3,6,9,12,15,18-hexaoxaeicosan-1-ol | 4403-58-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6,9,12,15,18-hexaoxaeicosan-1-ol
• 英文别名: hexaethyleneglycol monoethyl ether；2-[2-(2-{2-[2-(2-ethoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethanol；O-Aethyl-hexaaethylenglykol；2-(2-(2-(2-(2-(2-Ethoxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethanol；2-[2-[2-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethanol
• CAS: 4403-58-1
• 化学式: C₁₄H₃₀O₇
• 分子量: 310.388
• InChiKey: UKXKPKBTMYNOFS-UHFFFAOYSA-N

物化性质

• 沸点：
  390.1±37.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)
• 保留指数：
  2118

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  21
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,6,9,12,15,18-hexaoxaeicosan-1-ol 在 四丁基氢氧化铵 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 1-(((5S)-2-((3,6,9,12,15,18-hexaoxaicosyl)oxy)-2-oxido-1,4,2-dioxaphosphinan-5-yl)methyl)-4-aminopyrimidin-2(1H)-one
  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
• 作为产物：
  描述：

  六甘醇 在 4-甲基苯磺酸吡啶 、 sodium hydride 、 potassium iodide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， 反应 102.25h， 生成 3,6,9,12,15,18-hexaoxaeicosan-1-ol
  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

• Formation of Macrocyclic Ethers by Free Radical Cyclization:  Effects of Chain Length, Substituents, and Solvents
  作者：Annie Philippon、Marie Degueil-Castaing、Athelstan L. J. Beckwith、Bernard Maillard

  DOI：10.1021/jo980259o

  日期：1998.10.1

  Free radical reduction by tributylstannane of omega-iodopolyoxaalkyl acrylates derived from tri-, tetra-, penta-, hexa-, and heptaethylene glycols gives mixtures of uncyclized reduction products and macrocyclic ethers formed by endo cyclization. The rate constants for cyclization of the intermediate radicals at 80 degrees C in benzene were determined under carefully defined conditions to be 15 x 10(4)

  通过三丁基锡烷自由基还原衍生自三，四，五，五，六和七乙二醇的ω-碘多聚氧杂烷基丙烯酸酯，得到未环化还原产物和通过内环化形成的大环醚的混合物。在精心定义的条件下，确定80℃下苯中的中间体自由基环化的速率常数为15 x 10（4），13 x 10（4），5.1 x 10（4），10 x 10（4）和3.6 x 10（4）s（-）（1），分别用于形成12、15、18、21和24元环。这些值表明，与先前报道的烯基物质的环化相比，链中氧原子的存在使速率增加了10-30倍。苯在80摄氏度时的速率常数和甲基丙烯酸酯，巴豆酸酯，已经确定了8-碘-3,6-二氧杂辛醇的肉桂酸酯，马来酸酯和富马酸酯。在极性不同的溶剂中丙烯酸8-碘-3,6-二氧杂辛酯的还原表明环化速率具有相对较低的溶剂依赖性。
• Method for Chlorinating Alcohols
  申请人：Rohde Thorsten

  公开号：US20080228016A1

  公开（公告）日：2008-09-18

  A process for preparing organic chlorides in which the chlorine atom is bonded to a CH 2 group by reacting the corresponding alcohols with thionyl chloride in the presence of a triaylphosphine oxide at a temperature of from 20 to 200° C. and a pressure of from 0.01 to 10 MPa abs, which comprises using the triarylphosphine oxide in a molar ratio to the amount of OH groups to be chlorinated of from 0.0001 to 0.5.

  一种制备有机氯化物的方法，其中氯原子与一个CH2基团结合，通过在20至200°C温度和0.01至10兆帕绝对压力下，在三芳基膦氧化物存在下，将相应的醇与亚砜氯反应。该方法包括使用三芳基膦氧化物，其与待氯化的OH基团的摩尔比为0.0001至0.5。
• Synthesis of penta-p-phenylenes with oligo(ethylene glycol) side chains
  作者：J. Manuel López-Romero、Rodrigo Rico、Rocío Martínez-Mallorquín、Jesús Hierrezuelo、Elena Guillén、Chengzhi Cai、J. Carlos Otero、Isabel López-Tocón

  DOI：10.1016/j.tetlet.2007.06.167

  日期：2007.8

  We report an efficient synthesis of a series of penta-p-phenylene derivatives with four side chains of various lengths, including deca(ethylene glycol) groups. The key feature of the synthesis is that the side chains are efficiently introduced in the last step, facilitating optimization of the side chains for different applications. Raman spectroscopy study indicates a similarly high rigidity for all

  我们报告了一系列具有四个不同长度的侧链的五对苯撑衍生物的有效合成，包括十个（乙二醇）基团。合成的关键特征是在最后一步中有效地引入了侧链，从而有助于针对不同应用优化侧链。拉曼光谱研究表明，所有这些化合物都具有相似的高刚性，即使是具有长寡聚（乙二醇）侧链的化合物。十（乙二醇）取代的五对苯撑衍生物是用于构建生物应用的纳米三脚架形吸附物的多功能构建基块。
• Processes for the preparation of hydroxyl-containing compounds
  申请人：UNION CARBIDE CHEMICALS AND PLASTICS COMPANY, INC.

  公开号：EP0478076A2

  公开（公告）日：1992-04-01

  A process for preparing hydroxyl-containing compounds which comprises contacting a carboxylated hydroxyl-containing compound with a metal oxide catalyst under conditions effective to produce the hydroxyl-containing compound.

  一种制备含羟基化合物的工艺，包括将羧化的含羟基化合物与金属氧化物催化剂在有效的条件下接触，以产生含羟基化合物。
• LOW VISCOSITY FUNCTIONAL FLUID COMPOSITION
  申请人：Clariant International Ltd

  公开号：EP3929269A1

  公开（公告）日：2021-12-29

  This invention relates to a functional fluid, comprising (A) from 70 to 90, preferably 75 - 87 wt.-% of alkoxy glycol according to formula (I)          CH3 - O - (CH2 - CH2 - O)n -H     (I) wherein n is a number from 2 to 5, with the proviso that in at least 30 wt.-% of all compounds according to formula (I) n is 3, and (B) less than 1.0 wt.-% of alkoxy glycol according to formula (II)          R1 - O - (CH2 - CH2 - O)m - H     (II) wherein R1 is a C2 to C8 alkyl residue, m is a number from 2 to 6, (C) from 8 to 25, preferably 12 - 23 wt.-% of at least one compound according to formula (III)          H - O - (CH2 - CH2 - O)k - H     (III) wherein k is a number of 2 or higher, with the proviso that in at least 80 wt.-% of all compounds according to formula (III) k is 2 or 3, (D) from 0.4 to 6 wt.-% of at least one additive, selected from the group consisting of corrosion inhibitors, alkalinity agents, aging protection agents, defoamers and lubricants, the fluid comprising at most 3 wt.-% of an ester between boric acid and a glycol or alkyl polyglycol compound.

  本发明涉及一种功能性流体，包括 (A) 70 至 90%，最好是 75 至 87 wt.-%的式 (I) 烷氧基乙二醇 CH3 - O - (CH2 - CH2 - O)n -H (I) 其中 n 是 2 至 5 的数字，但在所有符合式 (I) 的化合物中至少有 30% 的 n 是 3，以及 (B) 少于 1.0 重量-%的根据式(II)的烷氧基乙二醇 R1 - O - (CH2 - CH2 - O)m - H (II) 其中 R1 是 C2 至 C8 烷基残基、 m 是 2 至 6 的数字、 (C) 8-25%，最好是 12-23%的至少一种符合式(III)的化合物 H - O - (CH2 - CH2 - O)k - H (III) 其中 k 为 2 或更大的数字，但至少 80 重量-%的所有根据式(III)的化合物 k 为 2 或 3、 (D) 0.4 至 6 wt.-%的至少一种添加剂，选自腐蚀抑制剂、碱度剂、老化保护剂、消 泡剂和润滑剂组成的组，该流体包含至多 3 wt.-%的硼酸与乙二醇或烷基聚乙二醇化合物 之间的酯。