muricatacinone ou (4S)-5-oxo-heptadecan-4-olide | 139396-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: muricatacinone ou (4S)-5-oxo-heptadecan-4-olide
• 英文别名: (5S)-5-tridecanoyloxolan-2-one
• CAS: 139396-44-4
• 化学式: C₁₇H₃₀O₃
• 分子量: 282.423
• InChiKey: AJINPLAFMGAAHB-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  muricatacinone ou (4S)-5-oxo-heptadecan-4-olide 在 咪唑 、 三正丁基氢锡 、 silica gel 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 72.25h， 生成 (1SR,4S,5S)-1-hydroxy-5-tert-butyldimethylsilyloxy-1,4-epoxyheptadecane
  参考文献：
  名称：

  Study of the structure-activity relationships of the acetogenin of annonaceae, muricatacin and analogues

  摘要：

  A study of the structure-cytotoxic activity of the acetogenin of Annonaceae, muricatacin 1, is reported. Indeed, muricatacin 1 has shown promising antitumoral activity. Therefore several 5-hydroxy-4-alkanolides were prepared and then tested against KB and VERO cell lines. A few other analogues were synthesized and tested against both cell lines. Thus this work allowed us to better determine the pharmacophore of the molecule and to propose muricatacin 1 instead of a more complicated acetogenin of Annonaceae as a lead compound in the search for new antineoplastic agents.

  DOI：

  10.1016/s0223-5234(97)83287-4
• 作为产物：
  描述：

  (S)-(+)-5-氧代-2-四氢呋喃羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 muricatacinone ou (4S)-5-oxo-heptadecan-4-olide
  参考文献：
  名称：

  Stereospecific synthesis of (+)-muricatacin: a biologically active acetogenin derivative

  摘要：

  (+)-muricatacin及其类似物已成功合成，关于C-4和C-5中心的绝对构型没有歧义。文中报告了所测得的比旋光度[α]D值，以及使用KB和VERO细胞系进行的细胞毒性测定结果。

  DOI：

  10.1016/0040-4039(91)80528-e

文献信息

• A chiron approach to the total synthesis of cytotoxic (+)-muricatacin and (+)-5-epi-muricatacin from d-ribose
  作者：Partha Ghosal、Vikas Kumar、Arun K. Shaw

  DOI：10.1016/j.carres.2009.09.021

  日期：2010.1

  A chiron approach strategy toward the total synthesis of (+)-muricatacin and (+)-5-epi-muricatacin starting from commercially available and inexpensive d-ribose through the key intermediate (S)-5-((R)-1-hydroxyallyl)furan-2(5H)-one has been disclosed.

  从商业上便宜的d-核糖开始，通过关键中间体（S）-5-（（R）-1-）合成（+）-muricatacin和（+）-5-epi-muricatacin的卡隆方法已经公开了羟基烯丙基）呋喃-2（5H）-1。
• First synthesis of a new acetogenin of annonaceae, reticulatamol : Activated tin hydride with enhanced reducing ability
  作者：Vu Thi Tam、Christophe Chaboche、Bruno Figadère、Bertrand Chappe、Bui Chi Hieu、André Cavé

  DOI：10.1016/s0040-4039(00)75989-2

  日期：1994.1

  A new annonaceous acetogenin, reticulatamol 1, is described. In order to confirm its structure, its total synthesis has been performed, using as a key step a radical coupling reaction between an alkyl iodide and an enone, followed by an original reduction of the so obtained ketone to yield the desired natural product.

  描述了一种新的非丙酮生黄素，网状维他命1。为了确认其结构，已进行了全部合成，其中关键的步骤是使用烷基碘与烯酮之间的自由基偶联反应，然后将得到的酮还原，得到所需的天然产物。
• Carbonyl Reduction of Functionalized Aldehydes and Ketones by Tri-n-Butyltin Hydride and SiO2
  作者：Bruno Figadere、Christophe Chaboche、Xavier Franck、Jean-Francois Peyrat、Andre Cave

  DOI：10.1021/jo00102a048

  日期：1994.11
• Enantioselective synthesis of δ-ketobutanolides from (l)-glutamic acid via organomanganese reagents
  作者：Gérard Cahiez、Eric Métais

  DOI：10.1016/s0957-4166(97)00099-2

  日期：1997.5

  Various optically active delta-ketobutanolides were easily prepared in good yields, with an excellent enantiomeric purity, by acylation of organomanganese reagents with the butyrolactone acid chloride 3 prepared from natural (L)-glutamic acid. The reaction takes place in THF under mild conditions (-10 degrees C, 3h or 3% CuCl, -30 degrees C, 20 min.). (C) 1997 Elsevier Science Ltd.