diethyl 2-isobutyl-2-(prop-2-yn-1-yl)malonate | 109367-92-2

• 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: diethyl 2-isobutyl-2-(prop-2-yn-1-yl)malonate
• 英文别名: isobutyl-prop-2-ynyl-malonic acid diethyl ester；Isobutyl-prop-2-inyl-malonsaeure-diaethylester；Diethyl 2-(2-methylpropyl)-2-prop-2-ynylpropanedioate；diethyl 2-(2-methylpropyl)-2-prop-2-ynylpropanedioate
• CAS: 109367-92-2
• 化学式: C₁₄H₂₂O₄
• mdl: MFCD26276049
• 分子量: 254.326
• InChiKey: KFAASTBQGRDMDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 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：

  diethyl 2-isobutyl-2-(prop-2-yn-1-yl)malonate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 生成 Isobutyl-4-yn-valproic acid
  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：

  Natrium-Verbindung des Isobutylmalonsaeure-diaethylester 、 3-溴丙炔 在 乙醇 作用下， 生成 diethyl 2-isobutyl-2-(prop-2-yn-1-yl)malonate
  参考文献：
  名称：

  Zur Kenntnis der Acetylencarbonsäuren. IX. Mitteilung: Die Bildung ungesättigter Lactone aus Alkinsäuren

  摘要：

  DOI：

  10.1002/ardp.19582910505

文献信息

• 1,1,2‐Trifunctionalization of Terminal Alkynes by Radical Addition–Translocation–Cyclization–Trapping for the Construction of Highly Substituted Cyclopentanes
  作者：Youqing Yang、Constantin G. Daniliuc、Armido Studer

  DOI：10.1002/anie.202011785

  日期：2021.1.25

  Radical 1,1,2‐trifunctionalization of terminal alkynes by an addition–translocation–cyclization–trapping sequence using readily available alkynyl triflones as trifluoromethyl radical precursors and trapping reagents is reported. Cascades occur by addition of the trifluoromethyl radical to a terminal alkyne, 1,5‐hydrogen atom transfer, 5‐exo‐cyclization, and subsequent alkynylation to provide (1‐tr

  据报道，使用易于获得的炔基三氟酮作为三氟甲基自由基前体和捕集试剂，通过加成-易位-环化-捕集顺序使末端炔烃具有自由基1,2,3-三官能团。级联反应是通过将三氟甲基基团加到末端炔烃上，进行1,5-氢原子转移，5-外-环化以及随后的炔基化反应来提供的（1-三氟甲基）炔丙基环戊烷。在高温下，以市售过氧化二苯甲酰或α，α'-偶氮二异丁腈为引发剂进行反应，并以高收率提供高度取代的环戊烷。
• 10.1002/anie.202405678
  作者：Zhou, Yulu、Wu, Zhenzhen、Xu, Jinming、Zhang, Zuxiao、Zheng, Hanliang、Zhu, Gangguo

  DOI：10.1002/anie.202405678

  日期：——

  diastereoselective synthesis of quaternary-carbon-containing fluoroalkylcyclobutanes is realized by photocatalytic 4-exo-trig cyclization cascade of thioalkynes or trifluoromethylalkenes. DFT calculations suggest that a fluorine effect, resulting from hyperconjugative π→σ*C-F interactions, accounts for the α-selective radical addition at the sterically hindered alkene carbon, which facilitates the uncommon

  通过硫代炔或三氟甲基烯烃的光催化4-外三环化级联，实现了含季碳的氟烷基环丁烷的区域选择性和非对映选择性合成。 DFT 计算表明，由超共轭 π→σ* CF相互作用产生的氟效应，解释了空间位阻烯烃碳上的 α-选择性自由基加成，这促进了罕见的 4-exo-trig 环闭合。
• Zur Kenntnis der Acetylencarbonsäuren. IX. Mitteilung: Die Bildung ungesättigter Lactone aus Alkinsäuren
  作者：K. E. Schulte、I. Mleinek、K. H. Schär

  DOI：10.1002/ardp.19582910505

  日期：——
• 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.