4-(trans-4-butylcyclohexyl)phenylmethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 1616345-43-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(trans-4-butylcyclohexyl)phenylmethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS: 1616345-43-7
• 化学式: C₃₁H₄₄O₁₀
• 分子量: 576.684
• InChiKey: KMBTTWTZQPXFHQ-ZVNRSXLGSA-N

物化性质

• 熔点：
  126 °C
• 沸点：
  621.3±55.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  4-(trans-4-butylcyclohexyl)phenylmethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 5.0h， 以100%的产率得到4-(trans-4-butylcyclohexyl)phenylmethyl β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of chiral dopants based on carbohydrates

  摘要：

  Chiral dopants based on carbohydrates for nematic liquid crystals were synthesized from D-glucose, and their helical twisting power (HTP) values were evaluated. The chiral dopants induced helices in the host nematic liquid crystals. An acetyl derivative having an ether-type glycosidic linkage between carbohydrate and a mesogenic moiety showed the highest HTP value of 10.4 mu m (1), while an acetyl derivative having an anomeric ester-type linkage did not show any HTP. It was surprising that this molecule had no HTP despite the presence of chirality in the molecule. A relationship between HTP and specific rotation was not observed in this study. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.04.007
• 作为产物：
  描述：

  2,3,4,5-tetra-O-acetyl-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 4-(trans-4-butylcyclohexyl)phenylmethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of chiral dopants based on carbohydrates

  摘要：

  Chiral dopants based on carbohydrates for nematic liquid crystals were synthesized from D-glucose, and their helical twisting power (HTP) values were evaluated. The chiral dopants induced helices in the host nematic liquid crystals. An acetyl derivative having an ether-type glycosidic linkage between carbohydrate and a mesogenic moiety showed the highest HTP value of 10.4 mu m (1), while an acetyl derivative having an anomeric ester-type linkage did not show any HTP. It was surprising that this molecule had no HTP despite the presence of chirality in the molecule. A relationship between HTP and specific rotation was not observed in this study. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.04.007