((Z)-9-octadecen-1-yl) triflate | 259738-67-5

• 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: ((Z)-9-octadecen-1-yl) triflate
• 英文别名: oleyl triflate；serachyl triflate；[(Z)-octadec-9-enyl] trifluoromethanesulfonate
• CAS: 259738-67-5
• 化学式: C₁₉H₃₅F₃O₃S
• 分子量: 400.546
• InChiKey: NBYJDNHMZHEKNC-KTKRTIGZSA-N

物化性质

• 沸点：
  420.9±45.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  ((Z)-9-octadecen-1-yl) triflate 在 sodium hydride 、 sodium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， 反应 20.5h， 生成 1-oleyloxy-3-oleyloxy(methoxy)methoxy-N,N,N-trimethyl-2-propanammonium chloride
  参考文献：
  名称：

  Novel pH-sensitive cationic lipids with linear ortho ester linkers for gene delivery

  摘要：

  In an effort to develop pH-sensitive lipoplexes for efficient gene delivery, we report three novel cationic lipids containing a linear ortho ester linker that conjugates either the headgroup (Type I) or one hydrocarbon chain (Type II) with the rest of the lipid molecule. The cationic lipids carry either an iodide or a chloride counterion. Compared to our previously reported cyclic ortho ester linker, the linear ortho ester linker facilitated the construction of cationic liposomes and lipoplexes with different helper lipids. The chloride counterion not only facilitated the hydration of the lipid films during liposome construction, but also enhanced the hydrolysis of the ortho ester linker in the lipoplexes. After incubation at endosomal pH 5.5, the Type I lipoplexes aggregated and destabilized the endosome-mimicking model liposomes, but not the Type II lipoplexes. The helper lipids (DOPE or cholesterol) of the lipoplexes enhanced the pH-sensitivity of the Type I lipoplexes. In CV-1 cells (monkey kidney fibroblast), the Type I ortho ester-based lipoplexes, especially those with the chloride counterion, significantly improved the gene transfection efficiency, in some cases by more than 100 fold, compared to their pH-insensitive counterparts consisting of DOTAP. The gene transfection efficiency of the ortho ester-based lipoplexes was well correlated with their rate of aggregation and membrane destabilization in response to the endosomal pH 5.5. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.013
• 作为产物：
  描述：

  油醇 、 三氟甲磺酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 ((Z)-9-octadecen-1-yl) triflate
  参考文献：
  名称：

  使烷基铪盐在铜催化交叉偶联反应中的应用成为可能

  摘要：

  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。

  DOI：

  10.1002/anie.202109723

文献信息

• Vinyl ether lipids with cleavable hydrophlic headgroups
  申请人：Thompson David H.

  公开号：US06979460B1

  公开（公告）日：2005-12-27

  A novel amphiphilic lipid compound having a cleavable, vinyl ether linked hydrophilic headgroup is described. Also described are liposomes containing the vinyl ether lipid compound, which may be triggered to release their contents and/or permeablize or fuse with target lipid membranes. The cleavable vinyl ether linkage allows the hydrophilic headgroup to be dissociated from the hydrophobic tailgroup(s) of the lipid compound to facilitate phase transitions in the lipid bilayer.

  描述了一种具有可切割的乙烯醚连接的亲水头基的新型两性脂质化合物。还描述了含有乙烯醚脂质化合物的脂质体，可以被触发释放其内容物和/或使目标脂质膜通透或融合。可切割的乙烯醚连接允许将亲水头基与脂质化合物的疏水尾基分离，以促进脂质双分子层中的相变。
• AMPHIPHILIC DERIVATIVES OF TRIAZAMACROCYCLIC COMPOUNDS, PRODUCTS AND COMPOSITIONS INCLUDING SAME, AND SYNTHESIS METHODS AND USES THEREOF
  申请人：BIOCELLCHALLENGE

  公开号：US20150353514A1

  公开（公告）日：2015-12-10

  The invention relates to amphiphilic derivatives of a triazamacrocyclic compound, as well as to said derivatives as active molecule transporters. The invention also relates to a nanodrug including at least one amphiphilic derivative of a triazamacrocyclic compound and at least one active molecule of a protein such as an antibody, in particular for the treatment of autoimmune diseases or for the treatment of cancer.

  这项发明涉及一种三氮杂大环化合物的两性衍生物，以及作为活性分子载体的这些衍生物。该发明还涉及一种纳米药物，包括至少一种三氮杂大环化合物的两性衍生物和至少一种蛋白质活性分子，如抗体，特别用于治疗自身免疫疾病或癌症的治疗。
• Practical Enantiospecific Syntheses of Lysobisphosphatidic Acid and Its Analogues
  作者：Guowei Jiang、Yong Xu、Glenn D. Prestwich

  DOI：10.1021/jo051894e

  日期：2006.2.1

  We describe a versatile, efficient, and practical method for the preparation of enantiomerically pure lysobisphosphatidic acid (LBPA), bisether analogues, and phosphorothioate analogues of LBPA from solketal. Phosphorylation of a protected sn-2-O-oleoyl glycerol with 2-cyanoethyl bis(N,N-diisopropylamino)phosphite, followed by oxidation and deprotection, generated the enantiomers of 2,2‘-LBPA. The

  我们描述了一种从Solketal制备对映体纯的lysobisphosphatidic acid（LBPA），双醚类似物和LBPA的硫代磷酸酯类似物的通用，有效和实用的方法。受保护的磷酸化SN -2- ø -油酰基甘油与2-氰基乙基双（Ñ，Ñ -diisopropylamino）亚磷酸酯，然后氧化和脱保护，生成2,2'- LBPA的对映体。通过用硫氧化获得相应的硫代磷酸酯类似物。LBPA和硫代磷酸LBPA的（R，R）和（S，S）对映体由（S）-和（R）-solketal。通过简单地改变去保护步骤的顺序，由相同的对映异构体（S）-缩酮合成（S，S）-溶血双磷脂酸（LBPA）的醚类似物及其对映异构体。
• Synthesis of Novel Cationic Lipids:  Effect of Structural Modification on the Efficiency of Gene Transfer
  作者：James A. Heyes、Dan Niculescu-Duvaz、Robert G. Cooper、Caroline J. Springer

  DOI：10.1021/jm010918g

  日期：2002.1.1

  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.
• Concise Synthesis of Ether Analogues of Lysobisphosphatidic Acid
  作者：Guowei Jiang、Yong Xu、Thomas Falguières、Jean Gruenberg、Glenn D. Prestwich

  DOI：10.1021/ol051194w

  日期：2005.9.1

  We describe a versatile, efficient method for the preparation of ether analogues of (SS)-lysobisphosphatidic acid (LBPA) and its enantiomer from (S)-solketal. Phosphorylation of a protected sn-2-O-octadecenyl glyceryl ether with 2-cyanoethyl bis-N,N-diisopropylamino phosphine and subsequent deprotection generated the bisether LBPA analogues. By simply changing the sequence of deprotection steps, we obtained the (R,R)- and (SS)-enantiomers of 2,2'-bisether LBPA. An ELISA assay with anti-LBPA monoclonal antibodies showed that the bisether LBPAs were recognized with the same affinity as the natural 2,2'-bisoleolyl LBPA.