1-(4-undecyloxybenzoyl)benzotriazole | 666830-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1-(4-undecyloxybenzoyl)benzotriazole
• 英文别名: benzotriazol-1-yl-(4-undecoxyphenyl)methanone
• CAS: 666830-08-6
• 化学式: C₂₄H₃₁N₃O₂
• 分子量: 393.529
• InChiKey: BPOTUVGISCMBKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  29.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  57.01
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-hydroxy-7-octyloxy-fluoren-9-ol 、 1-(4-undecyloxybenzoyl)benzotriazole 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 [(9R)-9-hydroxy-7-octoxy-9H-fluoren-2-yl] 4-undecoxybenzoate
  参考文献：
  名称：

  The influence of alkoxy chain length on the ferroelectric properties of chiral fluorenol liquid crystals

  摘要：

  一系列具有不同烷氧链长度组合的异构手性芴醇介晶已被制备，以检验这些化合物形成的手性SmC*相中极性序起源的模型。结果显示，烷氧侧链的转置对自发电极化Ps的符号没有影响，这与一种模型相矛盾，该模型认为极性序源于反平行氢键二聚体的旋转偏倚，这种偏倚最小化了倾斜SmC*相中的自由体积。

  DOI：

  10.1039/b804673e
• 作为产物：
  描述：

  4-十一氧基苯甲酸 在 吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-(4-undecyloxybenzoyl)benzotriazole
  参考文献：
  名称：

  Directed Metalation Route to Ferroelectric Liquid Crystals with a Chiral Fluorenol Core:  The Effect of Restricted Rotation on Polar Order

  摘要：

  A new series of smectic C* (SmC*) mesogens containing a chiral (R)-2-octyloxy side chain and either a fluorenone (2a-e) or chiral fluorenol (3a-e) core were synthesized using a combined directed ortho metalation-directed remote metalation strategy. The SmC* phase formed by the fluorenol mesogens is more stable and has a wider temperature range than that formed by the fluorenone mesogens, which may be ascribed to intermolecular hydrogen bonding according to variable-temperature FT-IR measurements. The C(11) fluorenol mesogens (R,R)-3d and (S,R)-3d were obtained in diastereomerically pure form and gave reduced polarization (P(o)) values of +106 and +183 nC/cm(2), respectively, at 10 K below the SmA*-SmC* phase transition temperature. The difference in P. values suggests that the chiral fluorenol core contributes to the spontaneous polarization of the SmC* phase. This is ascribed to the bent shape of the fluorenol core, which should restrict its rotation with respect to the side chains in the SmC* phase and favor one orientation of its transverse dipole moment along the polar axis, and to steric coupling of the core to the chiral 2-octyloxy side chain.

  DOI：

  10.1021/ja038920f

文献信息

• Directed <i>ortho</i> and Remote Metalation–Suzuki–Miyaura Cross Coupling Route to Azafluorenol Core Liquid Crystals
  作者：Ping-Shan Lai、Ross D. Jansen-van Vuuren、Robert P. Lemieux、Victor Snieckus

  DOI：10.1021/acs.joc.1c01027

  日期：2021.12.17