(5Z)-5-[(2E,4E,6E,12E)-十四碳-2,4,6,12-四烯-8,10-二炔亚基]呋喃-2-酮 | 132971-61-0

• 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,12E)-十四碳-2,4,6,12-四烯-8,10-二炔亚基]呋喃-2-酮
• 英文名称: xerulin
• 英文别名: (5Z)-5-[(2E,4E,6E,12E)-tetradeca-2,4,6,12-tetraen-8,10-diynylidene]furan-2-one
• CAS: 132971-61-0
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: NVTZKVXKAGVWNW-KKNDAJMBSA-N

物化性质

• 熔点：
  166-168 °C
• 沸点：
  476.5±37.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  反式,反式-5-溴-2,4-戊二醛 在 bis-triphenylphosphine-palladium(II) chloride 、 tetrakis(triphenylphosphine)palladium dichloride copper(l) iodide 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 12.0h， 生成 (5Z)-5-[(2E,4E,6E,12E)-十四碳-2,4,6,12-四烯-8,10-二炔亚基]呋喃-2-酮
  参考文献：
  名称：

  New stereoselective methodology for the synthesis of dihydroxerulin and xerulin, potent inhibitors of the biosynthesis of cholesterol

  摘要：

  A new stereoselective methodology for the synthesis of both dihydroxerulin and xerulin has been devised. The key step required cross-coupling reactions between the bromo trienyne, (1E,3E,5E)-l-bromo-8-trimethylsilyl-1,3,5-octatrien-7-yne and the appropriate conjugated diynes. The palladium-catalyzed tandem cross-coupling/cyclization reaction of the resulting polyenynes with (Z)-3-iodo-2-propenoic acid led directly to dihydroxerulin or xerulin with a high degree of stereoselectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.085

文献信息

• An Efficient and Stereoselective Synthesis of Xerulin <i>via</i> Pd-Catalyzed Cross Coupling and Lactonization Featuring (<i>E</i>)-Iodobromoethylene as a Novel Two-Carbon Synthon
  作者：Ei-ichi Negishi、Asaf Alimardanov、Caiding Xu

  DOI：10.1021/ol990336h

  日期：2000.1.1

  [structure: see text] Xerulin, an inhibitor of cholesterol biosynthesis, has been synthesized from commercially available (E)-1-bromopropene, acetylene, and propynoic acid in five steps (longest linear sequence) in 30% overall yield and >96% stereoselectivity. The preparation of (E)-iodobromoethylene and its use in the Pd-catalyzed cross coupling are two of the novel aspects of the synthesis reported

  [结构：参见文本]胆固醇生物合成抑制剂Xerulin由市售（E）-1-溴丙烯，乙炔和丙酸经五个步骤（最长的线性序列）合成，总收率30％，> 96％立体选择性。（E）-碘溴乙烯的制备及其在Pd催化的交叉偶联中的用途是本文报道的合成的两个新颖方面。
• First Synthesis of Xerulin, an Inhibitor of the Biosynthesis of Cholesterol
  作者：Konrad Siegel、Reinhard Brückner

  DOI：10.1055/s-1999-3162

  日期：1999.8
• New stereoselective methodology for the synthesis of dihydroxerulin and xerulin, potent inhibitors of the biosynthesis of cholesterol
  作者：Vito Fiandanese、Daniela Bottalico、Giuseppe Marchese、Angela Punzi

  DOI：10.1016/j.tet.2004.09.085

  日期：2004.12

  A new stereoselective methodology for the synthesis of both dihydroxerulin and xerulin has been devised. The key step required cross-coupling reactions between the bromo trienyne, (1E,3E,5E)-l-bromo-8-trimethylsilyl-1,3,5-octatrien-7-yne and the appropriate conjugated diynes. The palladium-catalyzed tandem cross-coupling/cyclization reaction of the resulting polyenynes with (Z)-3-iodo-2-propenoic acid led directly to dihydroxerulin or xerulin with a high degree of stereoselectivity. (C) 2004 Elsevier Ltd. All rights reserved.