(4-acetoxybutyl)triphenylphosphonium bromide | 6191-70-4

• 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: (4-acetoxybutyl)triphenylphosphonium bromide
• 英文别名: 4-Acetyloxybutyl(triphenyl)phosphanium;bromide
• CAS: 6191-70-4
• 化学式: Br*C₂₄H₂₆O₂P
• 分子量: 457.347
• InChiKey: WVBBBQKPXICVPN-UHFFFAOYSA-M

物化性质

• 熔点：
  >111°C (dec.)
• 溶解度：
  可溶于乙腈（少许）、DMSO（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-acetoxybutyl)triphenylphosphonium bromide 在 palladium on activated charcoal 二环己烷并-18-冠醚-6 、 三(三氟乙酸)碘 、 potassium tert-butylate 、 氢气 、 铜 、 三乙胺 、 sodium bromide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 3'-(5-acetoxypentyl)-3,5-diiodo-N-(trifluoroacetyl)-O-methyl-L-thyronine methyl ester
  参考文献：
  名称：

  Thyroid hormone analogs. Synthesis of 3'-substituted 3,5-diiodo-L-thyronines and quantitative structure-activity studies of in vitro and in vivo thyromimetic activities in rat liver and heart

  摘要：

  Twenty-nine novel 3'-substituted derivatives of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3) have been synthesized by using established methods and by a new route involving manipulation of a 3'-formyl intermediate. In vitro hormone receptor binding (to intact nuclei) and in vivo thyromimetic activity (induction of mitochondrial 3-phosphoglycerate oxidoreductase, GPDH) were measured in rat liver and heart for these new analogues and for the 18 previously reported 3'-substituted 3,5-diiodo-L-thyronines. Analysis of the binding data using theoretical conformational and quantitative structure-affinity methods implies that the 3'-substituent recognition site on the thyroid hormone receptor is hydrophobic and limited in depth to the length of the natural iodo substituent, but has sufficient width to accommodate a phenyl or cyclohexyl group. Receptor binding is reduced by approximately 10-fold in 3'-acyl derivatives which form strong intramolecular acceptor hydrogen bonds with the adjacent 4'-hydroxyl. The compounds studied showed no differences in their relative affinities for heart and liver nuclei, suggesting that receptors in these tissues are similar. However, the relationships between thyromimetic activity (induction of GPDH) and nuclear binding showed some tissue differences. A high correlation between activity and binding is observed for full agonists in the heart, but an equally significant correlation for the liver data is only seen when 3'-substituent bulk (molar refractivity) is included in the analysis. These results suggest the possibility that differential tissue penetration or access to receptors may occur in vivo.

  DOI：

  10.1021/jm00396a008
• 作为产物：
  描述：

  三苯基膦 以 水 、 丙酮 、 甲苯 为溶剂， 反应 30.0h， 生成 (4-acetoxybutyl)triphenylphosphonium bromide
  参考文献：
  名称：

  酰氧基烷基亚叉基膦酸酯-II：ω-酰氧基正丁基对苯甲基萘基膦酸酯。Nouvelle Voie d'accèsaux dihydro-3,4 2h-pyrannes

  摘要：

  ω-酰氧基正丁基亚氨基三苯基苯基膦通过在t - BuOH中的分子间缩合生成α-酰基正丁基亚甲基三苯基苯基膦，并通过在甲苯中的分子内缩合生成3,4-二氢-（2H）-吡喃。作为α-酰基氧杂膦的互变异构形式的α-酰基正丁叉基膦烷不导致环丁基酮而是二氢吡喃。

  DOI：

  10.1016/s0040-4020(01)92356-7

文献信息

• One-Pot Regio- and Stereoselective Cyclization of 1,2,<i>n</i>-Triols
  作者：Tao Zheng、Radha S. Narayan、Jennifer M. Schomaker、Babak Borhan

  DOI：10.1021/ja043002i

  日期：2005.5.1

  A simple and efficient process to cyclize triols containing a 1,2-diol functionality with a pendant hydroxyl group is presented. The one-pot procedure converts the 1,2-diol into an ortho ester in situ, which upon treatment with a Lewis acid generates a cyclic acetoxonium intermediate. This intermediate is subsequently trapped by the pendant hydroxyl group to generate a cyclic ether. The stereochemistry

  提出了一种简单有效的方法来环化含有 1,2-二醇官能团和侧羟基的三醇。一锅法将 1,2-二醇原位转化为原酸酯，在用路易斯酸处理后生成环状丙酮鎓中间体。该中间体随后被侧羟基捕获以生成环醚。1,2-二醇的立体化学完全保真（在环化位点反转）转移到产物中，反应以高区域选择性进行。该过程类似于路易斯酸催化的带有羟基的环氧化物分子内开环，产生具有区域和立体化学控制的各种尺寸的环醚。
• COMPOSITIONS AND METHODS FOR CHEMICAL CLEAVAGE AND DEPROTECTION OF SURFACE-BOUND OLIGONUCLEOTIDES
  申请人：Illumina, Inc.

  公开号：US20190352327A1

  公开（公告）日：2019-11-21

  Embodiments of the present disclosure relate to methods of preparation of templates for polynucleotide sequencing. In particular, the disclosure relates to linearization of clustered polynucleotides in preparation for sequencing by cleavage of one or more first strands of double-stranded polynucleotides immobilized on a solid support by a transition metal complex, for example, a palladium complex or a nickel complex. Further disclosure relate to linearization of clustered polynucleotides by cleaving one or more second strands of double double-stranded polynucleotides immobilized on a solid support comprising azobenzene linker by Na 2 S 2 O 4 . Nucleotides and oligonucleotides comprising a 3′ phosphate moiety blocking group, and methods of removing the same using a fluoride reagent are also disclosed.

  本公开的实施例涉及用于多核苷酸测序模板制备的方法。具体而言，本公开涉及通过过渡金属络合物（例如钯络合物或镍络合物）裂解固定在固体支持物上的双链多核苷酸的一条或多条第一链，以便为测序做准备。进一步公开涉及通过Na2S2O4裂解固定在含有偶氮苯联结剂的固体支持物上的双链多核苷酸的一条或多条第二链来线性化团簇化的多核苷酸。还公开了含有3'磷酸酯基团阻断基团的核苷酸和寡核苷酸，以及使用氟化试剂去除这些基团的方法。
• Method for pairwise sequencing of target polynucleotides
  申请人：Illumina Cambridge Limited

  公开号：US09267173B2

  公开（公告）日：2016-02-23

  The invention relates to methods for pairwise sequencing of a double-stranded polynucleotide template, which methods result in the sequential determination of nucleotide sequences in two distinct and separate regions of the polynucleotide template. Using the methods of the invention it is possible to obtain two linked or paired reads of sequence information from each double-stranded template on a clustered array, rather than just a single sequencing read from one strand of the template.

  该发明涉及一种双链多核苷酸模板的成对测序方法，该方法导致在多核苷酸模板的两个不同和独立区域中顺序确定核苷酸序列。利用该发明的方法，可以从聚集阵列上的每个双链模板获得两个连接或成对的序列信息读取，而不仅仅是从模板的一条链上获得单个测序读取。
• Preparation of Templates for Nucleic Acid Sequencing
  申请人：Illumina Cambridge Limited

  公开号：US20150343410A1

  公开（公告）日：2015-12-03

  The invention relates to methods of generating templates for a nucleic acid sequencing reaction which comprise: providing at least one double-stranded nucleic acid molecule, wherein both strands of the double-stranded nucleic acid molecule are attached to a solid support at the 5′ end, cleaving one or both strands of the double-stranded nucleic acid molecule, and subjecting the cleaved strand(s) to denaturing conditions to remove the portion of the cleaved strand(s) not attached to the solid support, thereby generating a partially or substantially single-stranded template for a nucleic acid sequencing reaction.

  这项发明涉及用于生成核酸测序反应模板的方法，包括：提供至少一种双链核酸分子，其中双链核酸分子的两条链均连接在固体支持物上的5'端，裂解双链核酸分子的一条或两条链，并将裂解的链置于变性条件下，以去除未连接到固体支持物的裂解链部分，从而生成用于核酸测序反应的部分或基本上单链模板。
• Synthesis of hydroxy-α-sanshool
  作者：Jianjun Zhou、Yan Xiao、Taiping Chen、Jiyu Gao、Wencai Huang、Zicheng Li

  DOI：10.1177/1747519820974323

  日期：2021.3

  Hydroxy-α-sanshool was synthesized in a 13% overall yield through eight steps, which included two Wittig reactions that were used to form the carbon skeleton with ethyl 2-oxoacetate and 2 E,4 E-hexadienal being reacted with the appropriate ylides. Impurities in the processes could easily be separated. Ethyl 6-hydroxy-2Z-hexenoate was converted to its E-isomer with catalysis by I₂ and 2E,6Z,8E,10E-dodecatetraenoic acid was crystallized from a solution in 1% ethyl acetate in n-hexane.

  氢氧-α-山椒醇通过八个步骤合成，总产率为13％，其中包括两个威廉反应，用乙酸乙酯和2E,4E-己二烯醛与适当的叶烯反应形成碳骨架。过程中的杂质可以很容易地分离。乙酸乙酯6-羟基-2Z-己烯酸酯通过I2催化转化为其E异构体，2E,6Z,8E,10E-十二碳四烯酸在1％乙酸乙酯和正己烷溶液中结晶。