((3S,4R,5S,6S,E)-3,5-Dimethoxy-4,6-dimethyloct-1-en-7-yn-1-yl)benzene | 890409-88-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((3S,4R,5S,6S,E)-3,5-Dimethoxy-4,6-dimethyloct-1-en-7-yn-1-yl)benzene
• 英文别名: ((3S,4R,5S,6S,7E)-3,5-dimethoxy-4,6-dimethyloct-1-en-7-ynyl)benzene；((3S,4R,5S,6S,E)-3,5-dimethoxy-4,6-dimethyloct-1-ene-7-ynyl)benzene；(3S,4R,5S,6S,7E)-4,6-dimethoxy-3,5-dimethyl-8-phenyloct-7-en-1-yne；[(E,3S,4R,5S,6S)-3,5-dimethoxy-4,6-dimethyloct-1-en-7-ynyl]benzene
• CAS: 890409-88-8
• 化学式: C₁₈H₂₄O₂
• 分子量: 272.387
• InChiKey: AXOJNQPVRUDDJH-HSNQEXALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((3S,4R,5S,6S,E)-3,5-Dimethoxy-4,6-dimethyloct-1-en-7-yn-1-yl)benzene 在 bis-triphenylphosphine-palladium(II) chloride 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 反应 60.25h， 生成 (2E,4E,6S,7S,8R,9S,10E)-7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienoic acid
  参考文献：
  名称：

  Formal Total Syntheses of Crocacin A-D

  摘要：

  本文介绍了一种简明的方法，用于合成蝎子碱A-D（1-4）中的常见多酮片段5，该方法之前已被多种方式转化为这种真菌杀菌和细胞毒素家族的所有成员。我们的合成特点是使用了一种由缬氨醇衍生的辅助剂控制的钛醛反应，并且采用了锌介导的、钯催化的反式选择性丙炔基甲烷磺酸酯10加到手性醛9上的方法，同时比较了钯催化的Stille和Suzuki交叉偶联反应来形成目标化合物的二烯基基团。

  DOI：

  10.1135/cccc20051696
• 作为产物：
  描述：

  (2R,3R,4E)-3-Methoxy-2-methyl-5-phenyl-4-pentenal 在 diethylzinc 、 palladium diacetate 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.25h， 生成 ((3S,4R,5S,6S,E)-3,5-Dimethoxy-4,6-dimethyloct-1-en-7-yn-1-yl)benzene
  参考文献：
  名称：

  Diastereoselective synthesis of an advanced intermediate of the crocacin family using asymmetric transfer hydrogenation-DKR and Marshall allenylation as key reactions

  摘要：

  The natural product of a crocacin-family structural scaffold bearing consecutive anti-anti-syn stereogenic centers was accomplished by means of ATH-DKR and Marshall allenylation reactions with high stereo-control levels. The salient feature of this process is that a single catalytic asymmetric Ru-complex was used for the chirality genesis of pivotal reactions with a high substrate-to-catalyst ratio. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.057

文献信息

• Total Synthesis of (+)-Crocacin C Using Hidden Symmetry
  作者：Mathieu Candy、Gérard Audran、Hugues Bienaymé、Cyril Bressy、Jean-Marc Pons

  DOI：10.1021/jo902582w

  日期：2010.3.5

  A highly convergent and protecting-group-free synthesis of (+)-crocacin C, featuring an enzymatic enantioselective desymmetrization of a meso-diol, a base-induced ring opening of a THP ring, and a one-pot hydrostannylation/Stille coupling as the key steps, is reported. The natural product was obtained in 11 steps and 22.3% overall yield starting from readily available oxabicycle 1. Finally, a unique enantioselective step, an enzymatic desymmetrization, revealed four stereogenic centers and created one in C4 of the THP furnishing the dense building block 4 with high enantioselectivity (ce >98%).
• Step-Economic Synthesis of (+)-Crocacin C: A Concise Crotylboronation/[3,3]-Sigmatropic Rearrangement Approach
  作者：Adele E. Pasqua、Frank D. Ferrari、Chris Hamman、Yanzhou Liu、James J. Crawford、Rodolfo Marquez

  DOI：10.1021/jo301210f

  日期：2012.8.17

  The step-economic total synthesis of (+)-crocacin C has been achieved in 20% yield from commercially available starting materials. This approach requires the isolation of only 8 intermediates and can provide a reliable supply of (+)-crocacin C for the development of new antifungal and crop protection agents.