二聚乙二醇单癸醚 | 23238-41-7

• 物质功能分类: 催化剂及助剂 - 聚乙二醇衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 二聚乙二醇单癸醚
• 中文别名: 2-[2-(癸基氧基)乙氧基]乙醇
• 英文名称: Brij 92
• 英文别名: diethylene glycol monodecyl ether；2-<2-decyloxy)ethoxy>ethanol；2-(2-decyloxy-ethoxy)-ethanol；Lutensol ON 30；Diethylene glycol, decyl ether；2-(2-decoxyethoxy)ethanol
• CAS: 23238-41-7
• 化学式: C₁₄H₃₀O₃
• 分子量: 246.39
• InChiKey: UVNSFSOKRSZVEZ-UHFFFAOYSA-N

物化性质

• 密度：
  0.911 g/mL at 20 °C(lit.)
• 保留指数：
  1828.8

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2909499000

反应信息

• 作为反应物：
  描述：

  二聚乙二醇单癸醚 在 吡啶 、 Amberlyst-15 ion-exchange resin 、 sodium acetate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.75h， 生成 Phosphoric acid 2-benzyloxy-3-[2-(2-decyloxy-ethoxy)-ethoxy]-propyl ester 2-bromo-ethyl ester
  参考文献：
  名称：

  Analogs of platelet activating factor. 5. Multiple oxygen substitution of the alkoxy chain

  摘要：

  Racemic analogues of platelet activating factor (PAF) in which the alkoxy chain (R = -O(CH2)15CH3) has been replaced with a chain containing multiple ether linkages near the end (17, R = -O(CH2)8O(CH2)2O(CH2)2OCH3) or at the beginning (18, R = -O(CH2)2O(CH2)2O(CH2)9CH3) of the chain have been prepared. Both compounds exhibit reduced hypotensive and platelet aggregation responses compared to racemic C16-PAF (1a). This reduction in the biological activities is more apparent when the new oxygen atoms are located near the end of the chain. This substitution of additional oxygen atoms into the alkoxy chain does not result in any dramatic gains in selectivity of the biological responses.

  DOI：

  10.1021/jm00157a038
• 作为产物：
  描述：

  癸基溴 、 二乙二醇 在 sodium hydride 作用下， 生成 二聚乙二醇单癸醚
  参考文献：
  名称：

  Analogs of platelet activating factor. 5. Multiple oxygen substitution of the alkoxy chain

  摘要：

  Racemic analogues of platelet activating factor (PAF) in which the alkoxy chain (R = -O(CH2)15CH3) has been replaced with a chain containing multiple ether linkages near the end (17, R = -O(CH2)8O(CH2)2O(CH2)2OCH3) or at the beginning (18, R = -O(CH2)2O(CH2)2O(CH2)9CH3) of the chain have been prepared. Both compounds exhibit reduced hypotensive and platelet aggregation responses compared to racemic C16-PAF (1a). This reduction in the biological activities is more apparent when the new oxygen atoms are located near the end of the chain. This substitution of additional oxygen atoms into the alkoxy chain does not result in any dramatic gains in selectivity of the biological responses.

  DOI：

  10.1021/jm00157a038

文献信息

• Antihypertensive phosphate derivatives
  申请人：American Cyanamid Company

  公开号：US04703130A1

  公开（公告）日：1987-10-27

  Antihypertensive phosphate derivatives having the following formula are described: ##STR1## wherein W is selected from the group consisting of methyl and phenyl optionally substituted with C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and phenyl; r, n, m and a are integers such that the expression r+(n+1)m+a is also an integer and has a value of 3 to 20; r is greater than or equal to 2; n is greater than or equal to 2; m is greater than or equal to zero and a is greater than or equal to zero; T is selected from the group consisting of hydrogen and ##STR2## wherein R.sub.1 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 branched or straight chain alkyl, C.sub.1 -C.sub.4 branched or straight chain alkoxy and C.sub.1 -C.sub.4 branched or straight chain alkylamino; Q is a bivalent radical selected from --(CH.sub.2).sub.p -- and --(CHR).sub.p --, wherein p is an integer 2-12 and the moiety --(CHR).sub.p -- represents an alkylene chain which is substituted by one or more C.sub.1 -C.sub.10 alkyl groups or phenyl groups; Z is selected from the group consisting of ##STR3## wherein R.sub.2 may be the same or different and is selected from the group consisting of hydrogen and C.sub.1 -C.sub.4 branched or straight chain alkyl and q is an integer from 4-7; in either the racemic or optically active forms.

  描述具有以下公式的降压磷酸衍生物：##STR1## 其中W从由甲基和苯组成的基团中选择，该基团可以选择性地被C.sub.1 -C.sub.3烷基，C.sub.1 -C.sub.3烷氧基和苯基取代；r、n、m和a是整数，使得表达式r+(n+1)m+a也是整数，并且其值为3到20；r大于或等于2；n大于或等于2；m大于或等于零且a大于或等于零；T从氢和##STR2## 中选择，其中R.sub.1从氢，C.sub.1 -C.sub.4支链或直链烷基，C.sub.1 -C.sub.4支链或直链烷氧基和C.sub.1 -C.sub.4支链或直链烷基氨基组成的基团中选择；Q是从--(CH.sub.2).sub.p --和--(CHR).sub.p --中选择的二价基团，其中p是整数2-12，而基团--(CHR).sub.p --代表一个被一个或多个C.sub.1 -C.sub.10烷基或苯基取代的烷基链；Z从##STR3## 中选择，其中R.sub.2可以相同也可以不同，并且从氢和C.sub.1 -C.sub.4支链或直链烷基中选择，q是一个整数从4-7；可以是消旋的或光学活性形式。
• Surface Activity of Alkoxy Ethoxyethyl β-<scp>d</scp>-Glucopyranosides
  作者：Yulin Fan、Fang Fu、Langqiu Chen、Jiping Li、Jing Zhang

  DOI：10.1021/acs.jafc.9b05966

  日期：2020.3.4

  length. Hexadecoxy ethoxyethyl β-d-glucopyranoside had no water solubility at 25 °C. Decoxy ethoxyethyl β-d-glucopyranoside had the best emulsifying property in the toluene/water and n-octane/water systems and the strongest foaming property, whereas dodecoxy ethoxyethyl β-d-glucopyranoside had the best emulsifying property in the rapeseed oil/water system. Such β-d-glucopyranosides (n = 6-12) exhibited

  将二氧乙烯片段（-（OCH2CH2）2-）引入传统的烷基β-d-吡喃葡萄糖苷中以改善水溶性，并引入了八种非离子表面活性剂，即烷基链长为（n = 6-的烷氧基乙氧基乙基β-d-吡喃葡萄糖苷）。 16），进行了合成和表征。随着烷基链长度的增加，它们的亲水和亲脂平衡值，水溶性，临界胶束浓度（cmc），γcmc，Γmax和吸湿率降低。十六烷氧基乙氧基乙基β-d-吡喃葡萄糖苷在25℃下没有水溶性。脱氧乙氧基乙基β-d-吡喃葡萄糖苷在甲苯/水和正辛烷/水体系中具有最好的乳化性能和最强的起泡性能，而十二烷氧基乙基β-d-吡喃葡萄糖苷在菜籽油/水系统中具有最好的乳化性能。这种β-d-吡喃葡萄糖苷（n = 6-12）表现出优异的表面活性。此外，对于烷氧基乙氧基乙基β-d-吡喃葡萄糖苷（n = 8、10、12）和十二烷基硫酸钠或十六烷基三甲基氯化铵的二元混合物，其cmc值低于纯β-d-吡喃葡萄糖苷。他们具有协
• Water Solubility and Surface Property of Alkyl Di-/Tri-/Tetraoxyethyl β-<scp>d</scp>-Xylopyranosides
  作者：Xiubing Wu、Langqiu Chen、Yulin Fan、Fang Fu、Jiping Li、Jing Zhang

  DOI：10.1021/acs.jafc.9b03435

  日期：2019.9.18

  chain length and increasing the number of the oligooxyethyl fragment. The critical micelle concentration had a monotonous decreasing trend with increasing the alkyl chain length. Nonyl di-/tri-/tetraoxyethyl β-d-xylopyranosides [−(OCH2CH2)m–, where m = 2, 3, and 4] exhibited the most excellent foaming ability and foam stability. In the n-octane/water system, dodecyl tetraoxyethyl β-d-xylopyranosides and

  作为烷基木糖苷衍生物的烷基二-/三-/四氧基乙基β- d-吡喃吡喃糖苷是一类非离子的基于糖的表面活性剂。它们通过Helferich方法立体选择性地合成。主要研究了它们的性质，包括亲水-亲脂平衡值，水溶性，表面性质，泡沫性质，乳化性质和热致液晶性质。结果表明，它们的水溶性随着烷基链长度的增加和低聚氧乙基片段数量的增加而降低。随着烷基链长度的增加，临界胶束浓度呈单调下降趋势。壬基二-/三-/四氧基乙基β- d-吡喃吡喃糖苷[-（OCH 2 CH 2）m–，其中m = 2、3和4]表现出最出色的起泡能力和泡沫稳定性。在正辛烷/水体系中，十二烷基四氧乙基β- d-吡喃吡喃糖苷和十四烷基四氧乙基β- d-吡喃吡喃糖苷具有最强的乳化能力。另外，一些烷基二-/三-/四氧基乙基β- d-吡喃吡喃糖苷具有热致液晶特性。这样的基于糖的表面活性剂，烷基二-/三-/四氧基乙基β- d-吡喃吡喃糖苷，有望被开发用于多种实际应用。
• Synthesis and property of alkyl dioxyethyl α-D-xyloside
  作者：Xiubing Wu、Na Kuang、Langqiu Chen、Yulin Fan、Fang Fu、Jiping Li、Jing Zhang

  DOI：10.1016/j.molliq.2020.113770

  日期：2020.10

  of the long alkyl chain in the related hydrophilicity and water solubility, alkyl α-D-xylosides (7) had hardly the practical application as sugar-based surfactants and should be reconstructed to obtain alkyl dioxyethyl α-D-xylosides (5) with dioxyethylene fragment (−(OCH2CH2)2-)) as the hydrophilic spacer to increase the related TPSA value. With D-xylose as the raw material, 1,2-cis alkyl dioxyethyl

  由于长烷基链在亲水性和水溶性方面的固有缺陷，烷基α - D-木糖苷( 7 )作为糖基表面活性剂几乎没有实际应用，需要进行改造以获得烷基二氧乙基α - D-木糖苷( 5 )以二氧乙烯片段(-(OCH 2 CH 2 ) 2 -))作为亲水间隔基以增加相关的TPSA值。以D-木糖为原料，立体选择性合成了1,2-顺式烷基二氧乙基α - D-木糖苷（5a-5f ，n=6-12）。研究了它们的物理化学性质，包括水溶性、表面张力、发泡性、乳化性、热致液晶性和吸湿性。随着烷基链长度 (n)的增加，它们的水溶性逐渐降低，而计算出的HLB值为 14.72 → 11.67 (n = 6 → 12)。十二烷基二氧乙基α - D-木糖苷( 5f )由于HLB值低而不具有水溶性。此外，它们的CMC值随着烷基链长度的增加而降低，其中癸基二氧乙基α - D-木糖苷( 5e )的CMC值低至9.21×10 -5  mol·L
• Derivatization of fatty alcohol ethoxylate non-ionic surfactants using 2-sulfobenzoic anhydride for characterization by liquid chromatography/mass spectrometry
  作者：Chengli Zu、Herbert N. Praay、Bruce M. Bell、O. David Redwine

  DOI：10.1002/rcm.4367

  日期：——

  surfactant species was converted into an oxycarbonylbenzene-2-sulfonic acid group with 2-sulfobenzoic anhydride under mild conditions. The produced sulfonic acid group allows all species, including fatty alcohols and those with less than three ethoxylates, to be uniformly ionized by electrospray ionization (ESI) mass spectrometry. Both acid and base can be used as a mobile phase additive for liquid chromatography

  已经开发了衍生化方法，以通过液相色谱/质谱法改进脂肪醇乙氧基化物非离子表面活性剂的表征。在温和的条件下，用2-磺基苯甲酸酐将每种表面活性剂物种的末端羟基转化为氧羰基苯-2-磺酸基团。产生的磺酸基团允许通过电喷雾电离（ESI）质谱将所有种类（包括脂肪醇和少于三个乙氧基化物的种类）均匀地电离。酸和碱均可用作液相色谱的流动相添加剂，而不会影响M（n）和平均乙氧基化物值，尽管在ESI过程中离子强度受到抑制。该方法用于分析七种市售脂肪醇乙氧基化物非离子表面活性剂，测定的M（n）和EO值与NMR结果相当。样品中不同脂肪醇基乙氧基化物的相对比例也可以使用汇总质谱数据确定。