(E)-Ethyl 2-diethoxyphosphoryl-4-methyl-2-heptenoate | 283169-57-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-Ethyl 2-diethoxyphosphoryl-4-methyl-2-heptenoate
• 英文别名: ethyl (E)-2-diethoxyphosphoryl-4-methyl-2-heptenoate
• CAS: 283169-57-3
• 化学式: C₁₄H₂₇O₅P
• 分子量: 306.339
• InChiKey: TVCIWEIQEJLZPH-ACCUITESSA-N

物化性质

• 沸点：
  382.9±34.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  20.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-Ethyl 2-diethoxyphosphoryl-4-methyl-2-heptenoate 在 potassium carbonate 、 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 20.75h， 生成 2-methyl-3-(1-methyl-butyl)-4-methylene-isoxazolidin-5-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 4-methylideneisoxazolidin-5-ones – A new class of highly cytotoxic α-methylidene-γ-lactones

  摘要：

  Two 4-methylideneisoxazolidin-5-ones (4a,b), which are alpha-methylidene-gamma-lactones containing a nitrogen atom in the lactone ring, were synthesized. Their cytotoxic properties were evaluated against promyelocytic leukemia HL-60 cells. Both 4a and 4b exhibited relatively high cytotoxic activity with an IC50 of 4.1 and 5.4 mu M, respectively. Caspase-3 activity assay revealed that both isoxazolidinones (4) were able to induce apoptosis process in time- and concentration-dependent manner. Using multiplex PCR analysis, it was observed that 4 caused distinct inhibition of BCL-2 gene expression. Expression of BAX, a pro-apoptotic gene remained unchanged. It was also found that 4a,b did not induce the expression of MDR] and MRP1 genes, related to multidrug resistance. In addition, cytotoxicity data obtained for drug-sensitive and drug-resistant HL60 ADR cells revealed that the investigated compounds were poor substrates for transport by MRP1 efflux pump, suggesting that they might be useful for treating drug-resistant tumors. Furthermore, antimicrobial properties of 4a,b were evaluated. They showed significant activity against fungi Candida albicans, but only a weak activity against all tested Gram-positive and Gram-negative bacterial strains. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.09.005
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 2-甲基戊醛 在 哌啶 、 溶剂黄146 作用下， 反应 15.0h， 生成 (Z)-Ethyl 2-diethoxyphosphoryl-4-methyl-2-heptenoate 、 (E)-Ethyl 2-diethoxyphosphoryl-4-methyl-2-heptenoate
  参考文献：
  名称：

  Janecki, Tomasz; Kuś, Andrzej; Krawczyk, Henryk, Synlett, 2000, # 5, p. 611 - 614

  摘要：

  DOI：

文献信息

• New, Simple and Versatile Synthesis of Protected α-Alkylidene-β-amino Acids from Activated Vinylphosphonates
  作者：Tomasz Janecki、Tomasz Wąsek、Jacek Olczak

  DOI：10.1055/s-2006-944184

  日期：2006.6

  A two-step route to Boc-protected α-alkylidene-β-amino esters was developed by addition of sodium tert-butylcarbamate to ethyl 2-diethoxyphosphoryl-2-alkenoates followed by the Horner-Wadsworth-Emmons olefination of aldehydes using intermediate 2-diethoxyphosphoryl-3-tert-butoxycarbonylaminoalkanoates.

  通过将叔丁基氨基甲酸钠加到 2-二乙氧基磷酰-2-烯酸乙酯中，然后使用 2-二乙氧基磷酰-3-叔丁氧羰基氨基烷酸乙酯中间体进行醛的霍纳-沃兹沃斯-埃蒙斯烯化反应，开发出了一条分两步制备 Boc 保护的δ-亚烷基δ-氨基酯的路线。
• 4-Methylideneisoxazolidin-5-ones—A new class of α-methylidene-γ-lactones with high cytostatic activity
  作者：Tomasz Janecki、Tomasz Wąsek、Marek Różalski、Urszula Krajewska、Kazimierz Studzian、Anna Janecka

  DOI：10.1016/j.bmcl.2005.11.032

  日期：2006.3

  A novel, general method of synthesis of 4-methylideneisoxazolidin-5-ones 10 is described. The target compounds were synthesized starting from ethyl 2-diethoxyphosphoryl-2-alkenoates 6 or dicyclohexylammonium 4-diethoxyphosphoryl-2-alkenoates 7. Addition of N-methylhydroxylamine hydrochloride to these Michael acceptors, lactonization to 4-diethoxyphosphorylisoxazolidin-5-ones 9, and Horner-Wadsworth-Emmons olefination of formaldehyde using 9 gave the title isoxazolidinones 10. All obtained compounds were tested against L-1210, HL-60, and NALM-6 leukemia cell lines. Several isoxazolidinones 10 were found to be very potent with IC50 < 1 mu M. The highest cytostatic activity against HL-60 was observed for 10a and against NALM-6 for 10b with IC50 values of 0.74 and 0.34 mu M, respectively. (C) 2005 Elsevier Ltd. All rights reserved.