(E)-2-(Diethoxy-phosphoryl)-3-naphthalen-1-yl-acrylic acid ethyl ester | 13507-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-2-(Diethoxy-phosphoryl)-3-naphthalen-1-yl-acrylic acid ethyl ester
• 英文别名: Ethyl 2-(diethoxyphosphoryl)-3-(naphthalen-1-yl)acrylate；ethyl (E)-2-diethoxyphosphoryl-3-naphthalen-1-ylprop-2-enoate
• CAS: 13507-51-2
• 化学式: C₁₉H₂₃O₅P
• 分子量: 362.362
• InChiKey: UXIVPFUAIKXJLT-NBVRZTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-2-(Diethoxy-phosphoryl)-3-naphthalen-1-yl-acrylic acid ethyl ester 在 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 26.5h， 生成 ethyl 2-(tert-butoxycarbonylamino-1-naphthylmethyl)acrylate
  参考文献：
  名称：

  New, Simple and Versatile Synthesis of Protected α-Alkylidene-β-amino Acids from Activated Vinylphosphonates

  摘要：

  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。

  DOI：

  10.1055/s-2006-944184

文献信息

• 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.