tert-butyl 2-diethoxyphosphoryl-3-isopropyl-5-oxohexanoate | 1215035-13-4

• 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: tert-butyl 2-diethoxyphosphoryl-3-isopropyl-5-oxohexanoate
• 英文别名: Tert-butyl 2-diethoxyphosphoryl-5-oxo-3-propan-2-ylhexanoate
• CAS: 1215035-13-4
• 化学式: C₁₇H₃₃O₆P
• 分子量: 364.419
• InChiKey: MTJXZQXROYOJSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-diethoxyphosphoryl-3-isopropyl-5-oxohexanoate 在 二异丁基氢化铝 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 Tert-butyl 2-diethoxyphosphoryl-5-hydroxy-3-propan-2-ylhexanoate
  参考文献：
  名称：

  Synthesis and cytotoxic evaluation of β-alkyl or β-aryl-δ-methyl-α-methylene-δ-lactones. Comparison with the corresponding γ-lactones

  摘要：

  We present a simple and general strategy for the synthesis of beta,delta-disubstituted-alpha-methylene-delta-lactones starting from easily available tert-butyl 2-(diethoxyphosphoryl)alk-2-enoates. The elaborated synthetic protocol includes pyrrolidine-catalyzed Michael addition of acetone, diastereoselective reduction of the carbonyl group, lactonization and finally the Horner-Wadsworth-Emmons reaction with formaldehyde. All alpha-methylene-delta-lactones were evaluated in vitro against mouse leukemia cell line L-1210 and two human leukemia cell lines HL-60 and NALM-6. Comparison of cytotoxic activity with corresponding alpha-methylene-gamma-lactones is also discussed. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.018
• 作为产物：
  描述：

  、 丙酮 在 四氢吡咯 作用下， 反应 264.0h， 以89%的产率得到tert-butyl 2-diethoxyphosphoryl-3-isopropyl-5-oxohexanoate
  参考文献：
  名称：

  Synthesis and cytotoxic evaluation of β-alkyl or β-aryl-δ-methyl-α-methylene-δ-lactones. Comparison with the corresponding γ-lactones

  摘要：

  We present a simple and general strategy for the synthesis of beta,delta-disubstituted-alpha-methylene-delta-lactones starting from easily available tert-butyl 2-(diethoxyphosphoryl)alk-2-enoates. The elaborated synthetic protocol includes pyrrolidine-catalyzed Michael addition of acetone, diastereoselective reduction of the carbonyl group, lactonization and finally the Horner-Wadsworth-Emmons reaction with formaldehyde. All alpha-methylene-delta-lactones were evaluated in vitro against mouse leukemia cell line L-1210 and two human leukemia cell lines HL-60 and NALM-6. Comparison of cytotoxic activity with corresponding alpha-methylene-gamma-lactones is also discussed. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.018

文献信息

• Synthesis and cytotoxic evaluation of β-alkyl or β-aryl-δ-methyl-α-methylene-δ-lactones. Comparison with the corresponding γ-lactones
  作者：Łukasz Albrecht、Jakub Wojciechowski、Anna Albrecht、Wojciech M. Wolf、Anna Janecka、Kazimierz Studzian、Urszula Krajewska、Marek Różalski、Tomasz Janecki、Henryk Krawczyk

  DOI：10.1016/j.ejmech.2009.11.018

  日期：2010.2

  We present a simple and general strategy for the synthesis of beta,delta-disubstituted-alpha-methylene-delta-lactones starting from easily available tert-butyl 2-(diethoxyphosphoryl)alk-2-enoates. The elaborated synthetic protocol includes pyrrolidine-catalyzed Michael addition of acetone, diastereoselective reduction of the carbonyl group, lactonization and finally the Horner-Wadsworth-Emmons reaction with formaldehyde. All alpha-methylene-delta-lactones were evaluated in vitro against mouse leukemia cell line L-1210 and two human leukemia cell lines HL-60 and NALM-6. Comparison of cytotoxic activity with corresponding alpha-methylene-gamma-lactones is also discussed. (C) 2009 Elsevier Masson SAS. All rights reserved.