[(十八烷氧基)甲基]环氧乙烷 | 16245-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: [(十八烷氧基)甲基]环氧乙烷
• 英文名称: octadecyl glycidyl ether
• 英文别名: stearyl glycidyl ether；rac-1,2-epoxy-3-octadecyloxypropane；[(Octadecyloxy)methyl]oxirane；2-(octadecoxymethyl)oxirane
• CAS: 16245-97-9
• 化学式: C₂₁H₄₂O₂
• 分子量: 326.563
• InChiKey: ZXJBWUAALADCRI-UHFFFAOYSA-N

物化性质

• 熔点：
  38-39 °C
• 沸点：
  202-207 °C(Press: 3 Torr)
• 密度：
  0.885±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  23
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2910900090

反应信息

• 作为反应物：
  描述：

  [(十八烷氧基)甲基]环氧乙烷 在 高氯酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 鲨肝醇
  参考文献：
  名称：

  Synthesis of 1-O-Alkyl-2-O-Acetyl-Sn-3-glyceryl-3-phosphoryl Choline the Enantiomer of Platelet Activating Factor (PAF)

  摘要：

  DOI：

  10.1080/00397919108021574
• 作为产物：
  描述：

  鲨肝醇 在 吡啶 、 盐酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 氯仿 为溶剂， 生成 [(十八烷氧基)甲基]环氧乙烷
  参考文献：
  名称：

  甘油醚磷脂的合成第1部分1 - O-十八烷基-2- O-乙酰基-sn-甘油-3-磷酸胆碱1（“血小板活化因子”），对映异构体和一些类似化合物的生产† ‡

  摘要：

  甘油醚磷脂的合成，第一次通讯，对映体和一些类似化合物的1- O-十八烷基-2- O-乙酰基-sn-甘油-3-磷酸胆碱（“血小板活化因子”）的制备

  DOI：

  10.1002/hlca.19820650339
• 作为试剂：
  描述：

  dibutyltin(II) dilaurate 、 氨基甲酸乙酯 以 [(十八烷氧基)甲基]环氧乙烷 为溶剂， 生成 5-stearyloxymethyl-2-oxazolidinone
  参考文献：
  名称：

  5-substituted 2-oxazolidinones

  摘要：

  5-烷氧甲基或烯基氧甲基-2-噁唑啉，特别是具有长链烷基或烯基基团的化合物，在聚脲反应注射成型技术中作为内部脱模剂是有用的。

  公开号：

  US05268484A1

文献信息

• Synthesis and antitumor activity of new amphiphilic alkylglycerolipids substituted with a polar head group, 2-(2-trimethylammonioethoxy)ethyl or a congeneric oligo(ethyleneoxy)ethyl group.
  作者：Kiyoshi UKAWA、Eiko IMAMIYA、HIroaki YAMAMOTO、Tetsuya AONO、Yoshio KOZAI、Tetsuya OKUTANI、Hiroaki NOMURA、Yoshio HONMA、Motoo HOZUMI、Ichiro KUDO、Keizo INOUE

  DOI：10.1248/cpb.37.3277

  日期：——

  A new series of amphiphilic 1-octadecyl glycerolipids (eleven compounds, 1a-k) were designed and synthesized, in which the 3-phosphocholine portion of platelet-activating factor (1-alkyl-2-acetyl-sn-glycero-3-phosphocholine, PAF) was replaced by the 2-(2-trimethylammonioethoxy)ethyl group and congeneric groups having oligo(ethyleneoxy)ethyl bridges of various lengths at position 3, together with modification at position 2 (lower alkyl, acetonyl, acetoacetyl, carboxymethyl and pyrimidin-2-yl groups). These ether lipids, characterized by a nonphosphorus lysoglycerolipid structure, showed potent antitumor activity in vitro (human promyelocytic leukemia cells, HL-60, and human epidermoid carcinoma cells, KB) and in vivo (mouse sarcoma S180 and mouse mammary carcinoma MM46). Maximal in vitro potency was obtained with 1-O-octadecyl-2-O-(2-pyrimidinyl)-3-O-[2-(2-trimethylammonioethoxy)ethyl]glycerol (1g; IC50 values for both HL-60 and KB were 0.32 μg/ml, indicating a higher activity than alkyl-lysophospholipid, ET18-OMe). Several appropriately 2-substituted 1-octadecylglycerolipids with the 3-[2-(2-trimethylammonioethoxy)ethyl]group (e.g., methyl, 1b; butyl, 1f; 2, 2, 2-trifluoroethyl, 1g; and acetonyl, 1k) showed a potent life-span-prolonging effect on mice with ascites sarcoma S180 and on those with mammary carcinoma MM46, when administered intraperitoneally at 16.5 and 12.5 mg/kg/d, respectively. Compounds 1b and 1k showed definite tumor growth inhibition against solid sarcoma S180 in mice, whether given p.o. or i.v. at 16.5 gm/kg/d. Studies on the structure-activity relationships indicate that the metabolic stability to phospholipase C or related enzymes is at least partly responsible for the potent antitumor activity of this series of ether lipids.

  设计并合成了一系列新型的十八烷基甘油醚脂（11个化合物，1a-k），其中血小板活化因子（1-烷基-2-乙酰基-sn-甘油-3-磷酸胆碱，PAF）的3-磷酸胆碱部分被2-（2-三甲基铵乙氧基）乙基和连接在3位的不同长度的聚（乙二醇）乙基桥的同系物所替代，同时在2位进行了修饰（低级烷基、乙酮基、乙酰乙酰基、羧甲基和吡啶-2-基等基团）。这些具有无磷酸的溶血甘油醚脂结构的醚脂，在体外（人早幼粒白血病细胞HL-60和人表皮癌KB细胞）和体内（小鼠肉瘤S180和小鼠乳腺癌MM46）均显示出强大的抗癌活性。其中，1-O-十八烷基-2-O-（2-吡啶基）-3-O-[2-（2-三甲基铵乙氧基）乙基]甘油（1g；IC50值，HL-60和KB均为0.32 μg/ml）显示最高的体外活性，超过了烷基溶血磷脂ET18-OMe。几个在2位适当修饰的1-十八烷基甘油醚脂，带有3-[2-（2-三甲基铵乙氧基）乙基]基团（例如，甲基，1b；丁基，1f；2,2,2-三氟乙基，1g；和乙酮基，1k）对腹水型肉瘤S180小鼠和乳腺癌MM46小鼠显示出强大的延命效果，分别以16.5和12.5 mg/kg/d的剂量腹腔注射给予。化合物1b和1k对实体型肉瘤S180小鼠显示出确定的肿瘤生长抑制效果，无论口服还是静脉注射给药，剂量均为16.5 gm/kg/d。结构-活性关系的研究表明，这一系列醚脂的强大抗癌活性至少部分归因于它们对磷脂酶C或相关酶的代谢稳定性。
• Production processes for triorganomonoalkoxysilanes and triorganomonochlorosilanes
  申请人：Bannou Tadashi

  公开号：US20050070730A1

  公开（公告）日：2005-03-31

  A silane containing a bulky hydrocarbon group or groups R therein and having the formula (III) R 3-(x+y) (R 1 ) x (R 2 ) y Si(OR 3 ) can be produced by reacting a silane of the formula (I) (R 1 ) x (R 2 ) y SiCl 3-(x+y) (OR 3 ) with a Grignard reagent of the formula (II) RMgX Further, a tri-organo-chlorosilane of the formula (XIIa) (R 1 )(R 2 )(R 3 )SiCl can be produced by reacting a tri-organo-silane of the formula (XIa) (R 1 )(R 2 )(R 3 )SiZ 1 with hydrochloric acid. Furthermore, a tri-organo-monoalkoxysilane of the formula (XXIII) R 3-(x+y) (R 1 ) x (R 2 ) y Si(OR 3 ) can be produced when a silane of the formula (XXI) (R 1 ) x (R 2 ) y SiCl 4-(x+y) is reacted with a Grignard reagent of the formula (XXII) RMgX with addition of and reaction with an alcohol or an epoxy compound during the reaction.

  含有庞大烃基或基团R的硅烷，其具有式(III)R3-(x+y)(R1)x(R2)ySi(OR3)，可通过反应式(I)(R1)x(R2)ySiCl3-(x+y)(OR3)的硅烷与式(II)RMgX的格氏试剂制得。此外，式(XIIa)(R1)(R2)(R3)SiCl的三有机氯硅烷可通过反应式(XIa)(R1)(R2)(R3)SiZ1的三有机硅烷与盐酸制得。再者，当式(XXI)(R1)x(R2)ySiCl4-(x+y)的硅烷与式(XXII)RMgX的格氏试剂反应，并在反应过程中加入并反应酒精或环氧化合物时，可制得式(XXIII)R3-(x+y)(R1)x(R2)ySi(OR3)的三有机单烷氧基硅烷。
• [EN] REACTIVE SURFACTANTS<br/>[FR] TENSIOACTIFS RÉACTIFS
  申请人：STEPAN CO

  公开号：WO2020185513A1

  公开（公告）日：2020-09-17

  Processes for making reactive surfactants are disclosed. In one such process, a fatty epoxide, a glycidyl ether, or a combination thereof is reacted with an olefin-functional nucleophile to produce an olefin-functional hydrophobe. The olefin-functional hydrophobe is reacted with ethylene oxide, propylene oxide, butylene oxides, or a combination thereof to produce an alkoxylate. Optionally, the alkoxylate is converted to the corresponding sulfate, phosphate, or maleate. Surfactant compositions comprising the reactive surfactants made by these processes are also described. The invention includes polymerizable mixtures comprising an acrylic monomer and the surfactant compositions as well as aqueous acrylic latex emulsions and coatings produced from the emulsions. The reactive surfactants deliver stable latex emulsions with reduced tendency for surfactant migration or excessive foaming. Coatings from the emulsions have improved wet adhesion, scrub resistance, and water resistance.

  揭示了制备反应性表面活性剂的方法。在其中一种方法中，脂肪环氧化物、环氧乙醚或二者的组合物与烯烃官能核糖核发生反应，从而产生烯烃官能亲水基。将烯烃官能亲水基与环氧乙烷、丙烯酸丙烯酯、丁烯氧化物或二者的组合物发生反应，制备烷氧基化物。可选地，将烷氧基化物转化为相应的硫酸盐、磷酸盐或马来酸盐。还描述了由这些方法制备的含有反应性表面活性剂的表面活性剂组合物。该发明还包括包含丙烯酸单体和表面活性剂组合物的可聚合混合物，以及由这些乳液制备的水性丙烯酸乳胶乳液和涂料。反应性表面活性剂可提供稳定的乳胶乳液，减少表面活性剂迁移或过度起泡的倾向。从这些乳液中制备的涂料具有改善的湿附着力、耐擦洗性和耐水性。
• Antimicrobial medicotechnical product, process for its production and use
  申请人：Edermatt Erich

  公开号：US20080292675A1

  公开（公告）日：2008-11-27

  The invention relates to a medicotechnical product having an antimicrobial finish consisting of a complex material of metal nanoparticles and macromolecules, the macromolecules being at least partially formed from amphiphilically modified polyamino acids which contain amino acid units, which aside from the functional groups bonded in the peptide bond contain at least one further functional group and at least some of these groups are modified with substances bearing hydrophobic radicals via covalent bonds. The hydrophobic radicals are bonded by addition of substances bearing epoxy groups to the at least one further functional group and/or via at least one amino group of an amino acid unit bearing at least one amino group as a further functional group with maintenance of an amino function on the polyamino acids. The invention furthermore relates to the production of the complex material and of the medicotechnical product.

  该发明涉及一种医学技术产品，具有抗菌涂层，该涂层由金属纳米粒子和大分子复合材料组成，其中这些大分子至少部分由含有氨基酸单元的两性修饰聚氨基酸形成，除了在肽键中结合的功能基团外，还包含至少一个进一步的功能基团，其中至少一些这些基团通过共价键与含有疏水基团的物质修饰。这些疏水基团通过将含有环氧基团的物质添加到至少一个进一步的功能基团和/或通过至少一个含有至少一个氨基的氨基酸单元上的氨基团之间结合，同时保持聚氨基酸上的氨基功能。该发明还涉及复合材料和医学技术产品的生产。
• Synthesis of Highly Fluorinated Di-O-alk(en)yl-glycerophospholipids and Evaluation of Their Biological Tolerance
  作者：V�ronique Ravily、Sylvie Gaentzler、Catherine Santaella、Pierre Vierling

  DOI：10.1002/hlca.19960790209

  日期：1996.3.20

  The syntheses of various fluorocarbon/fluorocarbon and fluorocarbon/hydrocarbon rac-1,2- and 1,3-di-O-alk(en)ylglycerophosphocholines and rac-1,2-di-O-alkylglycerophosphoethanolamines (see Fig.2), which may be used as components for drug-carrier and delivery systems, are described together with some results concerning their biological tolerance. They were obtained by phosphorylation of perfluoroalkylated

  各种碳氟化合物的合成/碳氟化合物和碳氟化合物/烃外消旋-1,2-和1,3-二- Ö -Alk（烯）ylglycerophosphocholines和外消旋-1,2-二- Ö -alkylglycerophosphoethanolamines（参见图2），描述了可以用作药物载体和递送系统组件的药物，以及有关其生物学耐受性的一些结果。他们由全氟烷基化的磷酸化得到的外消旋-二- ø -Alk（烯）使用的POCl ylgly-cerols 3，然后缩合胆碱甲苯磺酸酯或ñ -Boc -乙醇胺（2 - [（叔丁氧基）羰基氨基]乙醇）其次是Boc-deportection（方案6-8）。所述氟碳/氟1,2-二- ö -alkylgly-cerols通过制备Ó的烷基化的外消旋-1- ö -benzylglycerol使用全氟烷基甲磺酸酯，然后氢解苄基的脱保护（方案1）。在混合的碳氟化合物的两种不同的疏水链/碳氟化合物和碳氟化合物/烃1