(5Z)-5-[(2E,4E,6E)-十四碳-2,4,6-三烯-8,10-二炔亚基]呋喃-2-酮 | 132971-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: (5Z)-5-[(2E,4E,6E)-十四碳-2,4,6-三烯-8,10-二炔亚基]呋喃-2-酮
• 英文名称: (5Z)-5-[(2E,4E,6E)-tetradeca-2,4,6-triene-8,10-diynylidene]furan-2(5H)-one
• 英文别名: dihydroxerulin；(5Z)-5-[(2E,4E,6E)-tetradeca-2,4,6-trien-8,10-diynylidene]furan-2-one
• CAS: 132971-60-9
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: JHEBXSRENKVLHY-WUHVYRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-2-penten-4-yn-1-ol 在 正丁基锂 、 三氟化硼乙醚 、 sodium bromide 作用下， 以 乙腈 为溶剂， 反应 26.05h， 生成 (5Z)-5-[(2E,4E,6E)-十四碳-2,4,6-三烯-8,10-二炔亚基]呋喃-2-酮
  参考文献：
  名称：

  First Total Synthesis of Dihydroxerulin, a Potent Inhibitor of the Biosynthesis of Cholesterol

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19980615)4:6<1116::aid-chem1116>3.0.co;2-5

文献信息

• Total Synthesis of Polyene Natural Product Dihydroxerulin by Mild Organocatalyzed Dehydrogenation of Alcohols
  作者：Hexin Xie、Shilei Zhang、Hao Li、Xinshuai Zhang、Sihan Zhao、Zian Xu、Xixi Song、Xinhong Yu、Wei Wang

  DOI：10.1002/chem.201103325

  日期：2012.2.20

  Polyene synthesis: An efficient approach to the total synthesis of polyene natural product dihydroxrulin (1) is described. A novel, mild, direct organocatalytic IBX‐mediated dehydrogenation process of simple alcohols to enals has been developed, which serves as a key step in the synthesis (see scheme).

  多烯合成：描述了一种多烯天然产物二氢木鲁林（1）的全合成的有效方法。已经开发了一种新颖的，温和的，直接的由有机醇IBX介导的简单醇脱氢制氢成烯醛的方法，这是合成中的关键步骤（参见方案）。
• Stereoselective Syntheses of Dihydroxerulin and Xerulinic Acid, Anti-Hypocholesterolemic Dyes from the Fungus<i>Xerula melanotricha</i>
  作者：Achim Sorg、Konrad Siegel、Reinhard Brückner

  DOI：10.1002/chem.200400913

  日期：2005.2.18

  inhibitors of the biosynthesis of cholesterol, were synthesized in a convergent and perfectly stereoselective manner. In the key step, bromobutenolide 6 (obtained from levulinic acid in two steps) was coupled with either of the novel bis(stannanes) trans,cis,trans-35 or trans,trans,trans-35 [each accessible from 3-(tributylstannyl)allyl alcohol (17) in four steps], giving gamma-alkylidenebutenolide trans

  以会聚且完全立体选择性的方式合成了作为胆固醇生物合成抑制剂的标题化合物2和3。在关键步骤中，将溴丁烯内酯6（分两步从乙酰丙酸中获得）与新型双（stannanes）反式，顺式，反式-35或反式，反式，反式-反式35偶联[每个都可从3-（三丁基锡烷基）获得醇）（17个步骤，共分四个步骤），得到γ-亚烷基亚丁烯内酯trans，trans，trans-32。该化合物与碘二炔42或溴代二炔酸酯44偶合，分别产生二氢干蛋白（2）和干蛋白酸的（三甲基甲硅烷基乙基）酯45。后者的脱保护首次提供了完全合成的木藻酸（3）。
• METHYLENE FURANONE DERIVATIVES AND USE OF SAID DERIVATIVES AS A PHOTOPROTECTING OR ANTIOXIDANT OR DEPIGMENTATION AGENT IN COSMETIC OR DERMATOLOGICAL COMPOSITIONS
  申请人：Marchal Estelle

  公开号：US20110184059A1

  公开（公告）日：2011-07-28

  The present invention relates to novel methylene furanone derivatives as well as the use thereof as a protective, antioxidant, or depigmentation agent in cosmetic or dermatological compositions. The invention also relates to a method for preparing said derivatives involving a Suzuki-Miyaura coupling reaction from corresponding dibromofuranone derivatives. The invention also relates to a method of preparation involving a coupling reaction of 2-methoxy-furan derivatives with a ketone followed by dehydration.

  本发明涉及新型亚甲基呋喃酮衍生物，以及其作为化妆品或皮肤科组合物中的保护剂、抗氧化剂或脱色剂的用途。该发明还涉及一种制备所述衍生物的方法，涉及从相应的二溴呋喃酮衍生物中进行Suzuki-Miyaura偶联反应的方法。该发明还涉及一种涉及2-甲氧基呋喃衍生物与酮进行偶联反应，然后脱水的制备方法。
• A New Stereocontrolled Synthesis of Dihydroxerulin, a Potent Noncytotoxic Inhibitor of the Biosynthesis of Cholesterol
  作者：Renzo Rossi、Fabio Bellina、Antonella Catanese、Luisa Mannina、Daniela Valensin

  DOI：10.1016/s0040-4020(99)01030-3

  日期：2000.1

  Dihydroxerulin, 1, has been stereoselectively synthesized by a convergent approach in which a key step was the Wittig reaction between (Z)-5-[(E)-3-formyl-2-propenylidene]-5H-furan-2-one, 15, and the phosphonium ylid which derived from [(E)-2-decen-4,6-diyn-1-yl]triphenylphosphonium bromide, 19. Compound 19 was conveniently prepared by a short reaction sequence involving a Stille reaction between 1-trimethylstannyl-1

  Dihydroxerulin，1，已被立体选择性地由一个会聚的方法，其中一个关键步骤是（之间的Wittig反应ž [（ - ）-5 Ë）-3-甲酰基-2-亚丙烯基] -5- ħ -呋喃-2-酮，15，和衍生自[（E）-2-decen-4,6-diyn-1-yl]三苯基溴化phosph的磷鎓基吡啶，19。化合物19可通过短反应序列方便地制备，该短反应序列涉及1-三甲基锡烷基-1,3-庚二炔17和18（E）-3-碘-2-丙烯1-ol 18之间的Stille反应。另一方面，化合物15通过八步反应顺序制备丁烯内酯的直接前体，即（Z）-5-[（2 E）-4-羟基-2-丁烯叉] -5 H-呋喃-2-酮，34通过Ag（I）催化的相应的（Z）-2-en-4-炔酸的内酯化在区域和立体上选择性地合成。的结构和立体化学的1被它的基础上建立的1 H和13 C NMR光谱在600和150 MHz的，分别与通过2D NMR技术的组合。
• An Efficient Method for the Production of Terminal Alkynes from 1,1-Dibromo-1-alkenes and its Application in the Total Synthesis of Natural Product Dihydroxerulin
  作者：Shihui Liu、Xiaobei Chen、Yanwei Hu、Laiqi Yuan、Shaohua Chen、Ping Wu、Wei Wang、Shilei Zhang、Wei Zhang

  DOI：10.1002/adsc.201400782

  日期：2015.2.9

  AbstractAn efficient method of preparing various terminal alkynes from 1,1‐dibromo‐1‐alkenes by using TBAF (tetra‐n‐butylammonium fluoride) as a base and triphenylphosphane as a reductant was developed. This method is strong base and low/high temperatures free, and can tolerate a broad range of substrates. These advantages were well demonstrated by the application of this method to the total synthesis of polyene natural product dihydroxerulin.magnified image