(2Z,4Z)-2,4-heptadien-1-ol | 179331-78-3

• 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: (2Z,4Z)-2,4-heptadien-1-ol
• 英文别名: (2Z,4Z)-hepta-2,4-dien-1-ol
• CAS: 179331-78-3
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: MDRZSADXFOPYOC-OUPQRBNQSA-N

物化性质

• 沸点：
  176.8±9.0 °C(Predicted)
• 密度：
  0.870±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2Z,4Z)-2,4-heptadien-1-ol 在 4-二甲氨基吡啶 、 dilithium tetrachlorocuprate 、 三氯化铁 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 30.0h， 生成 (E,Z)-7,9-dodecadienyl acetate
  参考文献：
  名称：

  Synthesis of (7Z,9Z)-dodecadienyi acetate, a component of sex pheromones of the leafrollersEpinotia andEucosma, using conjugated diynols

  摘要：

  Two analogous routes to the title pheromones were elaborated based on organocuprate cross-coupling of Z,Z-dienic electrophiles, (2Z,4Z)-1-acetoxy-2,4-heptadiene (6) and (3Z,5Z)-1-bromoctadiene (8), with omega-tert-butoxy-1-chloropentane and -butane, respectively. Optimal conditions for the reduction of 2,4-heptadiyn-1-ol and 3,5-octadiyn-1-ol to the respective Z,Z-alkadienols as precursors for the electrophiles were found. Treatment of diynols with activated zinc in aqueous alcohol provided high geometrical purity of the product (greater-than-or-equal-to 94 %). In both cases, copper-catalyzed cross-coupling afforded 1-tert-butoxy-7,9-dodecadiene (four stereoisomers), acetolysis of which gave the target pheromone contaminated by stereoisomers. In the case of allylic electrophile 6, the reaction occurred with the loss of the initial configurational purity, whereas the use of homoallylic bromide 8 ensured almost complete retention of the configuration of the double bonds and obtaining the target pheromone of 87 % configurational purity.

  DOI：

  10.1007/bf00699203
• 作为产物：
  描述：

  2,4-庚二炔-1-醇 在 锌铜偶 作用下， 以 水 、 异丙醇 为溶剂， 反应 4.0h， 以56%的产率得到(2Z,4Z)-2,4-heptadien-1-ol
  参考文献：
  名称：

  Synthesis of (7Z,9Z)-dodecadienyi acetate, a component of sex pheromones of the leafrollersEpinotia andEucosma, using conjugated diynols

  摘要：

  Two analogous routes to the title pheromones were elaborated based on organocuprate cross-coupling of Z,Z-dienic electrophiles, (2Z,4Z)-1-acetoxy-2,4-heptadiene (6) and (3Z,5Z)-1-bromoctadiene (8), with omega-tert-butoxy-1-chloropentane and -butane, respectively. Optimal conditions for the reduction of 2,4-heptadiyn-1-ol and 3,5-octadiyn-1-ol to the respective Z,Z-alkadienols as precursors for the electrophiles were found. Treatment of diynols with activated zinc in aqueous alcohol provided high geometrical purity of the product (greater-than-or-equal-to 94 %). In both cases, copper-catalyzed cross-coupling afforded 1-tert-butoxy-7,9-dodecadiene (four stereoisomers), acetolysis of which gave the target pheromone contaminated by stereoisomers. In the case of allylic electrophile 6, the reaction occurred with the loss of the initial configurational purity, whereas the use of homoallylic bromide 8 ensured almost complete retention of the configuration of the double bonds and obtaining the target pheromone of 87 % configurational purity.

  DOI：

  10.1007/bf00699203

文献信息

• [EN] BIARYL COMPOSITIONS AND METHODS FOR MODULATING A KINASE CASCADE<br/>[FR] COMPOSITIONS DE BIARYLE ET PROCÉDÉS DE MODULATION D'UNE CASCADE DE KINASES
  申请人：KINEX PHARMACEUTICALS LLC

  公开号：WO2008127728A1

  公开（公告）日：2008-10-23

  [EN] The invention relates to compounds of formula IB and methods for modulating one or more components of a kinase cascade using these compounds.
  [FR] L'invention concerne des composés de formule IB et des procédés de modulation d'un ou plusieurs composants d'une cascade de kinases urilisant ces composés.
• [EN] ACTINIC-RAY- OR RADIATION-SENSITIVE RESIN COMPOSITION AND METHOD OF FORMING A PATTERN USING THE SAME<br/>[FR] COMPOSITION DE RÉSINE SENSIBLE AU RAYONNEMENT OU À DES RAYONS ACTINIQUES ET PROCÉDÉ DE FORMATION D'UN MOTIF AU MOYEN D'UNE TELLE COMPOSITION
  申请人：FUJIFILM CORP

  公开号：WO2011034213A1

  公开（公告）日：2011-03-24

  According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes a resin containing a repeating unit (A) containing both a structural moiety (S1) that is decomposed by an action of an acid to thereby generate an alkali-soluble group and a structural moiety (S2) that is decomposed by an action of an alkali developer to thereby increase its rate of dissolution into the alkali developer, and a compound that generates an acid when exposed to actinic rays or radiation.
• Synthesis of (7Z,9Z)-dodecadienyi acetate, a component of sex pheromones of the leafrollersEpinotia andEucosma, using conjugated diynols
  作者：Z. G. Chrelashvili、M. V. Mavrov、B. I. Ugrak、A. A. Kutin、E. P. Serebryakov

  DOI：10.1007/bf00699203

  日期：1993.9

  Two analogous routes to the title pheromones were elaborated based on organocuprate cross-coupling of Z,Z-dienic electrophiles, (2Z,4Z)-1-acetoxy-2,4-heptadiene (6) and (3Z,5Z)-1-bromoctadiene (8), with omega-tert-butoxy-1-chloropentane and -butane, respectively. Optimal conditions for the reduction of 2,4-heptadiyn-1-ol and 3,5-octadiyn-1-ol to the respective Z,Z-alkadienols as precursors for the electrophiles were found. Treatment of diynols with activated zinc in aqueous alcohol provided high geometrical purity of the product (greater-than-or-equal-to 94 %). In both cases, copper-catalyzed cross-coupling afforded 1-tert-butoxy-7,9-dodecadiene (four stereoisomers), acetolysis of which gave the target pheromone contaminated by stereoisomers. In the case of allylic electrophile 6, the reaction occurred with the loss of the initial configurational purity, whereas the use of homoallylic bromide 8 ensured almost complete retention of the configuration of the double bonds and obtaining the target pheromone of 87 % configurational purity.