1-methoxy-4-[[(3R,4S,6R)-6-[(4-methoxyphenyl)methoxy]-3-methyl-9-phenylmethoxynon-1-en-4-yl]oxymethyl]benzene | 1309595-75-2

• 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-methoxy-4-[[(3R,4S,6R)-6-[(4-methoxyphenyl)methoxy]-3-methyl-9-phenylmethoxynon-1-en-4-yl]oxymethyl]benzene
• CAS: 1309595-75-2
• 化学式: C₃₃H₄₂O₅
• 分子量: 518.693
• InChiKey: JFFABMDMRFBBFD-DJBQJLJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  38
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methoxy-4-[[(3R,4S,6R)-6-[(4-methoxyphenyl)methoxy]-3-methyl-9-phenylmethoxynon-1-en-4-yl]oxymethyl]benzene 在 吡啶 、 臭氧 、 二甲基硫 、 氧气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.75h， 以75%的产率得到(2R,3S,5R)-8-(benzyloxy)-3,5-bis((4-methoxybenzyl)oxy)-2-methyloctanal
  参考文献：
  名称：

  Highly Demanding Cross-Metathesis in the Synthesis of the C16–C30 Fragment of Dolabelide C

  摘要：

  A highly demanding cross-metathesis (CM) reaction for the formation of the C24-C25 trisubstituted olefin of dolabelide C has been optimized. A difference in reactivity between the E and Z enone isomers in this reaction was uncovered, and the selection of the Z isomer of the starting enone was critical for the success of the cross-metathesis. Application to the synthesis of the C16-C30 fragment of dolabelide C is reported.

  DOI：

  10.1021/jo200466t
• 作为产物：
  描述：

  (R)-7-(benzyloxy)-4-((4-methoxybenzyl)oxy)hept-1-ene 在 吡啶 、 (4S,5S)-chloro(cyclopentadienyl)(2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato-O,O^α)titanium 、 camphor-10-sulfonic acid 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 17.83h， 生成 1-methoxy-4-[[(3R,4S,6R)-6-[(4-methoxyphenyl)methoxy]-3-methyl-9-phenylmethoxynon-1-en-4-yl]oxymethyl]benzene
  参考文献：
  名称：

  Highly Demanding Cross-Metathesis in the Synthesis of the C16–C30 Fragment of Dolabelide C

  摘要：

  A highly demanding cross-metathesis (CM) reaction for the formation of the C24-C25 trisubstituted olefin of dolabelide C has been optimized. A difference in reactivity between the E and Z enone isomers in this reaction was uncovered, and the selection of the Z isomer of the starting enone was critical for the success of the cross-metathesis. Application to the synthesis of the C16-C30 fragment of dolabelide C is reported.

  DOI：

  10.1021/jo200466t

文献信息

• Novel Synthesis of Trisubstituted Olefins for the Preparation of the C16–C30 Fragment of Dolabelide C
  作者：Alexander F. Tiniakos、Stéphane Wittmann、Alexandre Audic、Joëlle Prunet

  DOI：10.1021/acs.orglett.8b03552

  日期：2019.2.1

  for the synthesis of trisubstituted olefins flanked by allylic or homoallylic alcohols, which are difficult to obtain by classical ring-closing or cross-metathesis reactions. In addition, a novel Peterson olefination reaction has been developed for the preparation of the allyldimethylsilane precursors, which are versatile synthetic intermediates. This method was then applied to the synthesis of the

  据报道，硅系环闭环易位策略用于合成侧接烯丙基或均烯丙基醇的三取代烯烃，这是传统的闭环或交叉复分解反应难以获得的。另外，已经开发了新颖的彼得森烯化反应用于制备烯丙基二甲基硅烷前体，所述烯丙基二甲基硅烷前体是通用的合成中间体。然后将该方法应用于多标签肽C的C16–C30片段的合成。
• Highly Demanding Cross-Metathesis in the Synthesis of the C16–C30 Fragment of Dolabelide C
  作者：Marie-Gabrielle Braun、Aurélie Vincent、Mehdi Boumediene、Joëlle Prunet

  DOI：10.1021/jo200466t

  日期：2011.6.17

  A highly demanding cross-metathesis (CM) reaction for the formation of the C24-C25 trisubstituted olefin of dolabelide C has been optimized. A difference in reactivity between the E and Z enone isomers in this reaction was uncovered, and the selection of the Z isomer of the starting enone was critical for the success of the cross-metathesis. Application to the synthesis of the C16-C30 fragment of dolabelide C is reported.