(Z,Z)-heptadeca-7,10-diene | 927670-24-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (Z,Z)-heptadeca-7,10-diene
• 英文别名: (7Z,10Z)-heptadeca-7,10-diene
• CAS: 927670-24-4
• 化学式: C₁₇H₃₂
• 分子量: 236.441
• InChiKey: NCNOGMNPHJHDMX-VMNXYWKNSA-N

物化性质

• 沸点：
  307.5±12.0 °C(Predicted)
• 密度：
  0.797±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (Z,Z)-heptadeca-7,10-diene 在 三甲基氯硅烷 、 四溴环己二烯-1-酮 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 (2RS,3RS,5SR)-(1(SR)-bromo-heptyl)-3-chloro-2-hexyl-tetrahydro-furan
  参考文献：
  名称：

  A Biosynthetically-Inspired Synthesis of the Tetrahydrofuran Core of Obtusallenes II and IV

  摘要：

  Sharpless asymmetric dihydroxylation was regioselective for the trans olefin in an E vs Z vs terminal triene substrate. To test a biosynthetic hypothesis, the resulting diol underwent diastereoselective bromoetherification to provide the des-chloro core of marine natural products obtusallenes II and IV. Alternatively, anionic chloride ring-opening of a Z-beta,gamma-unsaturated epoxide gave separable regioisomeric halohydrins. Bromoetherification gave the fully elaborated core of obtusallenes II and IV with all of the relative stereochemistry correctly set.

  DOI：

  10.1021/ol062818g
• 作为产物：
  描述：

  庚醛 、 1,3-bis(triphenylphosphino)propane dibromide 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 以96%的产率得到(Z,Z)-heptadeca-7,10-diene
  参考文献：
  名称：

  A Biosynthetically-Inspired Synthesis of the Tetrahydrofuran Core of Obtusallenes II and IV

  摘要：

  Sharpless asymmetric dihydroxylation was regioselective for the trans olefin in an E vs Z vs terminal triene substrate. To test a biosynthetic hypothesis, the resulting diol underwent diastereoselective bromoetherification to provide the des-chloro core of marine natural products obtusallenes II and IV. Alternatively, anionic chloride ring-opening of a Z-beta,gamma-unsaturated epoxide gave separable regioisomeric halohydrins. Bromoetherification gave the fully elaborated core of obtusallenes II and IV with all of the relative stereochemistry correctly set.

  DOI：

  10.1021/ol062818g

文献信息

• Highly Efficient One-Pot Double-Wittig Approach to Unsymmetrical (1Z,4Z,7Z)-Homoconjugated Trienes
  作者：Georg Pohnert、Wilhelm Boland

  DOI：10.1002/(sici)1099-0690(200005)2000:9<1821::aid-ejoc1821>3.0.co;2-u

  日期：2000.5

  (Z)-hex-3-ene-1,6-bis(triphenylphosphonium iodide) (2) as key reagent. Double alkenylation of the corresponding bis(ylide) 3 with sequentially added aldehydes gives (Z)-1,4,7-homoconjugated trienes in good yields. Dissymmetrization of the bis(ylide) 3 is feasible, since it displays enhanced reactivity compared to the monoylide resulting from the first olefination. Symmetrical products from statistical coupling

  我们描述了一种使用对称 (Z)-hex-3-ene-1,6-bis(triphenylphosphonium iodide) (2) 作为关键试剂的针对不对称取代的跳过三烯的新型单锅双 Wittig 方法。相应的双(叶立德) 3 与依次添加的醛的双链烯基化以良好的产率得到 (Z)-1,4,7-同共轭三烯。双(叶立德) 3 的不对称化是可行的，因为与第一次烯化产生的单叶立德相比，它显示出增强的反应性。双(叶立德) 3 统计偶联的对称产物可以通过中间铝酸盐复合物的原位热分解缓慢释放第一个醛组分来显着抑制，中间铝酸盐复合物是通过用 DIBAL-H 还原甲酯生成的。该新策略已成功应用于功能化和同位素标记的多不饱和脂肪酸的一锅法合成以及测地虫信息素 (3Z,6Z,9Z)-nonadeca-1,3,6,9-tetraene 的合成(6a)。还发现不对称化策略适用于从 1,3-丙基双（三苯基溴化鏻）合成同共轭二烯。
• A Biosynthetically-Inspired Synthesis of the Tetrahydrofuran Core of Obtusallenes II and IV
  作者：D. Christopher Braddock、Roshni Bhuva、David S. Millan、Yolanda Pérez-Fuertes、Craig A. Roberts、Richard N. Sheppard、Savade Solanki、Elaine S. E. Stokes、Andrew J. P. White

  DOI：10.1021/ol062818g

  日期：2007.2.1

  Sharpless asymmetric dihydroxylation was regioselective for the trans olefin in an E vs Z vs terminal triene substrate. To test a biosynthetic hypothesis, the resulting diol underwent diastereoselective bromoetherification to provide the des-chloro core of marine natural products obtusallenes II and IV. Alternatively, anionic chloride ring-opening of a Z-beta,gamma-unsaturated epoxide gave separable regioisomeric halohydrins. Bromoetherification gave the fully elaborated core of obtusallenes II and IV with all of the relative stereochemistry correctly set.