(3R,4S,6R)-9-(benzyloxy)-6-(4-(methoxybenzyl)oxy)-3-methylnon-1-en-4-ol | 1309595-74-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R,4S,6R)-9-(benzyloxy)-6-(4-(methoxybenzyl)oxy)-3-methylnon-1-en-4-ol
• 英文别名: (3R,4S,6R)-6-[(4-methoxyphenyl)methoxy]-3-methyl-9-phenylmethoxynon-1-en-4-ol
• CAS: 1309595-74-1
• 化学式: C₂₅H₃₄O₄
• 分子量: 398.543
• InChiKey: ULPZRKMPHOSCGK-ZPZUNKDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,6R)-9-(benzyloxy)-6-(4-(methoxybenzyl)oxy)-3-methylnon-1-en-4-ol 在 吡啶 、 camphor-10-sulfonic acid 、 臭氧 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.75h， 生成 (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：

  1-(benzyloxy)-4,5-epoxypentane 在 吡啶 、 copper(l) iodide 、 (4S,5S)-chloro(cyclopentadienyl)(2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato-O,O^α)titanium 、 C₃₈H₅₅CoN₂O₄ 、 水 、 四丁基碘化铵 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 mineral oil 为溶剂， 反应 19.83h， 生成 (6R)-9-(benzyloxy)-6-(4-(methoxybenzyl)oxy)-3-methylnon-1-en-4-ol 、 (3R,4S,6R)-9-(benzyloxy)-6-(4-(methoxybenzyl)oxy)-3-methylnon-1-en-4-ol
  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

• 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.