3,5-octadiyn-1-ol | 10160-11-9

• 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: 3,5-octadiyn-1-ol
• 英文别名: Octa-3,5-diyn-1-OL
• CAS: 10160-11-9
• 化学式: C₈H₁₀O
• 分子量: 122.167
• InChiKey: YFBFKTPUNNZYIE-UHFFFAOYSA-N

物化性质

• 沸点：
  86-89 °C(Press: 0.2 Torr)
• 密度：
  0.979±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3,5-octadiyn-1-ol 在 氢氧化钾 、 锌铜偶 、 dilithium tetrachlorocuprate 、 三氯化铁 、 magnesium 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 19.5h， 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：

  1-溴-1-丁烷 、 3-丁炔-1-醇 在 copper(l) iodide 、 盐酸羟胺 、 二乙胺 作用下， 反应 2.5h， 以75%的产率得到3,5-octadiyn-1-ol
  参考文献：
  名称：

  Iwamoto, Minoru; Tagaki, Yoshikazu; Kogami, Kunio, Agricultural and Biological Chemistry, 1983, vol. 47, # 1, p. 117 - 120

  摘要：

  DOI：

文献信息

• Synthesis of the grapevine moth sex pheromone by Grignard?Schlosser cross-coupling: The effect of the electrophile structure on the stereoisomeric ratio in the reaction products
  作者：Z. G. Chrelashvili、M. V. Mavrov、A. V. Dolidze、A. O. Chizhov、E. P. Serebryakov

  DOI：10.1007/bf00704206

  日期：1993.6

  Abstract1-Acetoxy-2E,4Z-heptadiene (4) and 1-bromo-3E,5Z-octadiene (5) were obtained with ≥90 and 88–92 % configurational purity, respectively, starting from 2,4-heptadiyn-1-ol or 3,5-octadiyn-1-ol. The Li2CuCl4-catalyzed cross-coupling of the allylic acetate4 with 5tert-butoxypentylmagnesium chloride affords 1-tert-butoxy-7E,9Z-dodecadiene (11) contaminated with ≥25 % of minor stereoisomers in 54–60

  摘要 1-Acetoxy-2E,4Z-heptadiene (4) 和 1-bromo-3E,5Z-octadiene (5) 从 2,4-heptadiyn-1- 开始分别获得了≥90 和 88-92% 的构型纯度ol 或 3,5-octadiyn-1-ol。Li2CuCl4 催化的乙酸烯丙酯 4 与 5-叔丁氧基戊基氯化镁的交叉偶联得到 1-叔丁氧基-7E,9Z-十二二烯 (11)，其被 ≥25% 的次要立体异构体污染，总产率为 54-60%。在类似的条件下，高烯丙基溴 5 与 4-叔丁氧基丁基氯化镁反应，产生 50-52% 的二烯 11 样品，其中含有≤17% 的次要立体异构体。如果后一种偶联是用烯炔 8 而不是 5 进行的，然后对所得产物中的三键进行顺式氢化，则二烯 11 的构型纯度高达 84.7%（总产率约为 45%）。
• 13-Acetoxy-heptadecadien-(8, 10)-ol-(1), Octadien-(3, 5)-ol-(1)-Isomere und verwandte Verbindungen
  作者：R. Riemschneider、G. Kasang、C. Böhme

  DOI：10.1007/bf01185898

  日期：1965.11
• Synthesis of 7E,9Z-dodecadienyl acetate, the sex pheromone ofLobesia botrana Shiff
  作者：Z. G. Chrelashvili、M. V. Mavrov、A. V. Dolidze、A. P. Voronkov、E. P. Serebryakov

  DOI：10.1007/bf00704016

  日期：1993.4

  Two syntheses of 7E,9Z-dodecadienyl acetate from 1,3-butadiyne were carried out using either 2E,4Z-heptadienyl acetate or 1-bromo-3E,5Z-octadiene as the key intermediates, The latter underwent organocopper cross-coupling with the respective complementary Grignard reagents (prepared from the corresponding 1-tert-butoxy-omega-chlorohydrins) as alkylating agents.
• US9163307B2
  申请人：——

  公开号：US9163307B2

  公开（公告）日：2015-10-20
• 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.