1-溴-10-(甲氧基甲氧基)癸烷 | 252316-67-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-溴-10-(甲氧基甲氧基)癸烷
• 英文名称: 1-bromo-10-(methoxymethoxy)decane
• 英文别名: 1-Bromo-10-(methoxymethoxy)decane
• CAS: 252316-67-9
• 化学式: C₁₂H₂₅BrO₂
• 分子量: 281.233
• InChiKey: ULRPQGFCFHHKNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-溴-10-(甲氧基甲氧基)癸烷 在 2,2'-联吡啶 、 三氟甲磺酸三甲基硅酯 、 水 作用下， 以 二氯甲烷 、 乙醚 为溶剂， 反应 7.5h， 以88%的产率得到10-溴-1-癸醇
  参考文献：
  名称：

  The reaction of acetal-type protective groups in combination with TMSOTf and 2,2′-bipyridyl; mild and chemoselective deprotection and direct conversion to other protective groups

  摘要：

  A mild and chemoselective deprotection method of various acetal-type protective groups, such as MOM, MEM, BOM, and SEM ethers, has been developed. The combination of TMSOTf and 2,2'-bipyridyl was very effective for the deprotection, and the reaction proceeded via the formation of pyridinium intermediates, which were hydrolyzed to the corresponding alcohols in good to high yields. The features of this method are mild (almost neutral) reaction conditions and the tolerability of acid-sensitive functional groups. This method is also applicable for the direct conversion of MOM ether to BOM or SEM ether using the appropriate alcohols instead of H2O. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.048
• 作为产物：
  描述：

  10-溴癸醛 在 sodium tetrahydroborate 、 水 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-溴-10-(甲氧基甲氧基)癸烷
  参考文献：
  名称：

  New prodrugs of Adefovir and Cidofovir

  摘要：

  New Adefovir (PMEA) prodrugs with a pro-moiety consisting of decyl or decyloxyethyl chain bearing hydroxyl function(s), hexaethyleneglycol or a (5-methyl-2-oxo-1,3-dioxolen-4-yl) methyl unit were prepared starting from the tetrabutylammonium salt of the phosphonate drug and an appropriate alkyl bromide or tosylate. Analogously, two esters of Cidofovir [(S)-HPMPC] bearing a hexaethyleneglycol moiety were prepared. The activity of the prodrugs was evaluated in vitro against different virus families. A loss in the antiviral activities of the hydroxylated decyl or decyloxyethyl esters and hexaethyleneglycol esters of PMEA against human immunodeficiency virus (HIV) and herpesviruses [ including herpes simplex virus (HSV), varicella-zoster virus (VZV), and human cytomegalovirus (CMV)] occurred in comparison with the parent compound. On the other hand, the (5-methyl-2-oxo-1,3-dioxolen-4-yl) methyl ester of PMEA showed significant activities against HIV and herpesviruses. (S)-HPMPC prodrugs exhibited anti-cytomegalovirus activities in the same range as the parent drug, whereas the anti-HSV and anti-VZV activities were one-to seven-fold lower than that of Cidofovir. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.016

文献信息

• A Macrocyclic Phenanthroline–Copper Complex with Less Steric Hindrance: Synthesis, Structure, and Application to the Synthesis of a [2]Rotaxane
  作者：Shinichi Saito、Takanori Ohkubo、Yukari Yamazaki、Tatsuyuki Yokoyama、Yuichiro Mutoh、Ryu Yamasaki、Takeshi Kasama

  DOI：10.1246/bcsj.20150168

  日期：2015.9.15

  We synthesized a macrocyclic 2,9-dialkyl-1,10-phenanthroline–Cu complex (9) from 1,10-phenanthroline. Compound 9 existed as a dinuclear complex in solid state. In solution, however, the compound existed as a mononuclear complex. Compound 9 mediated the Glaser reaction of an alkyne with a bulky blocking group and the formation of a [2]rotaxane was observed. The reactivity of the 2,9-dialkyl-1,10-phenanthroline–Cu complex (9) was lower than that of a diaryl analogue.

  我们从 1,10-菲罗啉合成了一种大环 2,9-二烷基-1,10-菲罗啉-铜配合物（9）。化合物 9 在固态下以双核络合物的形式存在。但在溶液中，该化合物以单核络合物的形式存在。化合物 9 介导了炔烃与大块封端基团的格拉塞反应，并观察到 [2]rotaxane 的形成。2,9-二烷基-1,10-菲罗啉-铜复合物（9）的反应活性低于二芳基类似物。
• Synthesis of [16,16,16-2H3] 11-hexadecynoic acid and [15,15,16,16,16-2H5] (Z,Z)-11,13-hexadecadienoic acid and their use as tracers in a key step of the sex pheromone biosynthesis of the processionary moth.
  作者：Mireia Barrot、Gemma Fabriás、Francisco Camps

  DOI：10.1016/s0040-4020(01)85545-9

  日期：1994.1

  The synthesis of deuterium labeled 11-hexadecynoic acid and (Z,Z)-11,13-hexadecadienoic acid and their use to investigate the biosynthetic pathway of the processionary moth sex pheromone is reported. In [16,16,16-H-2(3)] 11-hexadecynoic acid, deuterium atoms were introduced by reaction of iodoalkyne 6b with (CD3)(2)CuLi. Alkylation of terminal diyne 14b with CD3CD2I followed by stereoselective reduction of the corresponding diyne to the corresponding (Z,Z) diene afforded [15,15,16,16,16-H-2(5)] (Z,Z)-11,13-hexadecadienoic acid. GLC-MS analyses of extracts from pheromone glands incubated with these tracers revealed that the acetylenic acid, but not the dienoic acid, is a precursor of the pheromone enyne system.
• The reaction of acetal-type protective groups in combination with TMSOTf and 2,2′-bipyridyl; mild and chemoselective deprotection and direct conversion to other protective groups
  作者：Hiromichi Fujioka、Yutaka Minamitsuji、Ozora Kubo、Kento Senami、Tomohiro Maegawa

  DOI：10.1016/j.tet.2011.02.048

  日期：2011.4

  A mild and chemoselective deprotection method of various acetal-type protective groups, such as MOM, MEM, BOM, and SEM ethers, has been developed. The combination of TMSOTf and 2,2'-bipyridyl was very effective for the deprotection, and the reaction proceeded via the formation of pyridinium intermediates, which were hydrolyzed to the corresponding alcohols in good to high yields. The features of this method are mild (almost neutral) reaction conditions and the tolerability of acid-sensitive functional groups. This method is also applicable for the direct conversion of MOM ether to BOM or SEM ether using the appropriate alcohols instead of H2O. (C) 2011 Elsevier Ltd. All rights reserved.
• New prodrugs of Adefovir and Cidofovir
  作者：Tomáš Tichý、Graciela Andrei、Martin Dračínský、Antonín Holý、Jan Balzarini、Robert Snoeck、Marcela Krečmerová

  DOI：10.1016/j.bmc.2011.04.016

  日期：2011.6

  New Adefovir (PMEA) prodrugs with a pro-moiety consisting of decyl or decyloxyethyl chain bearing hydroxyl function(s), hexaethyleneglycol or a (5-methyl-2-oxo-1,3-dioxolen-4-yl) methyl unit were prepared starting from the tetrabutylammonium salt of the phosphonate drug and an appropriate alkyl bromide or tosylate. Analogously, two esters of Cidofovir [(S)-HPMPC] bearing a hexaethyleneglycol moiety were prepared. The activity of the prodrugs was evaluated in vitro against different virus families. A loss in the antiviral activities of the hydroxylated decyl or decyloxyethyl esters and hexaethyleneglycol esters of PMEA against human immunodeficiency virus (HIV) and herpesviruses [ including herpes simplex virus (HSV), varicella-zoster virus (VZV), and human cytomegalovirus (CMV)] occurred in comparison with the parent compound. On the other hand, the (5-methyl-2-oxo-1,3-dioxolen-4-yl) methyl ester of PMEA showed significant activities against HIV and herpesviruses. (S)-HPMPC prodrugs exhibited anti-cytomegalovirus activities in the same range as the parent drug, whereas the anti-HSV and anti-VZV activities were one-to seven-fold lower than that of Cidofovir. (C) 2011 Elsevier Ltd. All rights reserved.