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(4S,5S,8S,9S)-9-hydroxy-5,8-epoxyhenicosan-4-olide

中文名称
——
中文别名
——
英文名称
(4S,5S,8S,9S)-9-hydroxy-5,8-epoxyhenicosan-4-olide
英文别名
(5S)-5-[(2S,5S)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]oxolan-2-one
(4S,5S,8S,9S)-9-hydroxy-5,8-epoxyhenicosan-4-olide化学式
CAS
——
化学式
C21H38O4
mdl
——
分子量
354.53
InChiKey
RMIZIDDWTWGDBZ-MUGJNUQGSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    6.2
  • 重原子数:
    25
  • 可旋转键数:
    13
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.95
  • 拓扑面积:
    55.8
  • 氢给体数:
    1
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

点击查看最新优质反应信息

文献信息

  • Stereocontrolled synthesis of key intermediates in the total synthesis of acetogenins of annonaceae
    作者:Bruno Figadère、Christophe Chaboche、Jean-François Peyrat、André Cavé
    DOI:10.1016/s0040-4039(00)61460-0
    日期:1993.12
    (4S, 5S, 8S, 9S)- and (4R, 5S, 8S, 9S)-9-hydroxy-5,8-epoxy-henicosabutanolides 3b and 4b, respectively, have been successfully synthesized from very inexpensive L-glutamic acid. The key step of the synthetic sequence is an alkylation of lactol acetates 5a,b with 2-(trimethylsilyloxy)-furan. Stereochemical relationship assignment of the obtained products were deduced from NMR data, and by chemical correlation
    (4S,5S,8S,9S)-和(4R,5S,8S,9S)-9-羟基-5,8-环氧-丁香醇3b和4b已分别由非常便宜的L-谷氨酸成功合成。合成序列的关键步骤是将乙酸内酯乙酸酯5a,b与2-(三甲基甲硅烷氧基)-呋喃进行烷基化。从NMR数据和通过化学相关推导获得的产物的立体化学关系分配。
  • Acetogenins of annonaceae. Part 86: synthesis of a highly functionalized precursor of (-)-4-deoxygigantecin, an annonaceous acetogenin
    作者:Magali Szlosek、Jean-François Peyrat、Christophe Chaboche、Xavier Franck、Reynald Hocquemiller、Bruno Figadère
    DOI:10.1039/b000236o
    日期:——
    C-glycosylation and (iii) diastereoselective aldolization reactions, all of them using 2-trimethylsilyloxyfuran as nucleophile. This strategy would allow us to prepare squamostatin D as well, another acetogenin of Annonaceae possessing two nonadjacent tetrahydrofuran rings and a closely related tetrahydrofuran pattern.
    从十六烷中经过14步制备了具有六个立体生成中心的(-)-4-deoxygigantecin的高度功能化的前体。关键步骤是(i)对映选择性醛缩反应,(ii)非对映选择性C-糖基化和(iii)非对映选择性醛缩反应,所有这些步骤均使用2-三甲基甲硅烷氧基呋喃作为亲核试剂。这种策略将使我们也可以制备南瓜素D,这是番荔枝科的另一种产黄素, 具有两个不相邻的四氢呋喃环和密切相关的四氢呋喃模式。
  • 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.
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