2-(2'-bromoethoxy)ethyl 2''-tetrahydropyranyl ether

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-(2'-bromoethoxy)ethyl 2''-tetrahydropyranyl ether
• 英文别名: 2-[2-(2-bromoethoxy)ethoxy]tetrahydro-2H-pyran；Bromo-PEG2-THP；2-[2-(2-bromoethoxy)ethoxy]oxane
• 化学式: C₉H₁₇BrO₃
• 分子量: 253.136
• InChiKey: UFIBMWVYNLIJBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-噻吩甲醇 、 2-(2'-bromoethoxy)ethyl 2''-tetrahydropyranyl ether 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 336.5h， 以78%的产率得到2-(2-(2-((2,5-dibromothiophen-3-yl)methoxy)ethoxy)ethoxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  β-取代的噻吩[2]轮烷

  摘要：

  迈向聚噻吩聚轮烷：已合成了β-取代的对噻吩[2]轮烷（见图）。还报道了合成的[2]轮烷的基本光学和电化学性质。

  DOI：

  10.1002/chem.200802120
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 2-(2-溴乙氧基)乙醇 反应 1.0h， 以71%的产率得到2-(2'-bromoethoxy)ethyl 2''-tetrahydropyranyl ether
  参考文献：
  名称：

  Novel benzene-bridged macrobi- and macrotricyclic polyethers

  摘要：

  Novel three-dimensional benzene-bridged macrobicyclic polyether 1 and macrotricyclic polyether 2 have been prepared. Macrobicyclic triply bridged cyclophane crown compound 1 was synthesized by a tripode-tripode coupling of 1,3,5-tris[7'-(tosyloxy)-2',5'-dioxa-1'-heptyl]benzene (19) with 1,3,5-tris(hydroxymethyl)benzene (5). Macrotricyclic quadruply bridged cyclophane crown ether 2 was obtained by a quadrupode-quadrupode coupling of 1,2,4,5-tetrakis(7'-tosyloxy-2,5'-dioxa-1'-heptyl)benzene (20) with 1,2,4,5-tetrakis(hydroxymethyl)benzene (6). These ligands could have suitable rigidity and cavity sizes for the coordination of metal cations. They appear to have selectivities for cesium over sodium and lead ions, and 2 shows a log K value of 3.50 for interaction with cesium ion in 80% CH3OH/20% water (v/v). Macrotricyclic polyether 2 containing benzene bridgeheads is a new type of ligand, and its structure was confirmed by an X-ray crystallographic study.

  DOI：

  10.1021/jo00079a013

文献信息

• Structure activity relationship of C-2 ether substituted 1,5-naphthyridine analogs of oxabicyclooctane-linked novel bacterial topoisomerase inhibitors as broad-spectrum antibacterial agents (Part-5)
  作者：Sheo B. Singh、David E. Kaelin、Peter T. Meinke、Jin Wu、Lynn Miesel、Christopher M. Tan、David B. Olsen、Armando Lagrutta、Hideyuki Fukuda、Ryuta Kishii、Masaya Takei、Tomoko Takeuchi、Hisashi Takano、Kohei Ohata、Haruaki Kurasaki、Akinori Nishimura、Takeshi Shibata、Yasumichi Fukuda

  DOI：10.1016/j.bmcl.2015.06.061

  日期：2015.9

  Oxabicyclooctane linked novel bacterial topoisomerase inhibitors (NBTIs) are new class of recently reported broad-spectrum antibacterial agents. They target bacterial DNA gyrase and topoisomerase IV and bind to a site different than quinolones. They show no cross-resistance to known antibiotics and provide opportunity to combat drug-resistant bacteria. A structure activity relationship of the C-2 substituted

  氧杂双环辛烷连接的新型细菌拓扑异构酶抑制剂（NBTI）是最近报道的一类新型广谱抗菌剂。它们靶向细菌DNA促旋酶和拓扑异构酶IV，并结合到不同于喹诺酮的位点。它们对已知的抗生素没有交叉耐药性，并提供了对抗耐药菌的机会。描述了与1，5-萘啶氧杂双环辛烷连接的NBTI的C-2取代的醚类似物的结构活性关系。已经总结出总共63种类似物的合成和抗菌活性，它们代表烷基，环烷基，氟代烷基，羟烷基，氨基烷基和羧基烷基醚。所有化合物均针对三种革兰氏阳性菌和革兰氏阴性菌以及hERG结合活性进行了测试。还测试了许多关键化合物的功能性hERG活性。在鼠菌血症模型中评价了六种化合物的功效。金黄色葡萄球菌感染。对于金黄色葡萄球菌活性，在C-2处观察到对醚取代（包括极性基团，例如氨基和羧基）的显着耐受性，但是对于粪肠球菌和革兰氏阴性菌株而言，情况并非如此。降低的c  log  D通常显示出降低的hERG活性和改善的体内功
• [EN] ETHYLENE GLYCOL ETHER OF BUPRENORPHINE<br/>[FR] ÉTHER DE L'ÉTHYLÈNEGLYCOL DE BUPRÉNORPHINE
  申请人：ORPHOMED INC

  公开号：WO2017074904A1

  公开（公告）日：2017-05-04

  A novel ethylene glycol ether of buprenorphine for oral administration and its the treatment of chronic pain.

  一种用于口服的布洛芬诺啡新型乙二醇醚及其治疗慢性疼痛的方法。
• ETHYLENE GLYCOL ETHER OF BUPRENORPHINE
  申请人：Orphomed, Inc.

  公开号：EP3368038A1

  公开（公告）日：2018-09-05
• [EN] OLIGOMERIC AMINO ACID DERIVATIVES USEFUL AS NITRIC OXIDE SYNTHASE INHIBITORS<br/>[FR] DERIVES OLIGOMERIQUES D'ACIDES AMINES UTILISES COMME INHIBITEURS DE L'OXYDE NITRIQUE SYNTHASE
  申请人：MONSANTO CO

  公开号：WO2001005748A1

  公开（公告）日：2001-01-25

  The current invention discloses novel oligomeric amidino aminocarboxylate derivatves useful as nitric oxide synthase inhibitors.
• Novel benzene-bridged macrobi- and macrotricyclic polyethers
  作者：Haoyun An、Jerald S. Bradshaw、Krzysztof E. Krakowiak、Bryon J. Tarbet、N. Kent Dalley、Xiaolan Kou、Chengyue Zhu、Reed M. Izatt

  DOI：10.1021/jo00079a013

  日期：1993.12

  Novel three-dimensional benzene-bridged macrobicyclic polyether 1 and macrotricyclic polyether 2 have been prepared. Macrobicyclic triply bridged cyclophane crown compound 1 was synthesized by a tripode-tripode coupling of 1,3,5-tris[7'-(tosyloxy)-2',5'-dioxa-1'-heptyl]benzene (19) with 1,3,5-tris(hydroxymethyl)benzene (5). Macrotricyclic quadruply bridged cyclophane crown ether 2 was obtained by a quadrupode-quadrupode coupling of 1,2,4,5-tetrakis(7'-tosyloxy-2,5'-dioxa-1'-heptyl)benzene (20) with 1,2,4,5-tetrakis(hydroxymethyl)benzene (6). These ligands could have suitable rigidity and cavity sizes for the coordination of metal cations. They appear to have selectivities for cesium over sodium and lead ions, and 2 shows a log K value of 3.50 for interaction with cesium ion in 80% CH3OH/20% water (v/v). Macrotricyclic polyether 2 containing benzene bridgeheads is a new type of ligand, and its structure was confirmed by an X-ray crystallographic study.