dodeca-3,5-diyn-1-ol | 165550-73-2

• 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: dodeca-3,5-diyn-1-ol
• CAS: 165550-73-2
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: AGXZPVYGNBXELN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  dodeca-3,5-diyn-1-ol 在 sodium hydroxide 、 bis(cyclohexanyl)borane 、 双氧水 作用下， 以 吡啶 为溶剂， 反应 5.5h， 生成 (3E,5Z)-dodeca-3,5-dien-1-yl acetate
  参考文献：
  名称：

  Synthesis and Characterization of the Four Geometrical Isomers of 3,5-Dodecadienyl Acetate.

  摘要：

  Practical convergent syntheses of the four geometrical isomers of 3,5-dodecadienyl acetate are presented. These substances have been characterized by NMR and mass spectroscopy. (3E,5Z)-3,5-Dodecadienyl acetate is the main female sex pheromone component of the leaf roller Bonagota cranaodes, which is an important insect pest in apples in South America.The isomeric 3,5-dodecadienyl acetates, as pure isomers and in defined mixtures, have been used as trap lures for Eying insects in field screening experiments in Lithuania. Although no insects were found in the control traps, the numbers of males caught in the baited traps were not high enough to be statistically significant.

  DOI：

  10.3891/acta.chem.scand.52-0930
• 作为产物：
  描述：

  庚醛 在 哌啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 dodeca-3,5-diyn-1-ol
  参考文献：
  名称：

  共轭烯炔醇/胺的化学，区域和立体选择性氢硼化：带有羟基/氨基的Z，Z- / Z，E -1,3-dien-1 / 2-基硼酸酯的轻松合成

  摘要：

  分别以铜盐和双（频哪醇）二硼为预催化剂和硼源研究了共轭烯炔醇/胺的硼氢化反应。建议化学选择性源自基质上杂原子和过渡金属上配体的综合电子影响。区域选择性可能主要由炔烃取代基的电子效应决定。这项研究导致了访问带有羟基/氨基的Z，Z- / Z，E -1,3-dien-1 / 2-ylboronic酯的高选择性方案。

  DOI：

  10.1016/j.tetlet.2016.05.075

文献信息

• Copper-Catalyzed Cross-Coupling Reactions of Bromoalkynols with Terminal Alkynes in Supercritical Carbon Dioxide
  作者：Huan-Feng Jiang、A-Zhong Wang

  DOI：10.1055/s-2007-966058

  日期：2007.6

  Copper-catalyzed cross-coupling reactions of bromo-alkynols and terminal alkynes were carried out in supercritical carbon dioxide (scCO 2 ) to afford the corresponding unsymmetrical diynes with good yields. The reaction is sensitive to temperature and the pressure of CO 2 . Methanol, as a cosolvent of scCO 2 , could promote dissolution of the inorganic salt and thus facilitated the reaction. This new heterocoupling

  溴代炔醇和末端炔烃的铜催化交叉偶联反应在超临界二氧化碳（scCO 2 ）中进行，以良好的收率得到相应的不对称二炔。该反应对CO 2 的温度和压力敏感。甲醇作为scCO 2 的助溶剂，可以促进无机盐的溶解，从而促进反应。这种新的异质偶联反应系统比更传统的方法更环保，因为它使用 scCO 2 作为溶剂，乙酸钠作为碱而不是胺。
• The polymer-supported Cadiot-Chodkiewicz coupling of acetylenes to produce unsymmetrical diynes
  作者：John M. Montierth、Dierdre R. DeMario、Mark J. Kurth、Neil E. Schore

  DOI：10.1016/s0040-4020(98)83035-4

  日期：1998.9

  Cu(II)-catalyzed coupling of polymer-bound ω-haloalkyn-l-ols to terminal alkynes proceeds in moderate yield to give unsymmetrical diynes upon hydrolytic removal from the polymer. Formation of the symmetrical homocoupled byproduct is suppressed relative to conventional Cadiot-Chodkiewicz conditions in homogeneous solution.

  Cu（II）催化的与聚合物结合的ω-卤代炔-1-醇与末端炔烃的偶联以中等收率进行，从聚合物中水解除去后，得到不对称的二炔。相对于传统的Cadiot-Chodkiewicz条件，在均质溶液中，对称的均质偶合副产物的形成受到抑制。
• A convenient route to unsymmetrical conjugated diynes
  作者：Mouâd Alami、Fabiola Ferri

  DOI：10.1016/0040-4039(96)00414-5

  日期：1996.4

  Various unsymmetrical conjugated diynes can be prepared in good to excellent isolated yields by copper catalyzed coupling reaction of terminal alkynes with 1-iodo alkynes in pyrrolidine. In the case of 1-bromo alkynes, the presence of a catalytic amount of PdCl2(PPh3)2 improved the yield of coupling products.

  通过在末端的炔烃与吡咯烷中的1-碘炔烃进行铜催化的偶合反应，可以制备出各种良好的分离收率的非对称共轭二炔。在1-溴炔烃的情况下，催化量的PdCl 2（PPh 3）2的存在提高了偶联产物的产率。
• Effects of Structural Variations on Antibacterial Properties for Conjugated Diynes Generated through Glaser Hay Couplings
  作者：Emma A. Hale、Hannah M. Ryan、Alexandra M. McOsker、Cody M. Funk、Lauren C. Green、Lauren E. Mazur、Diya M. Uthappa、Brian M. Flood、Douglas D. Young、Robert J. Hinkle

  DOI：10.1002/cmdc.202200455

  日期：2022.12.16

  A series of conjugated diynes were prepared via both solution phase and solid-supported Glaser Hay couplings and screened for selective antibacterial activities. A focused structure–activity relationship screen was performed to identify key components of natural product derivatives that were essential for biological activity.

  通过溶液相和固载 Glaser Hay 偶联制备了一系列共轭二炔，并筛选了其选择性抗菌活性。进行了重点结构-活性关系筛选，以确定对生物活性至关重要的天然产物衍生物的关键成分。
• Balova; Morozkina; Voskresenskii, Russian Journal of Organic Chemistry, 2000, vol. 36, # 10, p. 1428 - 1436
  作者：Balova、Morozkina、Voskresenskii、Remizova

  DOI：——

  日期：——