isopropyl-propyl-malonic acid diethyl ester | 62391-98-4

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: isopropyl-propyl-malonic acid diethyl ester
• 英文别名: Isopropyl-propyl-malonsaeure-diaethylester；diethyl 2-isopropyl-2-propylmalonate；Diethyl-2-isopropyl-2-propylmalonat；diethyl 2-propan-2-yl-2-propylpropanedioate
• CAS: 62391-98-4
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: OFOXHBRNNXYCMV-UHFFFAOYSA-N

物化性质

• 沸点：
  253.0±8.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isopropyl-propyl-malonic acid diethyl ester 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 生成 丙戊酸杂质B 2,2-二-正丙基乙酸
  参考文献：
  名称：

  Further Branching of Valproate-Related Carboxylic Acids Reduces the Teratogenic Activity, but Not the Anticonvulsant Effect

  摘要：

  In the present study, compounds derived from the anticonvulsant drug valproic acid (VPA, 2-n-propylpentanoic acid) and analogues known to be teratogenic were synthesized with an additional carbon-branching in one of the side chains. The substances were tested for their ability to induce anticonvulsant-activity and sedation in adult mice, and neural tube defects (exencephaly) in the offspring of pregnant animals (Han:NMRI mice). In all cases, the rates of exencephaly, embryolethality, and fetal weight retardation induced by the methyl-branched derivatives were very low when compared to those of the parent compounds, These novel compounds exhibited anticonvulsant activity which was not significantly different from that of VPA. Neurotoxicity was considerably lower for some compounds as compared to VPA. Anticonvulsant activity and neurotoxicity of branched short chain fatty acids are far less structure-dependent and not related to teratogenic potency. Within this series of compounds, (+/-)-4-methyl-2-n-propyl-4-pentenoic acid and (+/-)-2-isobutyl-4-pentenoic acid exhibited the most favorable profile in regard to high anticonvulsant effect, low sedation, and teratogenicity. Valproic acid analogues with additional methyl branching may be valuable antiepileptic agents with low teratogenic potential.

  DOI：

  10.1021/tx950216s
• 作为产物：
  描述：

  丙基丙二酸二乙酯 、 2-溴丙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 isopropyl-propyl-malonic acid diethyl ester
  参考文献：
  名称：

  Further Branching of Valproate-Related Carboxylic Acids Reduces the Teratogenic Activity, but Not the Anticonvulsant Effect

  摘要：

  In the present study, compounds derived from the anticonvulsant drug valproic acid (VPA, 2-n-propylpentanoic acid) and analogues known to be teratogenic were synthesized with an additional carbon-branching in one of the side chains. The substances were tested for their ability to induce anticonvulsant-activity and sedation in adult mice, and neural tube defects (exencephaly) in the offspring of pregnant animals (Han:NMRI mice). In all cases, the rates of exencephaly, embryolethality, and fetal weight retardation induced by the methyl-branched derivatives were very low when compared to those of the parent compounds, These novel compounds exhibited anticonvulsant activity which was not significantly different from that of VPA. Neurotoxicity was considerably lower for some compounds as compared to VPA. Anticonvulsant activity and neurotoxicity of branched short chain fatty acids are far less structure-dependent and not related to teratogenic potency. Within this series of compounds, (+/-)-4-methyl-2-n-propyl-4-pentenoic acid and (+/-)-2-isobutyl-4-pentenoic acid exhibited the most favorable profile in regard to high anticonvulsant effect, low sedation, and teratogenicity. Valproic acid analogues with additional methyl branching may be valuable antiepileptic agents with low teratogenic potential.

  DOI：

  10.1021/tx950216s

文献信息

• Alpha-cyano-phenoxybenzyl-isovalerates
  申请人：Shell Oil Company

  公开号：US04042710A1

  公开（公告）日：1977-08-16

  Compounds of the formula ##STR1## wherein R is alkenyl, aralkyl or alkyl; X is H, CN, thioamide, or alkynyl; and Y is phenoxyphenyl or phthalimido, are useful as pesticides.

  式子为##STR1##的化合物，其中R为烯丙基，芳基烷基或烷基；X为H，CN，硫代酰胺或炔基；Y为苯氧基苯基或邻苯二甲酰亚胺，可用作杀虫剂。
• 2-Substituted isovaleric acid ester pesticides
  申请人：Shell Oil Company

  公开号：US04100363A1

  公开（公告）日：1978-07-11

  Compounds of the formula ##STR1## wherein R is alkenyl, aralkyl or alkyl; X is H, CN, thioamide, or alkynyl; and Y is phenoxyphenyl or phthalimido, are useful as pesticides.

  化合物的公式为##STR1##其中R是烯丙基，芳基甲基或烷基; X是H，CN，硫酰胺或炔基; Y是苯氧苯基或邻苯二甲酰亚胺，可用作杀虫剂。
• Thiobarbiturates. II
  作者：Ellis Miller、James C. Munch、Frank S. Crossley、Walter H. Hartung

  DOI：10.1021/ja01298a007

  日期：1936.7
• US4100363A
  申请人：——

  公开号：US4100363A

  公开（公告）日：1978-07-11