辛-5,7-二炔-1-醇 | 141682-12-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 辛-5,7-二炔-1-醇
• 英文名称: octa-5,7-diyn-1-ol
• 英文别名: 5,7-Octadiyn-1-ol
• CAS: 141682-12-4
• 化学式: C₈H₁₀O
• 分子量: 122.167
• InChiKey: MUPPZGZHSCECDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  4
• 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：

  辛-5,7-二炔-1-醇 在 咪唑 、 N,N-diisopropanolamine 、 trans-bis(triphenylphosphine)palladium dichloride 、 tetra-n-butylammoniumfluoride trihydrate 、 四丁基氟化铵 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 methyl 2,3-di(hex-5-en-1-yn-1-yl)-1-methyl-1H-indole-5-carboxylate
  参考文献：
  名称：

  芳基乙炔在杂环核中的官能化对映体的合成中的亲电子环化反应

  摘要：

  开发了一种有效的策略，用于合成与苯并噻吩，苯并呋喃和吲哚稠合的不对称取代烯二炔。所提出的方法基于联乙炔的亲电环化和Sonogashira偶联。因此，易得邻位的碘环化-官能化的（buta-1,3-diynyl）芳烃被用作合成2-ethynyl-3-iodoheteroindeness的直接方法。这些底物及其修饰的衍生物很容易通过Sonogashira与乙炔的偶合转化为稠合到杂环上的各种不对称取代的无环烯二炔。所开发的方法对各种官能团的耐受性是在稠合至杂环核心的大环烯二炔系统合成中的巨大优势。以闭环复分解为关键步骤，完成了吲哚稠合的12元大环二烯二炔的合成。

  DOI：

  10.1021/jo501396s
• 作为产物：
  描述：

  pentynyl bromide 在 盐酸羟胺 、 lithium 、 乙二胺 、 正丁胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 乙醇 、 六氯-1,3-丁二烯 、 甲苯 为溶剂， 反应 0.58h， 生成 辛-5,7-二炔-1-醇
  参考文献：
  名称：

  芳基乙炔在杂环核中的官能化对映体的合成中的亲电子环化反应

  摘要：

  开发了一种有效的策略，用于合成与苯并噻吩，苯并呋喃和吲哚稠合的不对称取代烯二炔。所提出的方法基于联乙炔的亲电环化和Sonogashira偶联。因此，易得邻位的碘环化-官能化的（buta-1,3-diynyl）芳烃被用作合成2-ethynyl-3-iodoheteroindeness的直接方法。这些底物及其修饰的衍生物很容易通过Sonogashira与乙炔的偶合转化为稠合到杂环上的各种不对称取代的无环烯二炔。所开发的方法对各种官能团的耐受性是在稠合至杂环核心的大环烯二炔系统合成中的巨大优势。以闭环复分解为关键步骤，完成了吲哚稠合的12元大环二烯二炔的合成。

  DOI：

  10.1021/jo501396s

文献信息

• [EN] CONJUGATED UNSATURATED COMPOUNDS<br/>[FR] COMPOSÉS INSATURÉS CONJUGUÉS
  申请人：COMMW SCIENT IND RES ORG

  公开号：WO2009111830A1

  公开（公告）日：2009-09-17

  The present invention relates to a class of conjugated unsaturated compounds, to a method of preparing such compounds, and to the polymerisation and bio-active uses of such compounds including their use as antimicrobial agents. The invention particularly relates to compounds containing three conjugated unsaturated moieties, at least two of which are yne moieties.

  本发明涉及一类共轭不饱和化合物，涉及制备这类化合物的方法，以及这类化合物的聚合和生物活性用途，包括它们作为抗微生物剂的用途。该发明特别涉及含有三个共轭不饱和基团的化合物，其中至少有两个是炔基团。
• Synthesis and Solid-State Polymerization of Triyne and Enediyne Derivatives with Similar π-Conjugated Structures
  作者：Kana Mizukoshi、Shuji Okada、Tatsumi Kimura、Satoru Shimada、Hiro Matsuda

  DOI：10.1246/bcsj.81.1028

  日期：2008.8.15

  Three diacetylene monomer model compounds with similar π-conjugation systems, 10-phenyl-5,7,9-decatriynyl N-phenylcarbamate (1), (E)-10-phenyldec-9-en-5,7-diynyl N-phenylcarbamate (2), and (E)-10-phenyldec-5-en-7,9-diynyl N-phenylcarbamate (3), were synthesized and their properties and solid-state polymerization were investigated. Based on the absorption spectra of the monomers, it was found that the conjugation effect of a double bond was different from that of a triple bond in solution. Monomers 1, 2, and 3 gave one, two, and five crystal forms, respectively, of which 1 and one of the crystal forms of 2 (2a) could be polymerized in the solid state. The conversions after γ-ray irradiation (1 MGy dose) were 53% and 20%, respectively. The longest-wavelength absorption maxima of the polymers prepared from 1 and 2a were 645 and 655 nm, respectively. The polymerizable crystals 1 and 2a were found to have layered monomer structures with spacing of 3.1–3.6 nm. Based on solid-state 13C NMR spectra, the polymerization sites of 1 were determined to be the 1,4- and 3,6-positions with respect to the phenyl ring, and that of 2a was determined to be the 3,6-position with respect to the phenyl ring.

  合成了三种具有相似π-共轭体系的二乙炔单体模型化合物，即10-苯基-5,7,9-十碳三炔基N-苯基氨基甲酸酯（1）、（E）-10-苯基-9-十碳烯-5,7-二炔基N-苯基氨基甲酸酯（2）和（E）-10-苯基-5-十碳烯-7,9-二炔基N-苯基氨基甲酸酯（3），并研究了它们的性质和固态聚合性。根据单体的吸收光谱，发现溶液中双键的共轭效应与三键不同。单体1、2和3分别呈现一种、两种和五种晶型，其中单体1和单体2的一种晶型（2a）可以在固态下聚合。经过γ射线辐照（剂量为1 MGy）后，转化率分别为53%和20%。由单体1和2a制备的聚合物的最长波长吸收最大值分别为645 nm和655 nm。可聚合的晶体1和2a被发现具有层状单体结构，间距为3.1-3.6 nm。根据固态13C NMR光谱，确定了单体1的聚合位点为苯环的1,4-和3,6-位，单体2a的聚合位点为苯环的3,6-位。
• Functionalized buta-1,3-diynyl- N -methylpyrazoles by sequential “diacetylene zipper” and Sonogashira coupling reactions
  作者：Anastasiya I. Govdi、Alexandra E. Kulyashova、Sergey F. Vasilevsky、Irina A. Balova

  DOI：10.1016/j.tetlet.2017.01.032

  日期：2017.2

  A reaction sequence consisting of the “Diacetylene zipper” of buta-1,3-diynes from internal to terminal isomers, followed by Sonogashira cross-coupling with 3-,4- or 5-iodopyrazoles, was investigated as a new approach to buta-1,3-diynyl-N-methylpyrazoles. Various pyrazoles bearing alkyl and hydroxyalkyl containing buta-1,3-diyne substituents in the 3-,4- or 5-position and functional groups at the neighboring

  研究了由内部异构体到末端异构体的Buta-1,3-diynes的“二乙炔拉链”，然后将Sonogashira与3-，4-或5-碘吡唑交叉偶联的反应顺序，是一种新的Buta- 1,3-二炔基-N-甲基吡唑。得到了各种带有在3-，4-或5-位上含有buta-1，3-diyne取代基和在环的相邻位置上具有官能团的烷基和羟烷基的吡唑。
• Synthesis and solid-state polymerization of monomers with a conjugated diyne–triene–diyne structure
  作者：Kazumasa Higuchi、Keita Sasamura、Kei Mizuguchi、Yoko Tatewaki、Shuji Okada

  DOI：10.1016/j.polymer.2013.04.018

  日期：2013.5

  diyne–triene–diyne structure were synthesized and their solid-state polymerization was investigated for the first time. The monomers could be polymerized by UV irradiation at 254 nm or 365 nm and increase of the absorption in the visible region was observed during polymerization. Since the absorption tail of the photoproducts shifted to longer wavelength than that of the corresponding monomers, the main photoreaction

  合成具有共轭二炔-三烯-二炔结构的Tetradeca-5,7,9-三烯-1,3,11,13-四炔衍生物，并对其固态聚合进行了首次研究。可以通过在254nm或365nm处的UV辐射使单体聚合，并且在聚合过程中观察到在可见光区域吸收的增加。由于光产物的吸收尾移到比相应单体的吸收尾更长的波长，因此估计聚合初期的主要光反应方案为在二炔部分中的1,4-加成。然而，没有观察到具有规则结构的聚二乙炔的激子吸收带。通过粉末X射线衍射确认的结晶度在光聚合过程中损失，并且发现聚合物无序。
• Synthesis and activity of polyacetylene substituted 2-hydroxy acids, esters, and amides against microbes of clinical importance
  作者：Stella Kyi、Nalin Wongkattiya、Andrew C. Warden、Michael S. O’Shea、Margaret Deighton、Ian Macreadie、Florian H.M. Graichen

  DOI：10.1016/j.bmcl.2010.06.020

  日期：2010.8

  A series of novel polyacetylene substituted 2-hydroxy acids and derivatives were prepared and characterized. Alkylation of butane-2,3-diacetal (BDA) protected glycolic acid with iodoalkyl substituted polyacetylene compounds gave the corresponding diacetal protected polyacetylene substituted 2-hydroxy acids. Diacetal deprotection through acid mediated hydrolysis, transesterification or aminolysis afforded the 2-hydroxy-polyacetylenic acid, ester or amide derivatives. Twenty one of these novel compounds were tested against 10 microbes of clinical importance and several of them showed good antimicrobial activity, in particular against Pseudomonas aeruginosa. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.