2-Ethyl-3-hydroxypentanoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Ethyl-3-hydroxypentanoic acid
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: DFUMJYAZRYDCNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Ethyl-3-hydroxypentanoic acid 在 氢氧化钾 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (E)-2-ethylpent-2-enoic acid
  参考文献：
  名称：

  Structure-Activity Relationships of Unsaturated Analogs of Valproic Acid

  摘要：

  The principal metabolite of valproic acid (VPA), 2-ene VPA, appears to share most of VPA's pharmacological and therapeutic properties while lacking its hepatotoxicity and teratogenicity, thus making it a useful lead compound for the development of safer antiepileptic drugs. Analogues of 2-ene VPA were evaluated for anticonvulsant activity in mice using the subcutaneous pentylenetetrazole test. Cyclooctylideneacetic acid exhibited a potency markedly exceeding that of VPA itself with only modest levels of sedation. Potency, as either ED(50) or brain concentration, was highly correlated (r > 0.85) with volume and lipophilicity rather than with one of the shape parameters calculated by molecular modeling techniques, arguing against the existence of a specific receptor site. Instead, a role for the plasma membrane in mediating the anticonvulsant effect is suggested.

  DOI：

  10.1021/jm00017a024
• 作为产物：
  描述：

  (+/-)-erythro-3-(3-hydroxy-2-ethyl-1-oxopentyl)-4-(1-methylethyl)-2-oxazolidinone 在 lithium hydroxide 、 3,4-dibutyl-4-hydroxytoluene 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-Ethyl-3-hydroxypentanoic acid
  参考文献：
  名称：

  Structure-Activity Relationships of Unsaturated Analogs of Valproic Acid

  摘要：

  The principal metabolite of valproic acid (VPA), 2-ene VPA, appears to share most of VPA's pharmacological and therapeutic properties while lacking its hepatotoxicity and teratogenicity, thus making it a useful lead compound for the development of safer antiepileptic drugs. Analogues of 2-ene VPA were evaluated for anticonvulsant activity in mice using the subcutaneous pentylenetetrazole test. Cyclooctylideneacetic acid exhibited a potency markedly exceeding that of VPA itself with only modest levels of sedation. Potency, as either ED(50) or brain concentration, was highly correlated (r > 0.85) with volume and lipophilicity rather than with one of the shape parameters calculated by molecular modeling techniques, arguing against the existence of a specific receptor site. Instead, a role for the plasma membrane in mediating the anticonvulsant effect is suggested.

  DOI：

  10.1021/jm00017a024

文献信息

• Asymmetric reduction of 1,1,1-trifluoroacetone
  申请人：Doswald Stephan

  公开号：US20070009999A1

  公开（公告）日：2007-01-11

  The invention relates to a scalable biocatalytic process for the preparation of S-1,1,1,-trifluoro-2-propanol with a enantiomeric excess of >99% by asymmetric microbial reduction of 1,1,1 -trifluoroacetone with Baker's yeast.

  本发明涉及一种可扩展的生物催化过程，用于通过使用贝克酵母对1,1,1-三氟丙酮进行不对称微生物还原，制备具有大于99％对映体过量的S-1,1,1-三氟-2-丙醇。
• Black, T. Howard; Fields, John D., Synthetic Communications, 1988, vol. 18, # 2, p. 125 - 130
  作者：Black, T. Howard、Fields, John D.

  DOI：——

  日期：——
• Taste improving composition
  申请人：Givaudan Nederland Services B.V.

  公开号：EP1854782B1

  公开（公告）日：2009-09-30
• BLACK, T. HOWARD;FIELDS, JOHN D., SYNTH. COMMUN., 18,(1988) N 2, 125-130
  作者：BLACK, T. HOWARD、FIELDS, JOHN D.

  DOI：——

  日期：——
• ASYMMETRIC REDUCTION OF 1,1,1-TRIFLUOROACETONE
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1904640B1

  公开（公告）日：2009-08-19