pentadeca-2,4-diyn-1-ol | 139060-06-3

• 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: pentadeca-2,4-diyn-1-ol
• CAS: 139060-06-3
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: XVCFFTARIUIEGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  pentadeca-2,4-diyn-1-ol 在 吡啶 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以77%的产率得到1-chloropentadeca-2,4-diyne
  参考文献：
  名称：

  Synthesis of novel amphiphilic diacetylenes with amino or ammonium functionality

  摘要：

  An optimized procedure for the Cadiot-Chodkiewicz coupling of mono- and dipropargylamines with iodododecyne to yield the diynylamines bis(pentadeca-2,4-diyn-1-yl)amine (1) and pentadeca-2,4-diyn-1-ylamine (3) is given. The amines were converted in good yields into the corresponding amphiphilic quaternary ammonium salts dimethylbis(pentadeca-2,4-diyn-1-yl)ammonium iodide (7) and trimethylpentadeca-2,4-diyn-1-ylammonium iodide (8).

  DOI：

  10.1016/s0040-4020(01)80730-4
• 作为产物：
  描述：

  1-碘十二碳-1-炔 、 2-丙炔-1-醇 在 copper(l) chloride 盐酸羟胺 、 乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以77%的产率得到pentadeca-2,4-diyn-1-ol
  参考文献：
  名称：

  Synthesis of novel amphiphilic diacetylenes with amino or ammonium functionality

  摘要：

  An optimized procedure for the Cadiot-Chodkiewicz coupling of mono- and dipropargylamines with iodododecyne to yield the diynylamines bis(pentadeca-2,4-diyn-1-yl)amine (1) and pentadeca-2,4-diyn-1-ylamine (3) is given. The amines were converted in good yields into the corresponding amphiphilic quaternary ammonium salts dimethylbis(pentadeca-2,4-diyn-1-yl)ammonium iodide (7) and trimethylpentadeca-2,4-diyn-1-ylammonium iodide (8).

  DOI：

  10.1016/s0040-4020(01)80730-4

文献信息

• Synthesis and Cytotoxic Activity of a Series of Diacetylenic Compounds Related to Falcarindiol.
  作者：William N. SETZER、Xuyuan GU、Eric B. WELLS、Mary C. SETZER、Debra M. MORIARITY

  DOI：10.1248/cpb.48.1776

  日期：——

  The synthesis of a series of diacetylenic compounds related to the natural product falcarindiol has been carried out. Unsymmetrical diacetylenes were prepared by a modification of the Cadiot-Chodkiewicz coupling reaction, while a Glaser coupling was used to prepare symmetrical diacetylenes. These compounds have been tested for in vitro cytotoxic activity against Hep-G2, and H-4-II-E cell lines. Diacetylenes

  已经进行了一系列与天然产物falcarindiol有关的二炔化合物的合成。通过修饰Cadiot-Chodkiewicz偶联反应制备不对称的二乙炔，而使用Glaser偶联制备对称的二乙炔。已经测试了这些化合物对Hep-G2和H-4-II-E细胞系的体外细胞毒活性。在C-1、2具有额外的不饱和键并在C-3和C-8带有羟基或具有长疏水链的联乙炔的IC50值在微摩尔范围内。
• An Atom-Economic and Selective Ruthenium-Catalyzed Redox Isomerization of Propargylic Alcohols. An Efficient Strategy for the Synthesis of Leukotrienes
  作者：Barry M. Trost、Robert C. Livingston

  DOI：10.1021/ja804105m

  日期：2008.9.10

  secondary propargylic alcohols in good yields to provide trans enals and enones exclusively. Readily available indenylbis(triphenylphosphine)ruthenium chloride, in the presence of indium triflate and camphorsulfonic acid, gives the best turnover numbers and reactivity with the broadest range of substrates. Deuterium labeling experiments suggest that the process occurs through propargylic hydride migration

  催化钌配合物与铟助催化剂和布朗斯台德酸一起以良好的产率异构化伯醇和仲炔醇，以专门提供反式烯醛和烯酮。在三氟甲磺酸铟和樟脑磺酸存在下，现成的茚基双（三苯基膦）氯化钌可提供最佳的转化率和对最广泛底物的反应性。氘标记实验表明，该过程是通过炔丙基氢化物迁移随后产生的乙烯基钌中间体的质子裂解发生的。这种方法在白三烯 B4 的合成中的应用证明了它的实用性和非凡的选择性。
• Cationic Amphiphiles Bearing a Diacetylenic Function in the Headgroup: Aggregative Properties and Polymerization
  作者：Alessandro Mauceri、Luisa Giansanti、Donatella Capitani、Anatoly Sobolev、Luciano Galantini、Mauro Bassetti、Maria Grazia Nemi、Denise Gradella Villalva、Sara Battista、Giovanna Mancini

  DOI：10.1021/acs.langmuir.0c01735

  日期：2020.10.20

  liposomes. Structurally related cationic diacetylenic amphiphiles featuring the conjugated triple bonds proximate to charged nitrogen were synthesized and evaluated in their ability to polymerize under aggregative conditions. The occurrence of polymerization only in certain aggregating conditions was rationalized by nuclear magnetic resonance (NMR) and Langmuir trough experiments.

  在二乙炔类脂的广阔全景中，光响应性共轭1,3-二炔功能通常包裹在两亲分子的烃链中，与头基的距离可变。因此，通过利用相应的脂质体在紫外线照射下聚合获得的聚二乙炔网络，被用作传感功能，被嵌入脂质体的疏水区域。合成了结构相关的阳离子二炔两亲物，其特征在于靠近带电氮的共轭三键，​​并评估了它们在聚合条件下聚合的能力。通过核磁共振（NMR）和朗缪尔（Langmuir）槽实验，合理地解释了仅在某些聚集条件下发生的聚合反应。
• New irreversible thermochromic polydiacetylenes
  作者：Laurent Rougeau、Dominique Picq、Marie Rastello、Yves Frantz

  DOI：10.1016/j.tet.2008.07.085

  日期：2008.9

  New diacetylenic compounds are described. These compounds are unfunctionalised, monoalcohols, diols or monoesters and present irreversible thermochromic behaviour. When heated, these diynes change colour from blue to red in temperature ranging between −50 and +75 °C depending on chain lengths. A relationship between the number of atoms and the thermochromism temperature has been highlighted. Moreover

  描述了新的二炔化合物。这些化合物是未官能化的一元醇，二醇或单酯，具有不可逆的热致变色行为。加热时，这些二炔根据链长的不同，在−50至+75°C的温度范围内从蓝色变为红色。原子数与热致变色温度之间的关系已被强调。此外，基于拉曼光谱，ESR和固体NMR证明了该热致变色现象的机理。
• 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。