(5S)-3-[(R)-2-hydroxynon-8-enyl]-5-methyl-5H-furan-2-one | 915314-45-3

• 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: (5S)-3-[(R)-2-hydroxynon-8-enyl]-5-methyl-5H-furan-2-one
• 英文别名: (2S)-4-[(2R)-2-hydroxynon-8-enyl]-2-methyl-2H-furan-5-one
• CAS: 915314-45-3
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: ZJUWFWDKVRIUNA-WCQYABFASA-N

物化性质

• 沸点：
  408.1±40.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S)-3-[(R)-2-hydroxynon-8-enyl]-5-methyl-5H-furan-2-one 、 [(1S)-1-[(2R,5S)-5-[(1S,4S)-1,4-bis[[tert-butyl(dimethyl)silyl]oxy]-4-[(2S,5R)-5-ethenyloxolan-2-yl]butyl]oxolan-2-yl]undecoxy]-tert-butyl-dimethylsilane 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以79%的产率得到
  参考文献：
  名称：

  Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-cis-Sylvaticin

  摘要：

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.

  DOI：

  10.1021/ja9049959
• 作为产物：
  描述：

  6-溴-1-己烯 在 2,6-二甲基吡啶 、 乙酰氯 、 间氯过氧苯甲酸 、 sodium iodide 、 magnesium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正庚烷 、 二氯甲烷 、 乙基苯 、 丙酮 为溶剂， 反应 78.83h， 生成 (5S)-3-[(R)-2-hydroxynon-8-enyl]-5-methyl-5H-furan-2-one
  参考文献：
  名称：

  Total Synthesis of (+)-cis-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium

  摘要：

  The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.

  DOI：

  10.1021/ja0660148

文献信息

• Asymmetric Total Synthesis of Trilobacin via Organoselenium-Mediated Oxonium Ion Formation/SiO₂-Promoted Fragmentation
  作者：Te-ik Sohn、Mi Jung Kim、Deukjoon Kim

  DOI：10.1021/ja106116v

  日期：2010.9.8

  An asymmetric total synthesis of trilobacin (1), an annonaceous acetogenin with potent anticancer activities, was accomplished wherein the construction of its erythro-bis(2,2')-tetrahydrofuran core 2 featured a novel organoselenium-mediated oxonium ion formation/SiO(2)-promoted fragmentation of alpha,alpha'-cis-oxocene 3.

  完成了三叶菌素 (1) 的不对称全合成，这是一种具有强效抗癌活性的番荔枝素，其中红-双 (2,2')-四氢呋喃核心 2 的构建具有新型有机硒介导的氧鎓离子形成/SiO( 2)-促进 alpha,alpha'-cis-oxocene 3 的片段化。
• Total Synthesis of (+)-<i>cis</i>-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium
  作者：Timothy J. Donohoe、Robert M. Harris、Jeremy Burrows、Jeremy Parker

  DOI：10.1021/ja0660148

  日期：2006.10.1

  The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.
• Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-<i>cis</i>-Sylvaticin
  作者：Timothy J. Donohoe、Robert M. Harris、Oliver Williams、Gráinne C. Hargaden、Jeremy Burrows、Jeremy Parker

  DOI：10.1021/ja9049959

  日期：2009.9.9

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.