1,16-二溴十六烷 | 45223-18-5

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类硝化物
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 中文名称: 1,16-二溴十六烷
• 英文名称: 1,16-dibromohexadecane
• CAS: 45223-18-5
• 化学式: C₁₆H₃₂Br₂
• mdl: MFCD00039195
• 分子量: 384.238
• InChiKey: OTFBUFWEFKVFFR-UHFFFAOYSA-N

物化性质

• 熔点：
  56.2-56.7 °C
• 沸点：
  397.8±10.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  18
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2903399090
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  2-8℃

制备方法与用途

用途

1,16-二溴十六烷是一种有机中间体，可通过将1,16-十六烷二醇进行溴代反应制得。

反应信息

• 作为反应物：
  描述：

  1,16-二溴十六烷 在 氢氧化钾 、 potassium ethoxide 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.67h， 生成 1-tosylazacycloheptadecane
  参考文献：
  名称：

  Gargano, Patrizia; Mandolini, Luigi, Gazzetta Chimica Italiana, 1982, vol. 112, # 1/2, p. 31 - 34

  摘要：

  DOI：
• 作为产物：
  描述：

  16-溴-1-十六烷醇 在 四溴化碳 、 三苯基膦 作用下， 以 乙醚 为溶剂， 以95%的产率得到1,16-二溴十六烷
  参考文献：
  名称：

  Conformationally-locked N-glycosides: Exploiting long-range non-glycone interactions in the design of pharmacological chaperones for Gaucher disease

  摘要：

  Pyranoid-type glycomimetics having a cis-1,2-fused glucopyranose-2-alkylsulfany1-1,3-oxazoline (Glc-PSO) structure exhibit an unprecedented specificity as inhibitors of mammalian beta-glucosidase. Notably, their inhibitory potency against human beta-glucocerebrosidase (GCase) was found to be strongly dependent on the nature of aglycone-type moieties attached at the sulfur atom. In the particular case of omega-substituted hexadecyl chains, an amazing influence of the terminal group was observed. A comparative study on a series of Glc-PSO derivatives suggests that hydrogen bond acceptor functionalities, e.g. fluoro or methyloxycarbonyl, significantly stabilize the Glc-PSO:GCase complex. The S-(16-fluorohexadecyl)-PSO glycomimetic turned out to be a more potent GCase competitive inhibitor than ambroxol, a non glycomimetic drug currently in pilot trials as a pharmacological chaperone for Gaucher disease. Moreover, the inhibition constant increased by one order of magnitude when shifting from neutral (pH 7) to acidic (pH 5) media, a favorable characteristic for a chaperone candidate. Indeed, the fluoro-PSO derivative also proved superior to ambroxol in mutant GCase activity enhancement assays in N370S/N370S Gaucher fibroblasts. The results presented here represent a proof of concept of the potential of exploiting long-range non-glycone interactions for the optimization of glycosidase inhibitors with chaperone activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.002

文献信息

• Nickel‐Catalyzed Inter‐ and Intramolecular Aryl Thioether Metathesis by Reversible Arylation
  作者：Tristan Delcaillau、Alessandro Bismuto、Zhong Lian、Bill Morandi

  DOI：10.1002/anie.201910436

  日期：2020.1.27

  A nickel-catalyzed aryl thioether metathesis has been developed to access high-value thioethers. 1,2-Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional-group-tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis that does not involve alkene bonds. In-depth organometallic

  已经开发出镍催化的芳基硫醚复分解反应来获得高价值的硫醚。1,2-双（二环己基膦基）乙烷（dcype）对于促进这种高度官能团耐受的反应至关重要。此外，在不涉及烯键的闭环易位的不寻常实例中，可以高收率获得具有合成挑战性的大环化合物。深入的有机金属研究支持产物形成的可逆Ni0 / NiII途径。总体而言，这项工作不仅为以前的基于Pd的催化体系提供了更可持续的替代方法，而且还提出了与异常单键易位反应的进一步开发和应用高度相关的新应用和机理信息。
• An Efficient Procedure for the 1-Alkylation of 2-Nitroimidazoles and the Synthesis of a Probe for Hypoxia in Solid Tumours
  作者：Anthony Long、John Parrick、Richard J. Hodgkiss

  DOI：10.1055/s-1991-26552

  日期：——

  The N-alkylation of 2-nitroimidazole through its 'naked' anion, formed from its alkali metal salts in the presence of crown ethers and in homogeneous solution, is shown to be a useful preparative procedure. The reactions of α,ω-dihaloalkanes can be controlled to afford either the mono- or diheteroarylalkane. The procedure has been used to alkylate theophylline and to prepare a compound of use as a probe to identify, locate and quantify hypoxia in sections from solid tumours.

  裸露阴离子形式的2-硝基咪唑的N-烷基化反应，通过其在冠醚存在下由碱金属盐形成的均相溶液中进行，已被证明是一种有用的制备方法。α,ω-二卤代烷的反应可以被调控，以获得单或双杂芳基烷。该方法已被用于碱基化茶碱，并制备了一种可作为探针的化合物，用于在固体肿瘤组织切片中鉴定、定位和量化缺氧区域。
• THE ELECTROLYSIS OF ω-BROMOCARBOXYLIC ACIDS
  作者：R.G. Woolford

  DOI：10.1139/v62-280

  日期：1962.9.1

  The first successful preparation of ω,ω′-dibromides from the electrolyses of a series of ω-bromocarboxylic acids, Br(CH₂)_nCOOH (n = 5 to n = 11), is reported. Under conditions of fairly low temperature and current density, yields from 54 to 71% of these dibromides were obtained.The electrolysis of 11-bromoundecanoic acid is discussed as an example of how a small change in experimental conditions can produce a considerable change in the products of reaction. At 50°, the product was mainly 1,20-dibromoeicosane, whereas at 65° the products were mainly the esters methyl 11-bromoundecanoate and methyl 11-methoxyundecanoate.

  报道了从一系列ω-溴羧酸Br(CH₂)ₙCOOH (n = 5到n = 11)的电解制备ω,ω′-二溴化物的首次成功实验。在相对较低的温度和电流密度条件下，获得了54%至71%的二溴化物产率。以11-溴十一酸的电解为例，讨论了实验条件的微小变化如何导致反应产物的显著变化。在50°时，主要产物是1,20-二溴二十烷，而在65°时，主要产物是酯类甲基-11-溴十一酸酯和甲基-11-甲氧基十一酸酯。
• Synthesis of Alkylene-Bridged Diphenyl-Oligoynes
  作者：Christian Klinger、Otto Vostrowsky、Andreas Hirsch

  DOI：10.1002/ejoc.200500851

  日期：2006.3

  Alkylene chains with up to 40 methylene groups were employed. The two terminal acetylene functions were introduced prior to the oligoyne elongation by twofold introduction of additional C2-acetylene or C4-butadiyne building blocks. The final step was the intramolecular acetylene coupling upon which very large macrocycles with up to 62 ring members containing segregated sp-, sp2- and sp3-segments were formed

  报道了用于制备由亚烷基桥稳定的低聚炔的一般合成路线。相应的大环包含具有多达八个共轭三键的低聚炔。共轭sp-寡炔棒的稳定是通过庞大的末端苯基端盖跨越亚烷基链来隔离单个炔棒并避免聚合来实现的。使用最多具有 40 个亚甲基的亚烷基链。通过双重引入额外的 C2-乙炔或 C4-丁二炔结构单元，在低聚炔延伸之前引入两个末端乙炔官能团。最后一步是分子内乙炔偶联，在此偶联上形成了具有多达 62 个环成员的非常大的大环，其中包含分离的 sp-、sp2-和 sp3-链段。(© Wiley-VCH Verlag GmbH & Co. KGaA,
• Intramolecular Reactions of Tethered Furan‐Based Bis( <i>p</i> ‐quinodimethanes)
  作者：Douglas A. Klumpp、Thomas M. Gilbert、Walter S. Trahanovsky

  DOI：10.1002/ejoc.201600995

  日期：2016.11

  generated in the gas phase by flash vacuum pyrolysis (FVP) of diester precursors. These furan-based bis(p-quinodimethanes) are shown to undergo reactions leading to macrocycles. The observed products strongly support a mechanism involving cyclic diradical intermediates. Formation of the furan-based p-quinodimethane and the corresponding cyclization chemistry was studied by high-level ab initio calculations

  通过二酯前体的快速真空热解 (FVP) 在气相中生成束缚的双-2,5-二亚甲基-2,5-二氢呋喃。这些基于呋喃的双（对醌二甲烷）显示出发生导致大环的反应。观察到的产物强烈支持涉及环状双自由基中间体的机制。通过高级 ab initio 计算研究了呋喃基对醌二甲烷的形成和相应的环化化学。理论研究揭示了熵驱动消除步骤在高温 FVP 化学中的重要性。

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