7-[(triphenylmethyl)oxy]heptanol | 82777-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 7-[(triphenylmethyl)oxy]heptanol
• 英文别名: 7-(triphenylmethoxy)heptanol；7-(trityloxy)heptan-1-ol；7-trityloxyheptan-1-ol；1-Heptanol, 7-(triphenylmethoxy)-
• CAS: 82777-71-7
• 化学式: C₂₆H₃₀O₂
• 分子量: 374.523
• InChiKey: WRYDZWJWQYDDMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-[(triphenylmethyl)oxy]heptanol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 、 三氟甲磺酸酐 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 aq. phosphate buffer 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 oxocan-2-one
  参考文献：
  名称：

  醇和醚在室温下直接酰胺化成酰胺：合成的“酰胺策略”

  摘要：

  最后一分钟的交易：据报道，醚和醇在酰胺的直接内酯化反应在室温下，在温和条件下进行（见方案）。这允许在合成序列中有效节省多达两个非生产性的顺序脱保护操作。描述了机理研究，并概述了利用该官能团的双重鲁棒性/后期选择性激活特性的新“酰胺策略”。

  DOI：

  10.1002/chem.201203906
• 作为产物：
  描述：

  1,7-庚二醇 、 三苯基氯甲烷 以 吡啶 、 二氯甲烷 为溶剂， 以57%的产率得到7-[(triphenylmethyl)oxy]heptanol
  参考文献：
  名称：

  拴系三糖的合成，以探讨糖-蛋白相互作用中糖间的柔性。

  摘要：

  三糖表位的两个晶体结构alpha-D-Galp（1-> 2）[alpha-D-Abep（1-> 3）alpha-D-Manp1-> OCH（3）1与抗体Fab和单链Fv片段已用于指导分子内束缚的设计，该束缚将三糖配体约束为接近结合态的构象。配体的预组织应克服对结合的熵罚并提供增强的亲和力。使用三个系链[O（CH（2））（n）（）O，n = 6、7和8]固定甘露糖和半乳糖残基的溶剂暴露C6原子。使用了两种合成方案。第一种使用带有被保护为三苯甲基醚6-8的系链的1-硫代半乳糖苷乙基。供体6-8中的任何一个在C6处含有甲磺酸盐的甘露吡喃糖苷5的糖基化得到二糖37-39。随后除去三苯甲基，允许在系链的ω-羟基上生成醇盐，以38％的收率置换磺酸盐。通过比较，当掺入ω-甲磺酰氧基系绳作为甘露糖苷9时，与半乳糖基供体10反应后的二糖产物52以61％的产率转化为大环4。通过硫代糖苷化学法引入3，6-二脱氧

  DOI：

  10.1021/jo9806097

文献信息

• Polymer-Supported Sulfinimidoyl Chlorides: A Convenient Reagent for Oxidation of Alcohols
  作者：Jun-ichi Matsuo、Asahi Kawana、Hiroyuki Yamanaka、Hiroaki Kamiyama

  DOI：10.1246/bcsj.76.1433

  日期：2003.7

  polymer-supported sulfinimidoyl chlorides, i.e., 4-(N-tert-butylchlorosulfinimidoyl)phenoxymethylpolystyrene (3) and 4-(N-tert-butylchlorosulfinimidoyl)polystyrene (10), were prepared from chloromethylpolystyrene and polystyrene, respectively. Stoichiometric or catalytic oxidation of various primary and secondary alcohols using these polymer-supported sulfinimidoyl chlorides proceeded smoothly, and the

  分别由氯甲基聚苯乙烯和聚苯乙烯制备了两种聚合物负载的亚磺酰亚胺酰氯，即 4-(N-叔丁基氯亚磺酰亚胺酰基)苯氧基甲基聚苯乙烯 (3) 和 4-(N-叔丁基氯亚磺酰亚胺酰基) 聚苯乙烯 (10)。使用这些聚合物负载的亚磺酰亚胺酰氯对各种伯醇和仲醇进行化学计量或催化氧化反应顺利进行，相应的醛和酮可以通过简单的后处理程序以良好到高的产率方便地制备。聚合物负载的氧化剂10在化学计量氧化后通过用N-氯代琥珀酰亚胺(NCS)氯化用过的聚合物11而重复循环。
• Polymer-supported Sulfinimidoyl Chloride as a Useful Reagent for Oxidation of Various Alcohols to the Corresponding Carbonyl Compounds
  作者：Jun-ichi Matsuo、Asahi Kawana、Khanitha Pudhom、Teruaki Mukaiyama

  DOI：10.1246/cl.2002.250

  日期：2002.2

  Polymer-supported sulfinimidoyl chloride was prepared in four steps from chloromethyl polystyrene resin. Stoichiometric and catalytic oxidations of various alcohols to the corresponding carbonyl compounds were carried out cleanly by using the prepared polymer-bound oxidant.

  以氯甲基聚苯乙烯树脂为原料，分四步制备聚合物负载的亚磺酰亚胺酰氯。通过使用制备的聚合物结合氧化剂，将各种醇化学计量和催化氧化成相应的羰基化合物。
• <i>N</i>-Substituted Thymine Derivatives as Mitochondrial Thymidine Kinase (TK-2) Inhibitors
  作者：Ana-Isabel Hernández、Olga Familiar、Ana Negri、Fátima Rodríguez-Barrios、Federico Gago、Anna Karlsson、María-José Camarasa、Jan Balzarini、María-Jesús Pérez-Pérez

  DOI：10.1021/jm0610550

  日期：2006.12.1

  Novel N-1-substituted thymine derivatives related to 1-[(Z)-4-(triphenylmethoxy)-2-butenyl]thymine have been synthesized and evaluated against thymidine kinase-2 (TK-2) and related nucleoside kinases [i.e., Drosophila melanogaster deoxynucleoside kinase (Dm-dNK) and herpes simplex virus type 1 thymidine kinase (HSV-1 TK)]. The thymine base has been tethered to a distal triphenylmethoxy moiety through a polymethylene chain (n = 3-8) or through a (2-ethoxy)ethyl spacer. Moreover, substitutions at position 4 of one of the phenyl rings of the triphenylmethoxy moiety have been performed. Compounds with a hexamethylene spacer (18, 26b, 31) displayed the highest inhibitory values against TK-2 (IC50 = 0.3-0.5 mu M). Compound 26b competitively inhibited TK-2 with respect to thymidine and uncompetitively with respect to ATP. A rationale for the biological data was provided by docking some representative inhibitors into a homology-based model of human TK-2. Moreover, two of the most potent TK-2 inhibitors (18 and 26b) that also inhibit HSV-1 TK were able to reverse the cytostatic activity of 1-(beta-D-arabinofuranosyl)thymine (Ara-T) and ganciclovir in HSV-1 TK-expressing OST-TK-/HSV-1 TK+ cell cultures.
• New Antibacterial Agents Derived from the DNA Gyrase Inhibitor Cyclothialidine
  作者：Peter Angehrn、Stefan Buchmann、Christoph Funk、Erwin Goetschi、Hans Gmuender、Paul Hebeisen、Dirk Kostrewa、Helmut Link、Thomas Luebbers、Raffaello Masciadri、Joergen Nielsen、Peter Reindl、Fabienne Ricklin、Anne Schmitt-Hoffmann、Frank-Peter Theil

  DOI：10.1021/jm0310232

  日期：2004.3.1

  Cyclothialidine (1, Ro 09-1437) is a potent DNA gyrase inhibitor that was isolated from Streptomyces filipinensis NR0484 and is a member of a new family of natural products. It acts by competitively inhibiting the ATPase activity exerted by the B subunit of DNA gyrase but barely exhibits any growth inhibitory activity against intact bacterial cells, presumably due to insufficient permeation of the cytoplasmic membrane. To explore the antibacterial potential of 1, we developed a flexible synthetic route allowing for the systematic modification of its structure. From a first set of analogues, structure-activity relationships (SAR) were established for different substitution patterns, and the 14-hydroxylated, bicyclic core (X) of 1 seemed to be the structural prerequisite for DNA gyrase inhibitory activity. The variation of the lactone ring size, however, revealed that activity can be found among 11- to 16-membered lactones, and even seco-analogues were shown to maintain some enzyme inhibitory properties, thereby reducing the minimal structural requirements to a rather simple, hydroxylated benzyl sulfide (XI). On the basis of these "minimal structures" a modification program afforded a number of inhibitors that showed in vitro activity against Gram-positive bacteria. The best activities were displayed by 14-membered lactones, and representatives of this subclass exhibit excellent and broad in vitro antibacterial activity against Gram-positive pathogens, including Staphylococcus aureus, Streptococcus pyogenes, and Enterococcus faecalis, and overcome resistance against clinically used drugs. By improving the pharmacokinetic properties of the most active compounds (94, 97), in particular by lowering their lipophilic properties, we were able to identify congeners of cyclothialidine (1) that showed efficacy in vivo.
• Synthesis of Tethered Trisaccharides To Probe Inter-Saccharide Flexibility in Carbohydrate−Protein Interactions
  作者：Ramon Alibés、David R. Bundle

  DOI：10.1021/jo9806097

  日期：1998.9.1

  Two crystal structures of the trisaccharide epitope alpha-D-Galp(1-->2)[alpha-D-Abep(1-->3)alpha-D-Manp1-->OCH(3) 1 bound to antibody Fab and single-chain Fv fragments have been used to guide the design of an intramolecular tether that constrains the trisaccharide ligand to conformations close to those of the bound state. Preorganization of the ligand should overcome entropic penalties to binding and

  三糖表位的两个晶体结构alpha-D-Galp（1-> 2）[alpha-D-Abep（1-> 3）alpha-D-Manp1-> OCH（3）1与抗体Fab和单链Fv片段已用于指导分子内束缚的设计，该束缚将三糖配体约束为接近结合态的构象。配体的预组织应克服对结合的熵罚并提供增强的亲和力。使用三个系链[O（CH（2））（n）（）O，n = 6、7和8]固定甘露糖和半乳糖残基的溶剂暴露C6原子。使用了两种合成方案。第一种使用带有被保护为三苯甲基醚6-8的系链的1-硫代半乳糖苷乙基。供体6-8中的任何一个在C6处含有甲磺酸盐的甘露吡喃糖苷5的糖基化得到二糖37-39。随后除去三苯甲基，允许在系链的ω-羟基上生成醇盐，以38％的收率置换磺酸盐。通过比较，当掺入ω-甲磺酰氧基系绳作为甘露糖苷9时，与半乳糖基供体10反应后的二糖产物52以61％的产率转化为大环4。通过硫代糖苷化学法引入3，6-二脱氧