13-hydroxy-tridecanenitrile | 22054-11-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 13-hydroxy-tridecanenitrile
• 英文别名: ω-Oxy-n-dodecylcyanid；ω-Oxy-tridecylsaeure-nitril；13-Hydroxy-tridecannitril
• CAS: 22054-11-1
• 化学式: C₁₃H₂₅NO
• 分子量: 211.348
• InChiKey: XNGJZLQIAGINER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  15.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.02
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  13-hydroxy-tridecanenitrile 在 sodium azide 、 potassium carbonate 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 44.0h， 生成 12-(1-benzyl-1H-tetrazol-5-yl)dodecan-1-ol
  参考文献：
  名称：

  Synthesis of [60]fullerene derivatives bearing five-membered heterocyclic wings and an investigation of their photophysical kinetic properties

  摘要：

  The preparation, characterization and photophysical properties of six new stable [6,6]-closed fullerene cycloadducts bearing five-membered heterocycles are described. The modified [60]fullerenes are obtained by a simple and rapid synthesis via a Bingel-type reaction with tetrazole and oxadiazole malonate derivatives. The photophysical kinetics of these new fullerene derivatives in toluene solution under ultraviolet illumination (375 nm, UVA) are studied by electron paramagnetic resonance and free-radical spin-trapping using alpha-phenyl-N-tert-butyl nitrone as a spin-trap. The results are compared with pure [60]fullerene and [6,6]-phenyl C-61 butyric acid methyl ester (C-60-PCBM). It is concluded that for all six new compounds as well as pure [60]fullerene and PCBM both superoxide and singlet oxygen are produced in the first stages of UVA illumination following the type I and II mechanisms, respectively. In all cases singlet oxygen is produced as the primary dominant species; however, the type I mechanism always occurs in parallel with type II. In the end, the superoxide is self-dismuted into hydroxyl radicals, thus yielding PBN-OH center dot spin adducts (g = 2.007 and a(hf) (N-14) = 1.54 mT). The kinetic reaction constants and their efficiencies in the production of reactive oxygen species at 375 nm and per mW of absorbed power are determined. The experimental results are consistent with an autocatalytic reaction model in which the system evolutes under UVA illumination, with superoxide catalyzing the conversion of singlet oxygen into more superoxide. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2010.10.007
• 作为产物：
  描述：

  12-溴-1-十二烷醇 在 potassium cyanide 、 乙醇 作用下， 生成 13-hydroxy-tridecanenitrile
  参考文献：
  名称：

  Chuit et al., Helvetica Chimica Acta, 1927, vol. 10, p. 187

  摘要：

  DOI：

文献信息

• 10.1021/acs.joc.4c01106
  作者：Yan, Yonggang、Wang, Pengpeng、Dong, Jianyang、Li, Gang、Wang, Chao、Xue, Dong

  DOI：10.1021/acs.joc.4c01106

  日期：——

  the predominant method for the synthesis of adiponitrile, which is an important precursor for polymer production. However, the use of fossil-derived alkenes raises environmental concerns, and hydrogen cyanide is highly volatile and extremely toxic. Herein, we report the use of biomass-derived 1,4-butanediol, as well as other primary alcohols, for photochemical synthesis of linear and branched nitriles

  镍催化的 1,3-丁二烯与氰化氢气体的氢氰化是合成己二腈的主要方法，而己二腈是聚合物生产的重要前体。然而，使用化石衍生的烯烃会引起环境问题，而且氰化氢具有高度挥发性和剧毒性。在此，我们报道了使用生物质衍生的 1,4-丁二醇以及其他伯醇，以 1,4-二氰基苯作为 CN 源，进行直链和支链腈和二腈（包括己二腈）的光化学合成。这种温和、可持续的方法不需要氰化氢气体或对空气或湿气敏感的金属催化剂，适用于生产作为二胺前体的二腈，这对于开发新型聚酰胺具有潜在的用途。
• Cottier,L.; Descotes,G., Bulletin de la Societe Chimique de France, 1971, p. 4557 - 4562
  作者：Cottier,L.、Descotes,G.

  DOI：——

  日期：——
• Colonge,J. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1969, vol. 268, p. 1155 - 1156
  作者：Colonge,J. et al.

  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.
• Chuit et al., Helvetica Chimica Acta, 1927, vol. 10, p. 187
  作者：Chuit et al.

  DOI：——

  日期：——