(R)-7-(1-methylheptyloxy)-2-((4-undecyloxybenzoyl)oxy)fluoren-9-one | 666829-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (R)-7-(1-methylheptyloxy)-2-((4-undecyloxybenzoyl)oxy)fluoren-9-one
• 英文别名: [7-[(2R)-octan-2-yl]oxy-9-oxofluoren-2-yl] 4-undecoxybenzoate
• CAS: 666829-88-5
• 化学式: C₃₉H₅₀O₅
• 分子量: 598.823
• InChiKey: VWCMDENDSYONKV-GDLZYMKVSA-N

物化性质

• 沸点：
  717.0±55.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  44
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-7-(1-methylheptyloxy)-2-((4-undecyloxybenzoyl)oxy)fluoren-9-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.08h， 生成 (R)-7-((R)-1-methylheptyloxy)-2-((4-undecyloxybenzoyl)oxy)fluoren-9-ol 、 (S)-7-((R)-1-methylheptyloxy)-2-((4-undecyloxybenzoyl)oxy)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：

  (S)-(+)-2-辛醇 在 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 偶氮二甲酸二异丙酯 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 异丙醇 为溶剂， 反应 28.83h， 生成 (R)-7-(1-methylheptyloxy)-2-((4-undecyloxybenzoyl)oxy)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

文献信息

• Directed Metalation Route to Ferroelectric Liquid Crystals with a Chiral Fluorenol Core:  The Effect of Restricted Rotation on Polar Order
  作者：J. Adam McCubbin、Xia Tong、Ruiyao Wang、Yue Zhao、Victor Snieckus、Robert P. Lemieux

  DOI：10.1021/ja038920f

  日期：2004.2.1

  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.