(2Z,4E)(R)-(+)-caparratriene

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2Z,4E)(R)-(+)-caparratriene
• 英文别名: (2Z,4E,7R)-3,7,11-trimethyldodeca-2,4,10-triene
• 化学式: C₁₅H₂₆
• 分子量: 206.371
• InChiKey: GIBJEWOSWWYJSK-VPHKHRPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (+)-香茅醛 、 1-(2E,2-methylbutenyl)triethylphosphonium bromide 在 lithium chloride 、 lithium hydroxide 作用下， 以 水 为溶剂， 反应 3.03h， 生成 (2Z,4E)(R)-(+)-caparratriene 、 (2E,4E)(R)-(+)-caparratriene
  参考文献：
  名称：

  A short synthesis of the anti-leukemic sesquiterpene (+)-caparratriene employing aqueous Wittig chemistry

  摘要：

  An efficient, stereoselective method for the synthesis of (+)-caparratriene based on an aqueous Wittig reaction has been developed. A functionalized triethylallyl ylide reacted under various conditions with (+)-citronellal to deliver (+)-caparratriene in only three steps with excellent overall yield. The Wittig reaction proceeded with exclusive (4E)-selectivity and an interesting cationic effect was uncovered with good stereoselectivity at the isomerizable allylic position being observed in the presence of lithium salts. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.035

文献信息

• Wittig Reactions of Trialkylphosphine-derived Ylides: New Directions and Applications in Organic Synthesis
  作者：James McNulty、David McLeod、Priyabrata Das、Carlos Zepeda-Velázquez

  DOI：10.1080/10426507.2014.980907

  日期：2015.6.3

  ylides derived from short-chain trialkylphosphines in the Wittig-type olefination reactions toward the synthesis of alkenes, including stilbenes, styrenes, and 1,3-dienes, as well as reagents for homologation reactions, are described. The methods allow easy access to alkenes with high (E)-stereoselectivity in good yield. These reactions are conducted with weak bases in aqueous media, which allows easy

  图形摘要 摘要 在 Wittig 型烯化反应中，从短链三烷基膦衍生的半稳定、稳定和功能化叶立德的发展，以合成烯烃，包括二苯乙烯、苯乙烯和 1,3-二烯，以及试剂对于同系化反应，进行了描述。该方法允许以良好的收率轻松获得具有高 (E) 立体选择性的烯烃。这些反应是在水性介质中用弱碱进行的，这使得水溶性氧化膦很容易分离。还描述了用于 Wittig 反应的温和有机催化过程的发展以及在生物条件下制备报道二苯乙烯的延伸。讨论了在制备生物活性天然产物和衍生物方面的应用。
• A short synthesis of the anti-leukemic sesquiterpene (+)-caparratriene employing aqueous Wittig chemistry
  作者：Priyabrata Das、James McNulty

  DOI：10.1016/j.tetlet.2010.04.035

  日期：2010.6

  An efficient, stereoselective method for the synthesis of (+)-caparratriene based on an aqueous Wittig reaction has been developed. A functionalized triethylallyl ylide reacted under various conditions with (+)-citronellal to deliver (+)-caparratriene in only three steps with excellent overall yield. The Wittig reaction proceeded with exclusive (4E)-selectivity and an interesting cationic effect was uncovered with good stereoselectivity at the isomerizable allylic position being observed in the presence of lithium salts. (C) 2010 Elsevier Ltd. All rights reserved.