1-octadecyl trifluoromethanesulfonate | 76679-48-6

• 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: 1-octadecyl trifluoromethanesulfonate
• 英文别名: n-octadecyl triflate；Octadecyl triflate；octadecyltryflate；stearyl triflate；octadecyl trifluoromethanesulfonate
• CAS: 76679-48-6
• 化学式: C₁₉H₃₇F₃O₃S
• 分子量: 402.562
• InChiKey: OGLOUCVTUZYEGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  411.2±40.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  26
• 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：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-octadecyl trifluoromethanesulfonate 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-stearyloxy-3-palmityloxypropylamine
  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：

  硬脂醇 、 三氟甲磺酸酐 以 氯仿 为溶剂， 反应 4.0h， 以89%的产率得到1-octadecyl trifluoromethanesulfonate
  参考文献：
  名称：

  通过静电自组装进行表面改性，然后进行共价固定

  摘要：

  黏合：表面改性剂可以用离子基团官能化，从而可以通过静电自组装从处理槽中大量排出。通过使用环状鎓作为离子官能团，热诱导的开环将离子键转换为共价键，从而使表面持久化。

  DOI：

  10.1002/anie.201106968

文献信息

• Enabling the Use of Alkyl Thianthrenium Salts in Cross‐Coupling Reactions by Copper Catalysis
  作者：Cheng Chen、Minyan Wang、Hongjian Lu、Binlin Zhao、Zhuangzhi Shi

  DOI：10.1002/anie.202109723

  日期：2021.9.27

  used groups in organic synthesis. Here, a a series of thianthrenium salts have been synthesized that act as reliable alkylation reagents and readily engage in copper-catalyzed Sonogashira reactions to build C(sp3)−C(sp) bonds under mild photochemical conditions. Diverse alkyl thianthrenium salts, including methyl and disubstituted thianthrenium salts, are employed with great functional breadth, since

  烷基是有机合成中应用最广泛的基团之一。在这里，已经合成了一系列的铪盐，它们作为可靠的烷基化试剂，可以很容易地参与铜催化的 Sonogashira 反应，在温和的光化学条件下建立 C(sp 3 )-C(sp) 键。由于敏感的 Cl、Br 和 I 原子在常规方法中耐受性差，因此可以使用多种烷基铪盐，包括甲基和双取代的铪盐，具有很大的功能广度。在铜催化的熊田反应中也证明了所开发的烷基试剂的通用性。
• Amphiphilic Long-chain Citric Acid Ethers
  作者：Daniel Meißner、Peter Jutzi

  DOI：10.1515/znb-2009-0620

  日期：2009.6.1

  The etherification of the hydroxyl group of citric acid with saturated and unsaturated long-chain alkyl groups is described. This is a new approach to polydentate acids which may serve as ligands for metal or metal oxide nanoparticles. For this purpose we developed a synthetic route to long-chain ω-unsaturated alcohols and their triflate derivatives.

  描述了柠檬酸羟基与饱和和不饱和长链烷基基团的醚化反应。这是一种新的制备多齿酸的方法，可以作为金属或金属氧化物纳米颗粒的配体。为此，我们开发了一种合成长链ω-不饱和醇及其三氟甲烷基衍生物的方法。
• Synthesis of α- and β-glycopyranosides via 1-0-alkylation
  作者：R.R. Schmidt、U. Moering、M. Reichrath

  DOI：10.1016/0040-4039(80)80236-x

  日期：1980.1

  1-0-Alkylation of partly protected glucopyranose 1 and galactopyranose 13 led to a convenient, short term synthesis of β-glycosides and β-disaccharides 4a–d and 14. Glucopyranose 2 with a bulky protective group at 0–6 yielded exclusively the α-anomer (isomaltoside derivative) 5.

  部分保护的吡喃葡萄糖1和半乳糖吡喃糖13的1-0烷基化导致β-糖苷和β-二糖4a-d和14的便捷，短期合成。在0-6带有较大保护基的葡糖醛糖2仅产生α。 -异头物（异麦芽糖苷衍生物）5。
• Novel photochromic spiro compounds based on thieno[3,2-<i>b</i>]pyrroles
  作者：Mikhail M. Krayushkin、Valerii Z. Shirinian、Alexey A. Shimkin、Arthur K. Mailian、Anatoly V. Metelitsa、Sergei O. Bezugliy

  DOI：10.1002/poc.1238

  日期：2007.11

  Previously unknown spiro compounds of thienopyrroline series were synthesized by a convenient method starting from easily accessible 3-hydroxythiophene derivatives. The photochromic properties of spiro compounds of thienopyrroline series were studied. Copyright © 2007 John Wiley & Sons, Ltd.

  通过方便的方法，从容易获得的3-羟基噻吩衍生物开始，合成了噻吩并吡咯啉系列的未知螺化合物。研究了噻吩并吡咯啉系列螺化合物的光致变色性质。版权所有©2007 John Wiley＆Sons，Ltd.
• Synthesis of spiropyrans and merocyanine dyes based on 1-benzothieno[3,2-b]pyrrole
  作者：A. A. Shimkin、V. Z. Shirinian、A. K. Mailyan、M. M. Krayushkin

  DOI：10.1007/s11172-010-0019-1

  日期：2009.2

  5]-sigmatropic rearrangement giving rise to 2H-[1]benzo-thieno[3,2-b]pyrrole derivatives. The latter compounds were used for the synthesis of the first representatives of the previously unknown spiro compounds and merocyanine dyes. The long-wavelength maxima of merocyanines of the 2H-benzothienopyrrole series are batho-chromically shifted by more than 100 nm with respect to the absorption maxima of the

  基于 Fischer 盐类似物的常规缩合，开发了一种方便的方法来合成 1-苯并噻吩并 [3,2-b] 吡咯啉系列的光致变色螺吡喃和部花青染料，即 1,2,3,3 -四甲基-3H-[1]苯并噻吩基-[3,2-b]吡咯三氟甲磺酸盐，带有芳香族2-羟基醛。与 Fischer 盐不同，苯并噻吩并吡咯鎓盐容易发生 [1,5]-σ 重排，产生 2H-[1] 苯并噻吩并 [3,2-b] 吡咯衍生物。后一种化合物用于合成先前未知的螺环化合物和部花青染料的第一个代表。相对于“经典”3H-苯并噻吩并吡咯类似物的吸收最大值，2H-苯并噻吩并吡咯系列的部花青的长波长最大值红移超过100 nm。