(+)-4-decyloxymandelic acid | 622854-12-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+)-4-decyloxymandelic acid
• 英文别名: (2S)-2-(4-decoxyphenyl)-2-hydroxyacetic acid
• CAS: 622854-12-0
• 化学式: C₁₈H₂₈O₄
• 分子量: 308.418
• InChiKey: XHCNVZLFPCICMI-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-4-decyloxymandelic acid 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 [(4'-decylbiphenoxycarbonyl)phenyl-4-yl]-2-(4-decyloxyphenyl)-2-(tetrahydro-2H-pyran-2-yloxy)acetate
  参考文献：
  名称：

  Synthesis of novel chiral dopants based on optically active p-substituted mandelic acids

  摘要：

  Novel esters of optically active p-substituted mandelic acids (+)-1 and (+)-2 were prepared by a convergent synthetic strategy in high enantiomeric excess (99% ee). The esters (+)-1 and (+)-2 induce helical macrostructures in the mesophases of achiral liquid-crystal materials, although neither exhibits mesorphism on its own. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00576-7
• 作为产物：
  描述：

  氯仿 、 4-癸氧基苯甲醛 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以72%的产率得到(+)-4-decyloxymandelic acid
  参考文献：
  名称：

  Synthesis of novel chiral dopants based on optically active p-substituted mandelic acids

  摘要：

  Novel esters of optically active p-substituted mandelic acids (+)-1 and (+)-2 were prepared by a convergent synthetic strategy in high enantiomeric excess (99% ee). The esters (+)-1 and (+)-2 induce helical macrostructures in the mesophases of achiral liquid-crystal materials, although neither exhibits mesorphism on its own. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00576-7

文献信息

• Synthesis of novel chiral dopants based on optically active p-substituted mandelic acids
  作者：Andreja Lesac、Sanja Narančić、Maja Šepelj、Duncan W. Bruce、Vitomir Šunjić

  DOI：10.1016/s0957-4166(03)00576-7

  日期：2003.9

  Novel esters of optically active p-substituted mandelic acids (+)-1 and (+)-2 were prepared by a convergent synthetic strategy in high enantiomeric excess (99% ee). The esters (+)-1 and (+)-2 induce helical macrostructures in the mesophases of achiral liquid-crystal materials, although neither exhibits mesorphism on its own. (C) 2003 Elsevier Ltd. All rights reserved.