1,4:3,6-dianhydro-D-sorbitol-2,5-bis(4-acetoxybenzoate) | 1337985-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 1,4:3,6-dianhydro-D-sorbitol-2,5-bis(4-acetoxybenzoate)
• 英文别名: [(3S,3aR,6R,6aR)-6-(4-acetyloxybenzoyl)oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 4-acetyloxybenzoate
• CAS: 1337985-51-9
• 化学式: C₂₄H₂₂O₁₀
• 分子量: 470.433
• InChiKey: FXWINTKOHKQNIN-CIAFKFPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,4:3,6-dianhydro-D-sorbitol-2,5-bis(4-acetoxybenzoate) 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以87%的产率得到2,5-双缩山梨醇-双-4-羟基苯甲酸酯
  参考文献：
  名称：

  Tuning Helical Twisting Power of Isosorbide-Based Chiral Dopants by Chemical Modifications

  摘要：

  Isosorbide-based chiral dopants (ICD) with various substituent groups were newly synthesized to control their helical twisting powers (HTP). Phase transition behaviors of ICD molecules were first investigated by combined techniques of differential scanning calorimetry, wide-angle X-ray diffraction, and cross-polarized optical microscopy. ICD with n-hexyloxy end groups formed the multiple ordered phases, and those with methoxy or acetoxy end groups exhibited a simple crystal-to-isotropic transition. Energy-minimized chemical conformations of ICD molecules revealed that all the ICDs had twisted conformations and that the extension of the benzoyl ester moiety induced a higher twisted conformation. By varying substitution groups, HTPs of ICDs were controlled from 26.6 to 80.2m-1. Particularly, ICD with an acetoxy end group (ICD-2) showed the largest HTP. It was also realized that by controlling the content of ICD-2 from 3.0 to 4.5mol%, the helical pitch length of cholesteric LC mixture was adjusted to reflect a specific visible light.

  DOI：

  10.1080/15421406.2010.526523
• 作为产物：
  描述：

  对羟基苯甲酸 在 吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 37.0h， 生成 1,4:3,6-dianhydro-D-sorbitol-2,5-bis(4-acetoxybenzoate)
  参考文献：
  名称：

  Tuning Helical Twisting Power of Isosorbide-Based Chiral Dopants by Chemical Modifications

  摘要：

  Isosorbide-based chiral dopants (ICD) with various substituent groups were newly synthesized to control their helical twisting powers (HTP). Phase transition behaviors of ICD molecules were first investigated by combined techniques of differential scanning calorimetry, wide-angle X-ray diffraction, and cross-polarized optical microscopy. ICD with n-hexyloxy end groups formed the multiple ordered phases, and those with methoxy or acetoxy end groups exhibited a simple crystal-to-isotropic transition. Energy-minimized chemical conformations of ICD molecules revealed that all the ICDs had twisted conformations and that the extension of the benzoyl ester moiety induced a higher twisted conformation. By varying substitution groups, HTPs of ICDs were controlled from 26.6 to 80.2m-1. Particularly, ICD with an acetoxy end group (ICD-2) showed the largest HTP. It was also realized that by controlling the content of ICD-2 from 3.0 to 4.5mol%, the helical pitch length of cholesteric LC mixture was adjusted to reflect a specific visible light.

  DOI：

  10.1080/15421406.2010.526523

文献信息

• Bio-based chiral dopants having an isohexide skeleton for cholesteric liquid crystal materials
  作者：Seunghan Shin、Jae Won Seo、Jin Ku Cho、Sangyong Kim、Jaeryung Cha、Myoung Seon Gong

  DOI：10.1039/c2gc16261j

  日期：——

  synthesized from bio-based epimeric isohexides (glucose-derived isosorbide and mannose-derived isomannide) and their phase transition behaviors and abilities for developing cholesteric liquid crystal (CLC) films were examined with a consideration of the core structure. In spite of lower reactivity of the endo hydroxy group of isomannide caused by the steric hindrance and intermolecular hydrogen bonding

  手性掺杂剂是由基于生物的差向异构异己酸酯合成的（葡萄糖-衍生的 异山梨醇 和 甘露糖-衍生的 异甘露糖苷），并考虑了其核心结构，研究了它们的相变行为和形成胆甾型液晶（CLC）膜的能力。尽管其内羟基的反应性较低异甘露糖苷 由位阻和分子间氢键引起的，带有异甘露糖苷核的手性掺杂剂的最终合成产率（IH-2为64.5％，IH-4为65.0％）与带有手性掺杂剂的手性掺杂剂相比没有明显的差异。 异山梨醇（IH-1为68.4％，IH-3为74.0％）。另一方面，在相变行为中，尽管具有相同的取代基，但带有异甘露糖苷核的手性掺杂剂的结晶和熔融温度却低于IH-1，IH-3。手性掺杂剂的螺旋扭转力（HTP）异山梨醇 （IH-1和IH-3）高于手性掺杂剂 异甘露糖苷（IH-2和IH-4）。IH-1和III-3所计算的高毒农药为26.6和42.1微米-1，分别。在IH-3的情况下，可以通过控制CLC的量来调整CLC的螺旋节距长度以反射可见光，并在5