1-((1E,3S,4R,5S,6S,7E)-8-iodo-3,5-dimethoxy-4,6-dimethylocta-1,7-dienyl)benzene | 387821-97-8

• 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: 1-((1E,3S,4R,5S,6S,7E)-8-iodo-3,5-dimethoxy-4,6-dimethylocta-1,7-dienyl)benzene
• 英文别名: ((1E,3S,4R,5S,6S,7E)-8-Iodo-3,5-dimethoxy-4,6-dimethylocta-1,7-dienyl)benzene；[(1E,3S,4R,5S,6S,7E)-8-iodo-3,5-dimethoxy-4,6-dimethylocta-1,7-dienyl]benzene
• CAS: 387821-97-8
• 化学式: C₁₈H₂₅IO₂
• 分子量: 400.3
• InChiKey: YUMNINJGKQFEJW-FXKZPPSLSA-N

物化性质

• 沸点：
  429.6±45.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  8
• 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：

  1-((1E,3S,4R,5S,6S,7E)-8-iodo-3,5-dimethoxy-4,6-dimethylocta-1,7-dienyl)benzene 在 tris(dibenzylideneacetone)dipalladium (0) copper(l) iodide 、 三苯胂 、 caesium carbonate 、 copper(l) chloride 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 31.0h， 生成 methyl 2-((Z)-6-((2E,4E,6S,7S,8R,9S,10E)-7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienamido)hex-5-enamido)acetate
  参考文献：
  名称：

  Total Synthesis of (+)-Crocacin D

  摘要：

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.

  DOI：

  10.1021/jo047732k
• 作为产物：
  描述：

  tert-butyl((2S,3S,4R,5S,E)-3,5-dimethoxy-2,4-dimethyl-7-phenylhept-6-enyloxy)diphenylsilane 在 chromium dichloride 、 四丁基氟化铵 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.17h， 生成 1-((1E,3S,4R,5S,6S,7E)-8-iodo-3,5-dimethoxy-4,6-dimethylocta-1,7-dienyl)benzene
  参考文献：
  名称：

  Step-Economic Synthesis of (+)-Crocacin C: A Concise Crotylboronation/[3,3]-Sigmatropic Rearrangement Approach

  摘要：

  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.

  DOI：

  10.1021/jo301210f

文献信息

• Total Synthesis of (+)-Crocacin C
  作者：Luiz C. Dias、Luciana G. de Oliveira

  DOI：10.1021/ol016845c

  日期：2001.11.1

  [GRAPHICS]The total synthesis of (+)-crocacin C is described. The convergent asymmetric synthesis relies on the use of a regio- and diastereoselective epoxidation of an allylic alcohol with m-CPBA followed by epoxide opening with Me2CuCNLi2 and a Stille cross-coupling between E-vinyl stannane 5 and E-vinyl iodide 6 to establish the (E,E)-dienamide moiety.
• Total Synthesis of (+)-Crocacin D
  作者：Luiz C. Dias、Luciana G. de Oliveira、Janaína D. Vilcachagua、Florian Nigsch

  DOI：10.1021/jo047732k

  日期：2005.3.1

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.
• 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.