myristyl triflate | 157999-26-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: myristyl triflate
• 英文别名: Methanesulfonic acid, trifluoro-, tetradecyl ester；tetradecyl trifluoromethanesulfonate
• CAS: 157999-26-3
• 化学式: C₁₅H₂₉F₃O₃S
• 分子量: 346.455
• InChiKey: BJKCECIIUBWEEV-UHFFFAOYSA-N

物化性质

• 沸点：
  351.4±37.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  22
• 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：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  myristyl triflate 在 1,8-双二甲氨基萘 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 96.0h， 生成 2-myristyloxy-3-lauryloxypropylamine
  参考文献：
  名称：

  Synthesis of Novel Cationic Lipids:  Effect of Structural Modification on the Efficiency of Gene Transfer

  摘要：

  A series of novel cationic lipids was designed and synthesized in an effort to understand the importance of the various structural features with respect to transfection efficiency. Particular attention has been paid to the hydrophobic domain and the cationic headgroup. An efficient method of synthesizing asymmetric diether lipids is described, using alkyl chains ranging from C-12 to C-18 and the unsaturated oleyl group. The ternary formulations including the diether lipid 3beta-[N-(N',N'-dimethylaminoethyl)carbamoyl]cholesterol (DC-Chol) and dioleoyl phosphatidylethanolamine (DOPE) were up to 10-fold more efficacious in in vitro assays than the DC-Chol/DOPE control. The shorter and most asymmetric diether lipids performed the best. The chemical nature and basicity of the headgroups have been varied by the coupling of the four naturally occurring amino acids with cationic side chains-arginine, histidine, lysine, and tryptophan. Transfection efficiency was highest for arginine/lysine derivatives, with binary formulations containing the amino acid derivative alone and,DOPE proving superior.

  DOI：

  10.1021/jm010918g
• 作为产物：
  描述：

  十四醇 、 三氟甲磺酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 myristyl triflate
  参考文献：
  名称：

  烷基三氟甲磺酸酯与主要烷基格氏试剂的改进的铜催化交叉偶联反应

  摘要：

  金属催化的交叉偶联反应是强大的碳-碳键形成过程，在过去的三十年中受到了极大的关注。这种方法已被广泛用作合成各种天然产物、生物活性化合物和许多其他高度复杂的有机精细化学品的便捷工具？该方法包括甲苯磺酸盐与格氏试剂的反应，由不同金属催化，从昂贵且生理学上可疑的贵金属到廉价且毒理学上无害的铁盐？这种方法的主要限制是甲苯磺酸盐的置换通常需要剧烈的反应条件。三氟甲磺酸酯已被认为是溶剂分解置换反应中反应性最强的离去基团之一，并且在与炔基锂试剂的交叉偶联反应中确实显示出比相应的甲苯磺酸酯高得多的活性？这表明三氟甲磺酸酯应该更容易与有机金属亲核试剂偶联，因此将扩大可参与交叉偶联反应的缺电子底物的范围。如前所述，“甲苯磺酸盐与格氏试剂的交叉偶联反应已通过使用铜催化剂四氯铜酸二锂（Li，CuCl，）得到改善。已经报道了在相同条件下用三氟甲磺酸盐代替甲苯磺酸盐的尝试；然而，需要存在等摩尔量的溴化亚铜 (CuBr)

  DOI：

  10.1080/00304940809458090

文献信息

• Cross-linked polymer
  申请人：MITSUI CHEMICALS, INC.

  公开号：EP0856539A1

  公开（公告）日：1998-08-05

  A cross-linked polymer containing, in its molecule, recurring units represented by the following formula (1), and having biodegradability and high water-absorbency: wherein R1 is a pendant group having at least one functional group selected from the group consisting of acidic groups and salts thereof, a glycino group and salts thereof, cationic groups and betaine groups; X1 is NH, NR1', R1' being an alkyl, aralkyl or aryl group, O or S; and n1 is 1 or 2.

  一种交联聚合物，其分子中含有下式(1)所代表的循环单元，并具有生物降解性和高吸水性： 其中，R1 是具有至少一个官能团的悬垂基团，该官能团选自由酸性基团及其盐、甘氨酸基团及其盐、阳离子基团和甜菜碱基团组成的组；X1 是 NH、NR1'，R1' 是烷基、芳烷基或芳基、O 或 S；n1 是 1 或 2。
• Synthesis of Chiral Diether and Tetraether Phospholipids: Regiospecific Ring Opening of Epoxy Alcohol Intermediates Derived from Asymmetric Epoxidation
  作者：David H. Thompson、Chris B. Svendsen、Ciro Di Meglio、Valerie C. Anderson

  DOI：10.1021/jo00090a011

  日期：1994.6

  Diether and tetraether phospholipids have been synthesized using chiral epoxy alcohol starting materials (e.g. glycidol 3-nitrobenzenesulfonate esters or tert-butyldiphenylsilyl ethers). These chiral precursors provide control over the stereochemistry, substitution patterns, and steric properties of the phosphoglycerol backbone. Configuration at the sn-2 glycerol carbon was controlled by asymmetric epoxidation of allyl alcohol followed by acid-catalyzed, regioselective: Opening of the oxirane ring using excess aliphatic n-alcohols to give mono-O-alkylated glycerol intermediates in good yields. Nucleophilic attack at the less-hindered carbon of the oxirane ring was highly favored over attack at the sterically less accessible site, typically proceeding with regioselectivities of >10:1 and >95% ee's. Triflic acid, boron trifluoride etherate, toluenesulfonic acid, and tropylium tetrafluoroborate, all at 10 mol %, proved to be the most-effective catalysts compared with 10 % cesium fluoride, 10% magnesium chloride, or 20% DDQ based on (i) comparison of initial rates of product formation, (ii) regioselectivity of attack on the glycidol nucleus, and (iii) isolated yields of 3-O-alkyl-sn-glycerol 1-(3'-nitrobenzenesulfonates). Ether linked phospholipids, produced by alkylation of O-alkylglycerol sulfonates with excess n-alkyl triflates in the presence of equimolar 1,8-bis(dimethylamino)naphthalene, were isolated in 43-49 % overall yields (from glycidol 3-nitrobenzenesulfonate) after tetrabutylammonium hydroxide deprotection and phosphorylation; treatment of the 3-O-alkylglycerol sulfonates with tetrabutylammonium hydroxide prior to alkylation at the sn-2 center led to internal displacement and oxirane ring reformation, rather than hydrolysis to 3-O-alkylglycerol as described in J. Chromatogr. 1990, 506, 611. 3,3'-O-Polymethylene diglycerol phospholipids (bolaamphiphiles) were also prepared by this route using glycidol 3-nitrobenzenesulfonate and bifunctional alpha,omega-diols as nucleophiles. Synthesis of sterically demanding ether lipids, via Sharpless epoxidation of cyclopentene-1-methanol, produced materials that exhibited larger molecular areas than the analogous 1,2-di-O-alkylphosphatidic acids in monolayer experiments, confirming the restricted conformational flexibility of the cyclopentyl derivative at the air-water interface. Bolammphiphiles adopted a U-shaped conformation at the air-water interface. Elution-mode HPLC of racemic 3-O-hexadecyl-2-O-[(3',5'-dinitrophenyl) carbamoyl]glycerol 1-(3'-nitrobenzenesulfonate) on chiral naphthylalanine phases suggests that displacement-mode HPLC (Camacho-Torralba, P. L.; Vigh, G.; Thompson, D. H.; J. Chromatogr. 1993, 641, 31; 1993, 646, 259) may be used to obviate semipreparative chiral syntheses of alkyl glycerol ethers such as platelet activating factors, the antitumor agent ET-18-OCH3, and other biologically active ether lipids.
• Synthesis of D-erythro-sphingosine and D-erythro-sphinganine via 3-ketosphinganine
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1016/s0040-4039(98)00733-3

  日期：1998.6

  D-erythro-sphingosine and D-erythro-sphinganine can be produced in protected form from serine by a synthetic approach in which the normal biological intermediate 3-ketosphinganine in protectyed form, is a key synthetic intermediate. The sequence is short and convergent, proceeds in goad overall yields (approximate to 30% for 6 steps) and with excellent stereocontrol (>91% de, >95% ee). (C) 1998 Elsevier Science Ltd. All rights reserved.
• A Synthesis of <scp>d</scp>-<i>erythro</i>- and <scp>l</scp>-<i>threo</i>-Sphingosine and Sphinganine Diastereomers via the Biomimetic Precursor 3-Ketosphinganine
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1021/jo980003i

  日期：1998.6.1

  The four stereoisomers of sphingosine and sphinganine can be produced in protected form by a short, convergent, biomimetic synthesis from serine. Yields are good (26-38% overall from commercially available serine derivatives), and the stereoselectivities are excellent (>92% de, >95% eel. Several sphingosine L-threo-sphingosine analogues with modified, functionalized tails were prepared to demonstrate the versatility of the method.
• US5986042A
  申请人：——

  公开号：US5986042A

  公开（公告）日：1999-11-16