(R)-2-hydroxy-7-(1-methylheptyloxy)fluoren-9-one | 666830-05-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (R)-2-hydroxy-7-(1-methylheptyloxy)fluoren-9-one
• 英文别名: 2-hydroxy-7-[(2R)-octan-2-yl]oxyfluoren-9-one
• CAS: 666830-05-3
• 化学式: C₂₁H₂₄O₃
• 分子量: 324.42
• InChiKey: FIFZTLOOMVVJKX-CQSZACIVSA-N

物化性质

• 熔点：
  88-89 °C
• 沸点：
  493.9±28.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-hydroxy-7-(1-methylheptyloxy)fluoren-9-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.08h， 生成 (RS)-((4-dodecyloxybenzoyl)oxy)-7-((R)-1-methylheptyloxy)fluoren-9-ol
  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
• 作为产物：
  描述：

  (R)-N,N-diethyl 4'-hydroxy-4-(1-methylheptyloxy)biphenyl-2-carboxamide 在 盐酸 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 为溶剂， 反应 20.0h， 生成 (R)-2-hydroxy-7-(1-methylheptyloxy)fluoren-9-one
  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