1-bromo-7-hexadecyne | 676-35-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 1-bromo-7-hexadecyne
• 英文别名: 1-bromohexadec-7-yne；1-bromo-hexadec-7-yne；1-Brom-hexadec-7-in
• CAS: 676-35-7
• 化学式: C₁₆H₂₉Br
• 分子量: 301.31
• InChiKey: BKOYBCZNNLXIIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-bromo-7-hexadecyne 在 Lindlar catalyst N-甲基吗啉 、 盐酸 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 四丁基溴化铵 、 氢气 、 sodium hydride 、 三乙胺 、 氯甲酸甲酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 、 苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 生成 3-<(7Z)-hexadecenyl>-4-methylfuran-2,5-dione
  参考文献：
  名称：

  通过新的琥珀酸酯到马来酸酯的氧化反应，合成全合成Chaetomellic酸酐A和B。

  摘要：

  DOI：

  10.1021/jo9601977
• 作为产物：
  描述：

  7-十六炔酸 在 吡啶 、 lithium aluminium tetrahydride 、 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 1-bromo-7-hexadecyne
  参考文献：
  名称：

  164.长链酸的合成。第六部分 乙炔酸和顺式，顺式-docosa-5,13-二烯酸

  摘要：

  DOI：

  10.1039/jr9650000894

文献信息

• Isomerization of acetylenic acids with sodium salt of 1,2-diaminoethane: a one step synthesis of megatomoic acid
  作者：S. R. Abrams

  DOI：10.1139/v82-182

  日期：1982.5.15

  isomeric tetradecynoic acids were isomerized with the sodium salt of 1,2-diaminoethane. Isomers having the triple bond near the carboxyl group rearranged to E,Z-3,5- and E,E-3,5-tetradecadienoic acids (1 and 2), the former compound being the sex pheromone of the black carpet beetle. Isomers having the triple bond closer to the terminus of the chain afforded some 13-tetradecynoic acid along with 1 and 2

  许多异构的十四烷酸与 1,2-二氨基乙烷的钠盐异构化。在羧基附近具有三键的异构体重排为 E,Z-3,5- 和 E,E-3,5-十四碳二烯酸（1 和 2），前一种化合物是黑地毯甲虫的性信息素。具有更靠近链末端的三键的异构体与 1 和 2 一起提供了一些 13-十四烷酸。认为离域阴离子 12 和 13 有助于形成 1 和 2。
• Synthesis and biological activity of alkynoic acids derivatives against mycobacteria
  作者：Catherine Vilchèze、Lawrence W. Leung、Robert Bittman、William R. Jacobs Jr.

  DOI：10.1016/j.chemphyslip.2015.08.001

  日期：2016.1

  2-Alkynoic acids have bactericidal activity against Mycobacterium smegmatis but their activity fall sharply as the length of the carbon chain increased. In this study, derivatives of 2-alkynoic acids were synthesized and tested against fast- and slow-growing mycobacteria. Their activity was first evaluated in M. smegmatis against their parental 2-alkynoic acids, as well as isoniazid, a first-line antituberculosis drug. The introduction of additional unsaturation or heteroatoms into the carbon chain enhanced the antimycobacterial activity of longer chain alkynoic acids (more than 19 carbons long). In contrast, although the modification of the carboxylic group did not improve the antimycobacterial activity, it significantly reduced the toxicity of the compounds against eukaryotic cells. Importantly, 4-(alkylthio) but-2-ynoic acids, had better bactericidal activity than the parental 2-alkynoic acids and on a par with isoniazid against the slow-grower Mycobacterium bovis BCG. These compounds had also low toxicity against eukaryotic cells, suggesting that they could be potential therapeutic agents against other types of topical mycobacterial infections causing skin diseases including Mycobacterium abscessus, Mycobacterium ulcerans, and Mycobacterium leprae. Moreover, they provide a possible scaffold for future drug development. (C) 2015 Elsevier Ireland Ltd. All rights reserved.
• Probing structure/affinity relationships for the Plasmodium falciparum hexose transporter with glucose derivatives
  作者：Martine Fayolle、Marina Ionita、Sanjeev Krishna、Christophe Morin、Asha Parbhu Patel

  DOI：10.1016/j.bmcl.2005.11.068

  日期：2006.3

  A series of 3-O-substituted glucose derivatives was prepared with alkyl, alkenyl, aromatic and ferrocenic substituents; to vary lipophilicity and hydrogen bonding ethylenedioxy and perfluorinated fragments were also introduced. Apparent affinities for the Plasmodium falciparum hexose transporter (PfHT) were determined after heterologous expression in Xenopus oocytes, with highest affinities for compounds with C8-C13 lipophilic chains. As no derivatives show significant affinity for the mammalian glucose transporter (GLUT1), these structure/affinity assays contribute to design of potent PfHT inhibitors and eventual development of antimalarials. (C) 2005 Elsevier Ltd. All rights reserved.
• Tuning Packing and Solubility of Donor (D)–Acceptor (A) Polymers by <i>cis</i>–<i>trans</i> Isomerization within Alkenyl Side Chains
  作者：Felix Hinkel、Tomasz Marszalek、Wojciech Zajaczkowski、Sreenivasa Reddy Puniredd、Martin Baumgarten、Wojciech Pisula、Klaus Müllen

  DOI：10.1021/cm5021355

  日期：2014.8.26