(+)-4-benzyloxymandelic acid | 197437-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+)-4-benzyloxymandelic acid
• 英文别名: (S)-4-benzyloxymandelic acid；(2S)-2-hydroxy-2-(4-phenylmethoxyphenyl)acetic acid
• CAS: 197437-40-4
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: ONUIVMPUJMCSLI-AWEZNQCLSA-N

物化性质

• 沸点：
  470.6±40.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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-benzyloxymandelic 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 dodecyl-2-(4-benzyloxyphenyl)-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：

  4-苄氧基苯甲醛 、 氯仿 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以72%的产率得到(+)-4-benzyloxymandelic 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

• Phenylethanolaminotetralincarboxamide derivatives
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：US06046192A1

  公开（公告）日：2000-04-04

  The present invention relates to a phenylethanolaminotetralincarboxamide derivative represented by the general formula: ##STR1## (wherein A represents a lower alkylene group; B represents an amino group, a di(lower alkyl)amino group or a 3 to 7-membered alicyclic amino group which may contain an oxygen atom in the ring; the carbon atom marked with * represents a carbon atom in (R) configuration, (S) configuration or a mixture thereof; and the carbon atom marked with (S) represents a carbon atom in (S) configuration) and a pharmaceutically acceptable salt thereof, which have a selective .beta..sub.2 -adrenergic receptor stimulating effect with relieved burdens on the heart such as tachycardia and are useful as an agent for the prevention of threatened abortion and premature labor, a bronchodilator, and an agent for pain remission and promoting stone removal in urolithiasis.

  本发明涉及一种由通式表示的苯乙醇胺四环羧酰胺衍生物：##STR1##（其中A代表较低的烷基烃基；B代表氨基、二（较低烷基）氨基或3至7成员脂环氨基，该脂环氨基可能在环中含有一个氧原子；用*标记的碳原子代表（R）构型、（S）构型或它们的混合物中的碳原子；用（S）标记的碳原子代表（S）构型中的碳原子），以及其药学上可接受的盐，具有选择性β2-肾上腺素受体刺激作用，减轻心脏负担，如心动过速，并可用作预防威胁性流产和早产的药剂、支气管扩张剂，以及用于疼痛缓解和促进尿路结石排出的药剂。
• PHENYLETHANOLAMINOTETRALINCARBOXAMIDE DERIVATIVES
  申请人：Kissei Pharmaceutical Co. Ltd.

  公开号：EP0893432A1

  公开（公告）日：1999-01-27

  The present invention relates to a phenylethanolaminotetralincarboxamide derivative represented by the general formula: (wherein A represents a lower alkylene group; B represents an amino group, a di(lower alkyl)amino group or a 3 to 7-membered alicyclic amino group which may contain an oxygen atom in the ring; the carbon atom marked with * represents a carbon atom in (R) configuration, (S) configuration or a mixture thereof; and the carbon atom marked with (S) represents a carbon atom in (S) configuration) and a pharmaceutically acceptable salt thereof, which have a selective β2-adrenergic receptor stimulating effect with relieved burdens on the heart such as tachycardia and are useful as an agent for the prevention of threatened abortion and premature labor, a bronchodilator, and an agent for pain remission and promoting stone removal in urolithiasis.

  本发明涉及一种由通式表示的苯乙醇胺四氢甲酰胺衍生物： (其中 A 代表低级亚烷基；B 代表氨基、二(低级烷基)氨基或环中可能含有氧原子的 3 至 7 元脂环氨基；标有 * 的碳原子代表(R)构型、(S)构型或其混合物中的碳原子；标记为(S)的碳原子代表(S)构型的碳原子）及其药学上可接受的盐，它们具有选择性β2-肾上腺素能受体刺激作用，可减轻心动过速等心脏负担，可用作预防妊娠流产和早产的药物、支气管扩张剂、缓解疼痛的药物以及促进泌尿系统结石清除的药物。
• JPS5470231A
  申请人：——

  公开号：JPS5470231A

  公开（公告）日：1979-06-05
• US6046192A
  申请人：——

  公开号：US6046192A

  公开（公告）日：2000-04-04
• 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.