18,18,18-trifluorooctadecanoic acid | 408-34-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 18,18,18-trifluorooctadecanoic acid
• 英文别名: 18,18,18-trifluorostearic acid；18,18,18-trifluoro-octadecanoic acid；18,18,18-Trifluor-octadecansaeure；17-Trifluormethyl-heptadecansaeure
• CAS: 408-34-4
• 化学式: C₁₈H₃₃F₃O₂
• 分子量: 338.454
• InChiKey: HAUFUYBOCZLVDV-UHFFFAOYSA-N

物化性质

• 沸点：
  396.1±37.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)
• 熔点：
  70.0-70.5 °C(Solv: hexane (110-54-3))

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  18,18,18-trifluorooctadecanoic acid 在 sodium hydroxide 作用下， 生成 12,12,12-三氟十二烷酸
  参考文献：
  名称：

  Dissociative and Reactive Hyperthermal Ion−Surface Collisions with Langmuir−Blodgett Films Terminated by CF₃(CH₂)_n−, n-Perfluoroalkyl, or n-Alkyl Groups

  摘要：

  Langmuir-Blodgett (L-B) films prepared from 18,18,18-trifluorooctadecanoic acid [CF3(CH2)(16)-COOH], perfluorotetradecanoic acid [n-C13F27COOH], or octadecanoic acid [n-C17H35COOH] were used as target surfaces for hyperthermal ion-surface collisions. The synthesis of 18,18,18-trifluorooctadecanoic acid and the preparation of the L-B film from this compound using a subphase containing Al3+ are reported in this paper. The Ion-surface collision results show that the outermost surface group, namely CF3 vs CH3, is the main determinant for the efficiency of both energy transfer and electron transfer during low-energy(e.g., 10-100 eV) polyatomic ion-surface collisions. For atomic projectile ions, there is evidence of penetration into a depth of the films.

  DOI：

  10.1021/ja990719a
• 作为产物：
  描述：

  10-烯酸甲酯 在 chromium(VI) oxide 、 盐酸 、 lithium aluminium tetrahydride 、 Raney Ni (W-2) 、 硫酸 、 氢溴酸 、 lithium 、 溶剂黄146 、 mercury dichloride 、 nickel dichloride 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 甲苯 为溶剂， 反应 73.0h， 生成 18,18,18-trifluorooctadecanoic acid
  参考文献：
  名称：

  Dissociative and Reactive Hyperthermal Ion−Surface Collisions with Langmuir−Blodgett Films Terminated by CF₃(CH₂)_n−, n-Perfluoroalkyl, or n-Alkyl Groups

  摘要：

  Langmuir-Blodgett (L-B) films prepared from 18,18,18-trifluorooctadecanoic acid [CF3(CH2)(16)-COOH], perfluorotetradecanoic acid [n-C13F27COOH], or octadecanoic acid [n-C17H35COOH] were used as target surfaces for hyperthermal ion-surface collisions. The synthesis of 18,18,18-trifluorooctadecanoic acid and the preparation of the L-B film from this compound using a subphase containing Al3+ are reported in this paper. The Ion-surface collision results show that the outermost surface group, namely CF3 vs CH3, is the main determinant for the efficiency of both energy transfer and electron transfer during low-energy(e.g., 10-100 eV) polyatomic ion-surface collisions. For atomic projectile ions, there is evidence of penetration into a depth of the films.

  DOI：

  10.1021/ja990719a

文献信息

• Trifluoromethyl Derivatization of the Ganglioside, GM1
  作者：Krishna Kumar、Zhao Liu

  DOI：10.1055/s-0029-1218777

  日期：2010.6

  A practical synthetic route to a terminally trifluoromethylated analogue of the ganglioside GM1 is described. It is based on regioselective chemical manipulation of naturally occurring GM1 isolated from bovine brain. Lyso-GM1 obtained by simple chemical transformation was then simply acylated with the NHS ester of trifluorostearic acid. The ability to attach fluorinated acyl chains of different lengths to glycosphingolipids is expected to have broad applicability in chemical biology and mass spectral imaging of soft tissue.

  本文介绍了神经节苷脂 GM1 末端三氟甲基化类似物的实用合成路线。它基于对从牛脑中分离出来的天然 GM1 的区域选择性化学处理。通过简单的化学转化获得的溶血-GM1 然后与三氟硬脂酸的 NHS 酯进行简单的酰化。将不同长度的含氟酰基链连接到糖磷脂上的能力有望在化学生物学和软组织质谱成像中得到广泛应用。
• Surfactant compounds and uses thereof
  申请人：——

  公开号：US20040234556A1

  公开（公告）日：2004-11-25

  A pharmaceutical aerosol formulation comprising a particulate medicament, one or more fluorocarbon or hydrogen-containing fluorocarbon propellants and a compound of the general formula (I) or a salt or solvate thereof, wherein A represents a straight chain C 1-16 alkylene substituted by n groups of formula B; n represents an integer 1 to 3; and B independently represents C 1-4 fluoroalkylC 0-6 alkylene-, C 1-4 fluoroalkylC 0-6 alkylene-O—, or C 1-4 alkylC 0-6 alkylene-O— wherein at least one substituent of formula B contains at least one fluorine atom and each C 1-4 fluoroalkyl- moiety contains one or more fluorine atoms but not more than 3 consecutive perfluorinated carbon atoms. The invention also extends to uses of compounds of formula (I) and certain novel compounds within the definition of formula (I). 1

  一种制药气雾剂配方，包括颗粒状药物、一种或多种氟碳或含氢氟碳喷射剂和通式（I）的化合物或其盐或溶剂物，其中A代表被n个B式基团取代的直链C1-16烷基；n代表整数1至3；B独立地表示C1-4氟烷基C0-6烷基、C1-4氟烷基C0-6烷基-O-，或C1-4烷基C0-6烷基-O-，其中式B的至少一个取代基含有至少一个氟原子，每个C1-4氟烷基基团含有一个或多个氟原子，但不超过3个连续的全氟碳原子。本发明还涉及使用式（I）化合物和某些新颖的符合式（I）定义的化合物。
• The Synthesis of ω-Trifluorostearic Acid and ω-Trifluoro-<i>n</i>-octadecyl Amine
  作者：GILBERT. GAVLIN、RICHARD G. MAGUIRE

  DOI：10.1021/jo01118a002

  日期：1956.12.1
• SALTS OF PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1091958A1

  公开（公告）日：2001-04-18
• SURFACTANT COMPOUNDS AND USES THEREOF
  申请人：GLAXO GROUP LIMITED

  公开号：EP1411896B1

  公开（公告）日：2006-03-22