2-异丙基-2-丙基丙二酸 | 4441-94-5

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-异丙基-2-丙基丙二酸
• 英文名称: 2-isopropyl-2-propylmalonic acid
• 英文别名: 2-Isopropyl-2-propylmalonic acid；2-propan-2-yl-2-propylpropanedioic acid
• CAS: 4441-94-5
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: URFWRISMYMYADO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-异丙基-2-丙基丙二酸 生成 丙戊酸杂质B 2,2-二-正丙基乙酸
  参考文献：
  名称：

  一种2-烷基-2-丙基丙二酸二酯的制备与水解方法

  摘要：

  本发明涉及式Ⅰ所示的2‑烷基‑2‑丙基丙二酸二酯的制备方法：其特征在于丙二酸二酯与1‑氯丙烷，在碱作用下，催化二丙基化制得式Ⅰ所示的2‑烷基‑2‑丙基丙二酸二酯：#imgabs0#R1，R2选自苄基、C1～C5直链烷基或C3～C5支链烷基；R1和R2相同或不同；R3选自甲基、乙基、丙基、丁基或异丙基。2‑烷基‑2‑丙基丙二酸二酯(Ⅰ)水解制得2‑烷基‑2‑丙基丙二酸(Ⅱ)；Ⅱ脱羧制得2‑烷基戊酸(Ⅲ)。Ⅱ经乙醇水溶液或甲醇水溶液重结晶得到二丙基丙二酸(Ⅱa)；Ⅱa脱羧制得丙戊酸，丙戊酸收率大于85.0％(以丙二酸二酯计)，含量大于99.85％(GC)。

  公开号：

  CN117430509A
• 作为产物：
  描述：

  丙基丙二酸二乙酯 在 氢氧化钾 、 sodium hydride 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-异丙基-2-丙基丙二酸
  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

文献信息

• 一种2-烷基-2-丙基丙二酸二酯的制备与水解方法
  申请人：湖南省湘中制药有限公司

  公开号：CN117430509A

  公开（公告）日：2024-01-23

  本发明涉及式Ⅰ所示的2‑烷基‑2‑丙基丙二酸二酯的制备方法：其特征在于丙二酸二酯与1‑氯丙烷，在碱作用下，催化二丙基化制得式Ⅰ所示的2‑烷基‑2‑丙基丙二酸二酯：#imgabs0#R1，R2选自苄基、C1～C5直链烷基或C3～C5支链烷基；R1和R2相同或不同；R3选自甲基、乙基、丙基、丁基或异丙基。2‑烷基‑2‑丙基丙二酸二酯(Ⅰ)水解制得2‑烷基‑2‑丙基丙二酸(Ⅱ)；Ⅱ脱羧制得2‑烷基戊酸(Ⅲ)。Ⅱ经乙醇水溶液或甲醇水溶液重结晶得到二丙基丙二酸(Ⅱa)；Ⅱa脱羧制得丙戊酸，丙戊酸收率大于85.0％(以丙二酸二酯计)，含量大于99.85％(GC)。
• SULFOXIMINE AND SULFODIIMINE MATRIX METALLOPROTEINASE INHIBITORS
  申请人：FLORIDA STATE UNIVERSITY

  公开号：EP0722321A1

  公开（公告）日：1996-07-24
• EP0722321A4
  申请人：——

  公开号：EP0722321A4

  公开（公告）日：1998-04-15
• [EN] SULFOXIMINE AND SULFODIIMINE MATRIX METALLOPROTEINASE INHIBITORS<br/>[FR] SULFOXIMINE ET SULFODIIMINE INHIBITRICES LA METALLOPROTEINASE MATRICE
  申请人：FLORIDA STATE UNIVERSITY

  公开号：WO1995009620A1

  公开（公告）日：1995-04-13

  (EN) Novel sulfoximine and sulfodiimine matrix metalloproteinase inhibitors of formula (I), wherein: R1 is selected from the group consisting of lower-alkyl, hydroxy lower-alkyl, amino lower-alkyl, carbamoyl lower-alkyl, lower-alkyl carbonyl, lower-alkyoxyalkyl, aralkyl and heteroaralkyl; X is NH or O; R2 is selected from the group consisting of hydrogen, lower-alkyl and aralkyl; R3 is selected from the group consisting of hydrogen, lower-alkyl, amino lower-alkyl, guanyl lower-alkyl, aralkyl and heteroaralkyl; and R4 is selected from the group consisting of lower alkyl, aralkyl and -CH(R5)-C(O)NH2, wherein R5 is selected from the group consisting of hydrogen, lower-alkyl, amino lower-alkyl, guanyl lower-alkyl, imidazoylalkyl, hydroxymethyl, 1-hydroxyethyl, mercapto lower-alkyl and methylthio lower-alkyl; useful for modulating physiological functions or treating diseases and disease conditions associated with matrix metalloproteinase modulation.(FR) Nouvelles sulfoximine et sulfodiimine inhibitrices la métalloprotéinase matrice de formule (I), où R1 est sélectionné dans un groupe consistant en: alkyle inférieur, hydroxyalkyle inférieur, aminoalkyle inférieur, alkyle inférieur de carbamoyle, alkyle inférieur de carbonyle, alkyloxyalkyle inférieur, aralkyle et hétéroaralkyle; X est NH ou O; R2 est sélectionné dans un groupe consistant en: hydrogène, alkyle inférieur, aralkyle; R3 est sélectionné dans un groupe consistant en: hydrogène, alkyle inférieur, aminoalkyle inférieur, alkyle inférieur de guanyle, aralkyle et hétéroaralkyle; R4 est sélectionné dans un groupe consistant en: alkyle inférieur, aralkyle, hétéroaralkyle et -CH(R5)-C(O)NH2, où R5 est sélectionné dans un groupe consistant en: alkyle inférieur, aminoalkyle inférieur, alkyle inférieur de guanyle, imidazoylalkyle, hydroxyméthyle, hydroxyéthyle-1, mercaptoalkyle inférieur et méthylthioalkyle inférieur. Ces nouveaux inhibiteurs s'avèrent utiles pour moduler les fonctions physiologiques, et traiter les maladies ou les affections liées à la modulation de la métalloprotéinase matrice.
• Further Branching of Valproate-Related Carboxylic Acids Reduces the Teratogenic Activity, but Not the Anticonvulsant Effect
  作者：Ursula Bojic、Mohamed M. A. Elmazar、Ralf-Siegbert Hauck、Heinz Nau

  DOI：10.1021/tx950216s

  日期：1996.1.1

  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.