2(3H)-Furanone, dihydro-5-(1-oxoundecyl)-, (S)- | 54848-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2(3H)-Furanone, dihydro-5-(1-oxoundecyl)-, (S)-
• 英文别名: (5S)-5-undecanoyloxolan-2-one
• CAS: 54848-35-0
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: STIRBIXEVCCOMC-AWEZNQCLSA-N

物化性质

• 沸点：
  395.7±35.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  2(3H)-Furanone, dihydro-5-(1-oxoundecyl)-, (S)- 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 Cl⁽³⁾HO₄ 、 氢气 、 L-Selectride 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 62.75h， 生成 (5S)-5-[(2S,5S)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyundecyl]oxolan-2-yl]oxolan-2-one
  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 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2(3H)-Furanone, dihydro-5-(1-oxoundecyl)-, (S)-
  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

文献信息

• Highly stereoselective preparation of enantiomerically pure 1,2-diols: synthesis of (+)-exobrevicomin
  作者：Marc Larchevêque、Julien Lalande

  DOI：10.1039/c39850000083

  日期：——

  Reduction of optically pure acyl-lactones (2) by L-Selectride affords monoprotected syn diols with high diastereoselectivity; the reaction was applied to the stereo- and enantio-specific synthesis of (+)-exobrevicomin.

  L-Selectride还原光学纯的酰基内酯（2）可以得到具有高非对映选择性的单保护的合成二醇；反应用于（+）-exobrevicomin的立体和对映体特异性合成。
• On the mode of baker's yeast reduction of enantiomeric 4-acyl butanolides
  作者：Giovanni Fronza、Claudio Fuganti、Piero Grasselli、Rosalino Pulido-Fernandez、Stefano Servi、Auro Tagliani、Marco Terreni

  DOI：10.1016/s0040-4020(01)96212-x

  日期：1991.11

  butanolides (R)-(1a) and (R)-(1b), bearing n-alkyl chains, on yeast treatment afford exclusively the syn reduction products (4a) and (4b), whereas the (S) enantiomers yield syn (2a) and (2b) in ca. 6:4 ratio with the anti diastereoisomers (3a) and (3b), respectively. Under the same conditions, (S)-(1c) and (R)-(1c) give rise to syn and anti reduction products in ca. 1:4 and 4:1 ratios, respectively.

  在酵母处理中带有正烷基链的4-酰基丁醇化物（R）-（1a）和（R）-（1b）仅提供合成还原产物（4a）和（4b），而（S）对映异构体syn（2a）和（2b）在ca中。6：4的比例与抗非对映体（3A）和（3B）表示。在相同条件下，（S）-（1c）和（R）-（1c）产生syn和抗还原产物在约 1：4和4：1的比例。
• Larcheveque; Lalande, Bulletin de la Societe Chimique de France, 1987, vol. No. 1, # 1, p. 116 - 122
  作者：Larcheveque、Lalande

  DOI：——

  日期：——
• Study of the structure-activity relationships of the acetogenin of annonaceae, muricatacin and analogues
  作者：A Cavé、C Chaboche、B Figadère、J.C. Harmange、A Laurens、J.F. Peyrat、M Pichon、M Szlosek、J Cotte-Lafitte、A.M. Quéro

  DOI：10.1016/s0223-5234(97)83287-4

  日期：1997.7

  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.