(+)-(5S)-3-(12-dodecen-1-yl)-5-methyl-2(5H)-furanone | 334651-20-6

• 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-(12-dodecen-1-yl)-5-methyl-2(5H)-furanone
• 英文别名: (5S)-3-(11'-dodecenyl)-5-methylfuran-2(5H)-one；(2S)-4-dodec-11-enyl-2-methyl-2H-furan-5-one
• CAS: 334651-20-6
• 化学式: C₁₇H₂₈O₂
• 分子量: 264.408
• InChiKey: BWPRZTNWIXWGLA-HNNXBMFYSA-N

物化性质

• 沸点：
  385.0±11.0 °C(Predicted)
• 密度：
  0.926±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,5R,1'S,1''R)-2-(1'-hydroxy-2'-propenyl)-5-(1''-hydroxytridecyl)tetrahydrofuran 、 (+)-(5S)-3-(12-dodecen-1-yl)-5-methyl-2(5H)-furanone 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到(1'''R,2''S,5S,5''R,13'S)-3-{13'-hydroxy-13'-[5''-(1'''-hydroxytridecyl)tetrahydrofuran-2''-yl]-11'-tridecenyl}-5-methyl-2,5-dihydrofuran-2-one
  参考文献：
  名称：

  Synthesis of solamin type mono-THF acetogenins using cross-metathesis

  摘要：

  The total synthesis of mono-THF acetogenins, cis-solamin A and B, and reticulatacin, was accomplished starting with muricatacin. The backbone of the mono-THF acetogenins was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. Notably, cis-THF compounds were obtained without using protective groups. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.028
• 作为产物：
  描述：

  1,10-癸二醇 在 Lindlar's catalyst 咪唑 、 喹啉 、 六甲基磷酰三胺 、 AD-mix-α 、 正丁基锂 、 甲基磺酰胺 、 四丁基氟化铵 、 氢气 、 碘 、 三乙胺 、 三苯基膦 、 三氟乙酸酐 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 叔丁醇 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 74.75h， 生成 (+)-(5S)-3-(12-dodecen-1-yl)-5-methyl-2(5H)-furanone
  参考文献：
  名称：

  促乙酸素的γ-甲基丁烯内酯单元的Sharpless AD策略：具有蚊幼虫活性的丁烯内酯I和II的对映选择性合成

  摘要：

  基于Sharpless不对称二羟基化技术，以高收率和良好的对映体纯度为基础，建立了一种针对γ-甲基丁烯内酯的新型合成策略。该途径可扩展为合成天然存在的非丙酮产乙酸原素的α，γ-二取代丁烯内酯单元。利用这种策略，对映体选择性合成了三种具有丁烯内酯链段的简单天然产物。

  DOI：

  10.1016/s0040-4020(02)01063-3

文献信息

• Total synthesis of cis-solamin A, a mono-tetrahydrofuran acetogenin isolated from Annona muricata
  作者：Hiroyuki Konno、Yasuhiro Okuno、Hidefumi Makabe、Kazuto Nosaka、Akio Onishi、Yoshinari Abe、Atsuya Sugimoto、Kenichi Akaji

  DOI：10.1016/j.tetlet.2007.11.190

  日期：2008.1

  Total synthesis of cis-solamin A was accomplished without using protecting groups starting from (-)-muricatacin in 11 steps with an overall yield of 4.5%. The backbone of cis-solamin A was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of solamin type mono-THF acetogenins using cross-metathesis
  作者：Hiroyuki Konno、Hidefumi Makabe、Yasunao Hattori、Kazuto Nosaka、Kenichi Akaji

  DOI：10.1016/j.tet.2010.08.028

  日期：2010.10

  The total synthesis of mono-THF acetogenins, cis-solamin A and B, and reticulatacin, was accomplished starting with muricatacin. The backbone of the mono-THF acetogenins was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. Notably, cis-THF compounds were obtained without using protective groups. (C) 2010 Elsevier Ltd. All rights reserved.
• Sharpless AD strategy towards the γ-methyl butenolide unit of acetogenins: enantioselective synthesis of butenolide I and II with mosquito larvicidal activity
  作者：Yan-Tao He、Hui-Na Yang、Zhu-Jun Yao

  DOI：10.1016/s0040-4020(02)01063-3

  日期：2002.10

  butenolides has been established based on Sharpless asymmetric dihydroxylation in high yields and good enantiopurity. The route could be expanded to the synthesis of α,γ-disubstituted butenolide units of naturally occurring annonaceous acetogenins. Utilizing this strategy, three simple natural products with butenolide segments were synthesized enantioselectively.

  基于Sharpless不对称二羟基化技术，以高收率和良好的对映体纯度为基础，建立了一种针对γ-甲基丁烯内酯的新型合成策略。该途径可扩展为合成天然存在的非丙酮产乙酸原素的α，γ-二取代丁烯内酯单元。利用这种策略，对映体选择性合成了三种具有丁烯内酯链段的简单天然产物。