 3-alkylidenedihydrofuran-2-ones 12a-e or 17a-c and 3-methylidenepyrrolidin-2-ones 15a-e.

  将各种硝基烷烃 7a-f 与(2-二乙氧基磷酰)丙烯酸乙酯 (6) 迈克尔加成，可得到 2-二乙氧基磷酰-4-硝基烷酸酯 8a-f。将硝基官能团转化为羟基或氨基并环化后，分别得到 3-(二乙氧基磷酰)四氢-2-呋喃酮 11a-e 或 3-(二乙氧基磷酰)吡咯烷-2-酮 14a-e。然后将这些化合物用于霍纳-沃兹沃斯-艾蒙斯醛的烯化反应，得到 3-亚烷基二氢呋喃-2-酮 12a-e 或 17a-c，以及 3-亚甲基吡咯烷-2-酮 15a-e。