(8-hydroxyoctyl)triphenylphosphonium bromide | 65734-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (8-hydroxyoctyl)triphenylphosphonium bromide
• 英文别名: Phosphonium, (8-hydroxyoctyl)triphenyl-, bromide；8-hydroxyoctyl(triphenyl)phosphanium;bromide
• CAS: 65734-62-5
• 化学式: Br*C₂₆H₃₂OP
• 分子量: 471.417
• InChiKey: IGIXSZMDWZOLMV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8-hydroxyoctyl)triphenylphosphonium bromide 在 platinum(IV) oxide N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 氢气 、 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 21.34h， 生成 Methyl 4-[9-(2,4-dichlorophenyl)nonylsulfanyl]-3-oxobutanoate
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w
• 作为产物：
  描述：

  1,8-辛二醇 在 氢溴酸 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 48.0h， 生成 (8-hydroxyoctyl)triphenylphosphonium bromide
  参考文献：
  名称：

  Recoverable solvent-free small molecular supramolecular pseudoeutectic adhesives with a wide temperature range

  摘要：

  据报道，一种以羟基鏻盐为单体的创新型无溶剂假共晶粘合剂在宽广的温度范围内具有出色的可回收性和强大的粘合力。

  DOI：

  10.1039/d3gc01253k

文献信息

• [EN] COMPOUNDS AND COMPOSITIONS FOR INTRACELLULAR DELIVERY OF THERAPEUTIC AGENTS<br/>[FR] COMPOSÉS ET COMPOSITIONS D'ADMINISTRATION INTRACELLULAIRE D'AGENTS THÉRAPEUTIQUES
  申请人：MODERNATX INC

  公开号：WO2018170306A1

  公开（公告）日：2018-09-20

  The disclosure features novel lipids and compositions involving the same. Nanoparticle compositions include a novel lipid as well as additional lipids such as phospholipids, structural lipids, and PEG lipids. Nanoparticle compositions further including therapeutic and/or prophylactics such as RNA are useful in the delivery of therapeutic and/or prophylactics to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.

  该披露涉及新型脂质和相关组合物。纳米粒子组合物包括一种新型脂质以及额外的脂质，如磷脂、结构脂质和PEG脂质。纳米粒子组合物还包括治疗和/或预防措施，如RNA，在将治疗和/或预防措施传递给哺乳动物细胞或器官方面非常有用，例如，调节多肽、蛋白质或基因表达。
• Phosphonioalkylthiosulfate zwitterions—new masked thiol ligands for the formation of cationic functionalised gold nanoparticles
  作者：Yon Ju-Nam、Neil Bricklebank、David W. Allen、Philip H. E. Gardiner、Mark E. Light、Michael B. Hursthouse

  DOI：10.1039/b610480k

  日期：——

  We report the synthesis and structural characterisation of a new family of stable phosphonioalkylthiosulfate zwitterions, R3P+(CH2)nS2O3− (R = Ph or Bu, n = 3,4,6, 8 or 10) which behave as cationic masked thiolate ligands with applications in the functionalisation of gold nanoparticles, having potential as new diagnostic biorecognition systems. The ligands were prepared by treatment of ω-bromoalkylphosphonium salts with sodium thiosulfate. The crystal and molecular structures of the zwitterions (R = Ph, n = 3) and (R = Bu, n = 3) were determined. A series of phosphonioalkanethiolate-capped gold nanoparticles dispersed in water was prepared by borohydride reduction of potassium tetrachloroaurate in the presence of the zwitterions in a dichloromethane–water system. UV-visible spectroscopy and scanning transmission electron-microscopy indicated that capped nanoparticles of ca. 5 nm diameter were present.

  我们报道了一类新型稳定的膦氧烷基硫代硫酸酯两性离子R3P+(CH2)nS2O3â的合成与结构表征，其中R为苯基或丁基，n为3、4、6、8或10，这些化合物作为阳离子型掩蔽硫醇盐配体，用于功能化金纳米粒子，具有作为新型生物诊断识别系统的潜力。这些配体是通过用硫代硫酸钠处理Ï-溴代烷基磷盐来制备的。我们对(R=苯基，n=3)和(R=丁基，n=3)两性离子的晶体和分子结构进行了测定。通过在二氯甲烷-水体系中，在两性离子存在下用硼氢化钠还原四氯金酸钾，制备了一系列分散于水的膦氧烷基硫醇盐包覆的金纳米粒子。紫外-可见光谱和扫描透射电子显微镜表明存在直径约为5纳米的包覆纳米粒子。
• Stereochemical observations on the Wittig reaction of oxido phosphonium ylides with aldehydes
  作者：Bruce E. Maryanoff、Allen B. Reitz、Barbara A. Duhl-Emswiler

  DOI：10.1016/s0040-4039(00)81959-0

  日期：1983.1

  The reaction of aldehydes with oxido ylides shows a dramatic dependence of alkene stereochemistry on the distance between oxygen and phosphorus atomsl; ylides with proximal 0 and P atoms favor production of alkenes. The high stereoselectivity with γ-oxido ylides is not mainly attributable to intramolecular proton-exchange in a Wittig intermediate.

  醛与氧化物的反应表明，烯烃立体化学对氧原子与磷原子之间的距离有显着的依赖性。具有近端0和P原子的芳基有利于烯烃的生产。γ-氧化酰基的高立体选择性主要不是归因于Wittig中间体中的分子内质子交换。
• An easy access to symmetrical Z-olefins from phosphorus ylides
  作者：S. Poulain、N. Noiret、H. Patin

  DOI：10.1016/0040-4039(96)01737-6

  日期：1996.10

  Symmetrical Z-olefins are obtained in good to quantitative yields from phosphonium salts via an autoxidation process, in salt-free conditions.

  在无盐条件下，通过自氧化过程，可以从phospho盐以良好的定量收率获得对称的Z-烯烃。
• Synthesis of insect sex pheromones and their homologues. 2. A convenient method for synthesizing (Z)-alkenols and their acetates.
  作者：Michio HORIIKE、Masaru TANOUCHI、Chisato HIRANO

  DOI：10.1271/bbb1961.44.257

  日期：——

  (Z)-Alkenols and Their acetates have been synthesized by the Wittig reaction of (ω-hydroxyalkyl)triphenylphosphonium salts with alkanals by a convenient procedure. The geometrical purity of the products was evaluated to be no less than 95% of the (Z)-configu-ration by means of GLC with a glass capillary column coated with CHDMS.

  通过一种简便的方法，利用Wittig反应将（ω-羟基烷基）三苯基膦盐与烷基醛反应，合成了（Z）-烯醇及其乙酸酯。通过涂有CHDMS的玻璃毛细管柱进行GC分析，评估产物的几何纯度不小于95%的（Z）构型。