12,12,12-trifluoro-1-dodecanol | 20208-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12,12,12-trifluoro-1-dodecanol
• 英文别名: 12,12,12-trifluorododecan-1-ol
• CAS: 20208-17-7
• 化学式: C₁₂H₂₃F₃O
• 分子量: 240.309
• InChiKey: CEOPJYKIBUIKCK-UHFFFAOYSA-N

物化性质

• 沸点：
  259.2±35.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12,12,12-trifluoro-1-dodecanol 在 chromium(VI) oxide 、 盐酸 、 sodium hydroxide 、 硫酸 、 氢溴酸 、 lithium 、 溶剂黄146 、 mercury dichloride 、 锌 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 39.0h， 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：

  12,12,12-三氟十二烷酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以99%的产率得到12,12,12-trifluoro-1-dodecanol
  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

• Rhodium-Catalyzed β-Dehydroborylation of Silyl Enol Ethers: Access to Highly Functionalized Enolates
  作者：Jie Li、Pei Zhao、Ruoling Li、Wen Yang、Wanxiang Zhao

  DOI：10.1021/acs.orglett.1c03796

  日期：2021.12.17

  efficient rhodium-catalyzed β-dehydroborylation of aldehyde-derived silyl enol ethers (SEEs) with bis(pinacolato)diboron (B2pin2) is disclosed. The borylation reactions proceeded well with alkyl- and aryl-substituted SEEs, affording a wide array of valuable functionalized β-boryl silyl enolates with high efficiency and excellent stereoselectivity. Moreover, the borylated products, through versatile

  公开了醛衍生的甲硅烷基烯醇醚(SEE)与双(频哪醇)二硼(B 2 pin 2 )的有效铑催化的β-脱硼氢化。硼基化反应与烷基和芳基取代的 SEE 进行得很好，提供了一系列有价值的功能化 β-硼基甲硅烷基烯醇化物，具有高效率和优异的立体选择性。此外，borylated产品，通过通用的碳-硼键的变换，被容易地转化为合成多样有用分子，包括α羟基酮，官能看到，和宝石-difunctionalized醛。
• Leaving Group Assisted Strategy for Photoinduced Fluoroalkylations Using <i>N</i> -Hydroxybenzimidoyl Chloride Esters
  作者：Weigang Zhang、Zhenlei Zou、Yuanheng Wang、Yi Wang、Yong Liang、Zhengguang Wu、Youxuan Zheng、Yi Pan

  DOI：10.1002/anie.201812192

  日期：2019.1.8

  (RAEs) as alkyl radical precursors have been extensively developed for C−C bond formations. However, the analogous transformations of fluoroalkyl radicals from the corresponding acid or ester precursors remain challenging because of the high oxidation potential of the fluoroalkyl carboxylate anions. The newly developed N‐hydroxybenzimidoylchloride (NHBC) ester provides a general leaving group assisted

  作为烷基自由基前体的氧化还原活性酯（RAE）已广泛开发用于C-C键的形成。然而，由于氟代烷基羧酸根阴离子的高氧化潜力，从相应的酸或酯前体的氟代烷基自由基的类似转化仍然具有挑战性。新开发的N-羟基苯甲酰亚胺基氯（NHBC）酯提供了一般的离去基团辅助策略来生成氟烷基自由基组合，并且可以成功地用于光诱导的脱羧氢氟烷基化反应和未活化烯烃的杂芳基化反应。此外，DFT计算表明，NHBC酯是通过碳氟自由基途径进行的，而其他众所周知的RAE则是通过氮自由基途径进行的。
• Csuk, Rene; Tamba, Maria Gabriela; Kluge, Ralph, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2011, vol. 66, # 10, p. 1069 - 1075
  作者：Csuk, Rene、Tamba, Maria Gabriela、Kluge, Ralph

  DOI：——

  日期：——
• Source of Image Contrast in STM Images of Functionalized Alkanes on Graphite:  A Systematic Functional Group Approach
  作者：Christopher L. Claypool、Francesco Faglioni、William A. Goddard、Harry B. Gray、Nathan S. Lewis、R. A. Marcus

  DOI：10.1021/jp9701799

  日期：1997.7.1

  A series of functionalized alkanes and/or alkyl alcohols have been prepared and imaged by scanning tunneling microscopy (STM) methods on graphite surfaces. The stability of these ordered overlayers has facilitated reproducible collection of STM images at room temperature with submolecular resolution, in most cases allowing identification of individual hydrogen atoms in the alkane chains, but in all cases allowing identification of molecular length features and other aspects of the image that can be unequivocally related to the presence of functional groups in the various molecules of concern. Functional groups imaged in this study include halides (X = F, Cl, Br, I), amines, alcohols, nitriles, alkenes, alkynes, ethers, thioethers, and disulfides. Except for -Cl and -OH, all of the other functional groups could be distinguished from each other and from -Cl or -OH through an analysis of their STM metrics and image contrast behavior. The dominance of molecular topography in producing the STM images of alkanes and alkanols was established experimentally and also was consistent with quantum chemistry calculations. Unlike the contrast of the methylene regions of the alkyl chains, the STM contrast produced by the various functional groups was not dominated by topographic effects, indicating that variations in local electronic coupling were important in producing the observed STM images of these regions of the molecules. For molecules in which electronic effects overwhelmed topographic effects in determining the image contrast, a simple model is presented to explain the variation in the electronic coupling component that produces the contrast between the various functional groups observed in the STM images. Additionally, the bias dependence of these STM images has been investigated and the contrast vs bias behavior is related to factors involving electron transfer and hole transfer that have been identified as potentially being important in dominating the electronic coupling in molecular electron transfer processes.
• ANDRIEU, ANNIE HUGUETTE;BLANCOU, HUBERT;COMMEYRAS, AUGUSTE
  作者：ANDRIEU, ANNIE HUGUETTE、BLANCOU, HUBERT、COMMEYRAS, AUGUSTE

  DOI：——

  日期：——