(S)-5-methyl-3-(non-8-enyl)furan-2(5H)-one | 220408-13-9

• 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: (S)-5-methyl-3-(non-8-enyl)furan-2(5H)-one
• 英文别名: (2S)-2-methyl-4-non-8-enyl-2H-furan-5-one
• CAS: 220408-13-9
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: UHOFTAOVWHQYER-LBPRGKRZSA-N

物化性质

• 沸点：
  353.9±21.0 °C(Predicted)
• 密度：
  0.943±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-5-methyl-3-(non-8-enyl)furan-2(5H)-one 在 间氯过氧苯甲酸 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 生成 (5S,5'S)-3,3'-(9,9'-(ethane-1,2-diylbis(azanediyl))bis(8-hydroxynonane-9,1-diyl))bis(5-methylfuran-2(5H)-one)
  参考文献：
  名称：

  Design, synthesis of symmetrical bivalent mimetics of annonaceous acetogenins and their cytotoxicities

  摘要：

  A new series of linear dimeric compounds mimicking naturally occurring annonaceous acetogenins have been synthesized by bivalent analogue design, and their cytotoxicities have been evaluated against the growth of cancer cells by MTT method. Most of these compounds show selective action favored to human cancer cell lines over normal cell lines, and compound 9 with bis-terminal benzoquinone functionality exhibits an IC(50) = 0.40 mu M against MCF7 cell lines. This work mentions that appropriate conformational constraints might be a useful optimizing tool for this unique class of anticancer compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.095
• 作为产物：
  描述：

  10-烯酸甲酯 在 硫酸 、 三乙胺 、 三氟乙酸酐 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 生成 (S)-5-methyl-3-(non-8-enyl)furan-2(5H)-one
  参考文献：
  名称：

  并行片段组装策略，可用于抗癌的无核产乙酸原素的多醚模拟。

  摘要：

  DOI：

  10.1002/anie.200352681

文献信息

• Potent Antitumor Mimetics of Annonaceous Acetogenins Embedded with an Aromatic Moiety in the Left Hydrocarbon Chain Part
  作者：Qicai Xiao、Yongqiang Liu、Yatao Qiu、Guangbiao Zhou、Chan Mao、Zheng Li、Zhu-Jun Yao、Sheng Jiang

  DOI：10.1021/jm101053k

  日期：2011.1.27

  Annonaceous acetogenins are a large family of naturally occurring polyketides exhibiting remarkable anticancer activities. The first generation of annonaceous acetogenin mimetic (1, AA005) exhibits comparable activity as that of natural products and presents much higher selectivity between cancer and normal cells. In this work, we report the design, synthesis, and evaluation of a new series of compound

  丙酮酸非生成素是一大类天然聚酮化合物，表现出显着的抗癌活性。第一代非丙酮产乙酸原素模拟物（1，AA005）具有与天然产物相当的活性，并且在癌症细胞与正常细胞之间具有更高的选择性。在这项工作中，我们报告了一系列新的化合物1类似物的设计，合成和评估，在这些化合物中，各种构象受限的片段嵌入了左侧的烃链部分。已鉴定出具有联苯部分的化合物7具有更强的抗增殖活性，并且比正常细胞优先靶向癌细胞，因此代表了进一步优化的新线索。
• Total Synthesis of the Cytotoxic <i>Threo</i>, <i>Trans</i>, <i>Erythro</i>, <i>Cis</i>, <i>Threo</i> Annonaceous Acetogenin Trilobin
  作者：James A. Marshall、Hongjian Jiang

  DOI：10.1021/jo982057y

  日期：1999.2.1

  A synthesis of trilobin, a new stereochemical varient of the adjacent bis-tetrahydrofuran subgroup of the Annonaceous acetogenins, is described. The synthesis involves three stereochemically defining carbon-carbon bond-forming steps. The first of these introduces the C23-C24 stereocenters and the left side chain by means of an S(E)2' addition of the nonracemic 11-carbon gamma-oxygenated allylic indium

  描述了三叶草蛋白的合成，三叶草蛋白是Annanoaceous acetogenins的相邻双-四氢呋喃亚基的新立体化学变体。该合成涉及三个立体化学定义的碳-碳键形成步骤。这些中的第一个通过S（E）2'的方式将C23-C24立体中心和左侧链引入，该S（E）2'将衍生自α-氧化的烯丙基锡烷4的非外消旋的11-碳γ-氧化的烯丙基铟试剂引入C24 -C16核心醛3.第二个通过BF（3）促进的S（E）2'向C16添加非外消旋的6碳γ-氧化烯丙基锡11形成C15-C16立体中心和右链的一部分。 -C34醛10。第三种方法是在手性双磺酰胺催化剂存在下，向C10-C34醛15中添加二烷基锌试剂17，以建立C10立体中心，同时添加右链的C1-C9残基。通过C1-C34酯与受保护的（S）-丙醛23的缩合来附加C36立体中心和丁烯内酯。
• A TBAF-mediated Chemoselective Method for Synthesis of 4-Methylbutenolides and 4-Hydroxy-4-methylbutenolides from 3-Hydroxy-4-(<i>tert</i>-butyldimethylsilyloxy)pentanoates
  作者：Chunhong Li、Jijun Xue、Baiyan Xu、Zhixiang Xie、Ying Li

  DOI：10.1246/cl.2007.1058

  日期：2007.8.5

  A chemoselective synthesis of butenolides was found based on TBAF-mediated deprotection, cyclization, dehydration, and oxidation of 3-hydroxy-4-(tert-butyldimethylsilyloxy)pentanoates, which yielded either 4-methylbutenolides or 4-hydroxy-4-methylbutenolides in moderate to good yields. The selectivity depends on the quantity of TBAF. This method was applied to the synthesis of several 4-butenolide compounds.

  基于 TBAF 介导的 3-羟基-4-(叔丁基二甲基甲硅烷氧基)戊酸酯的脱保护、环化、脱水和氧化，发现了丁烯酸内酯的化学选择性合成，其以中等速率生成 4-甲基丁烯酸内酯或 4-羟基-4-甲基丁烯酸内酯。以获得良好的产量。选择性取决于 TBAF 的数量。该方法应用于多种4-丁烯内酯化合物的合成。
• Synthesis of a tetra-deuterium-labeled derivative of potent and selective anticancer agent AA005
  作者：Hai-Xia Liu、Zhu-Jun Yao

  DOI：10.1016/j.tetlet.2005.03.123

  日期：2005.5

  Annonaceous acetogenins are a series of potent naturally occurring anticancer agents, which act as inhibitors of complex I in mitochondria. AA005, a mimicry of acetogenins, has been found as active as those natural products and to present high selectivities between cancer and normal cells. In order to investigate the further cell-based mechanism induced by AA005, a d(4)-labeled derivative of AA005 (AA005-d(4)) was designed to detect the drug permeation ability into the membranes. In this letter, the synthesis is reported of this deuterium-labeled compound, wherein a ethylene-d(4) glycol unit is incorporated efficiently into the molecule skeleton by simple etherifications. (c) 2005 Elsevier Ltd. All rights reserved.
• Parallel Fragment Assembly Strategy Towards Multiple-Ether Mimicry of Anticancer Annonaceous Acetogenins
  作者：Sheng Jiang、Yan Li、Xiao-Guang Chen、Tai-Shan Hu、Yu-Lin Wu、Zhu-Jun Yao

  DOI：10.1002/anie.200352681

  日期：2004.1.5