4-methyl-3-(isopropyl)-pent-2-enoic acid chloride | 106329-08-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 4-methyl-3-(isopropyl)-pent-2-enoic acid chloride
• 英文别名: 4-Methyl-3-propan-2-ylpent-2-enoyl chloride
• CAS: 106329-08-2
• 化学式: C₉H₁₅ClO
• 分子量: 174.671
• InChiKey: SWCUAKXUENKDFL-UHFFFAOYSA-N

物化性质

• 沸点：
  214.1±9.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methyl-3-(isopropyl)-pent-2-enoic acid chloride 在 吡啶 、 4-二甲氨基吡啶 、 三氯化硼 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.5h， 生成 3-Isopropyl-4-methyl-pent-2-enoic acid (S)-3-hydroxy-2-(3-isopropyl-4-methyl-pentanoyloxy)-propyl ester
  参考文献：
  名称：

  An Optimized Protein Kinase C Activating Diacylglycerol Combining High Binding Affinity (K_i) with Reduced Lipophilicity (log P)

  摘要：

  A small, focused combinatorial library encompassing all possible permutations of acyl branched alkyl chains-small and large, saturated and unsaturated-was generated from the active diacylglycerol enantiomer (S-DAG) to help identify the analogue with the highest binding affinity (lowest K-i) for protein kinase C (PK-C) combined with the minimum lipophilicity (log P). The selected ligand (3B) activated PK-C more effectively than sn-1,2-dioctanoylglycerol (diC8) despite being 1.4 log units more hydrophilic. Compound 3B indeed represents the most potent, hydrophilic DAG ligand to date. With the help of a green fluorescent protein (GFP)tagged PK-C alpha, 3B was able to translocate the full length protein to the membrane with an optimal dose of 100 muM in CHO-K1 cells, while diC8 failed to achieve translocation even at doses 3-fold higher. Molecular modeling of 3B into an empty C1b domain of PK-C delta clearly showed the existence of a preferred binding orientation. In addition, molecular dynamic simulations suggest that binding discrimination could result from a favorable van der Waals (VDW) interaction between the large, branched sn-1 acyl group of 3B and the aromatic rings of Trp252 (PK-C delta) or Tyr252 (PK-C alpha). The DAG analogue of 3B in which the acyl groups are reversed (2C) showed a decrease in binding affinity reflecting the capacity of PK-C to effectively discriminate between alternative orientations of the acyl chains.

  DOI：

  10.1021/jm010052e
• 作为产物：
  描述：

  3-isopropyl-4-methyl-2-pentenoic acid ethyl ester 在 氢氧化钾 、 氯化亚砜 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 4-methyl-3-(isopropyl)-pent-2-enoic acid chloride
  参考文献：
  名称：

  模具气相1-氟丁醚-1-异丁烯基-和2-甲基苯基-炔基-酮。Eine合成冯·埃诺霉素B †

  摘要：

  1-异丁烯基炔基和2-甲基苯基炔基酮的气流热解。甲基霉素B的合成

  DOI：

  10.1002/hlca.19860690306

文献信息

• Die Gasphasen-Flussthermolyse von 1-Isobutenyl- und 2-Methylphenyl-alkinyl-ketonen. Eine Synthese von Methylenomycin B
  作者：Manuel Koller、Martin Karpf、Andr� S. Dreiding

  DOI：10.1002/hlca.19860690306

  日期：1986.5.7

  The Gas-Flow Thermolysis of 1-Isobutenyl Alkynyl and 2-Methylphenyl Alkynyl Ketones. Synthesis of Methylenomycin B

  1-异丁烯基炔基和2-甲基苯基炔基酮的气流热解。甲基霉素B的合成
• An Optimized Protein Kinase C Activating Diacylglycerol Combining High Binding Affinity (<i>K</i>_i) with Reduced Lipophilicity (log P)
  作者：Kassoum Nacro、Dina M. Sigano、Shunqi Yan、Marc C. Nicklaus、Larry L. Pearce、Nancy E. Lewin、Susan H. Garfield、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm010052e

  日期：2001.6.1

  A small, focused combinatorial library encompassing all possible permutations of acyl branched alkyl chains-small and large, saturated and unsaturated-was generated from the active diacylglycerol enantiomer (S-DAG) to help identify the analogue with the highest binding affinity (lowest K-i) for protein kinase C (PK-C) combined with the minimum lipophilicity (log P). The selected ligand (3B) activated PK-C more effectively than sn-1,2-dioctanoylglycerol (diC8) despite being 1.4 log units more hydrophilic. Compound 3B indeed represents the most potent, hydrophilic DAG ligand to date. With the help of a green fluorescent protein (GFP)tagged PK-C alpha, 3B was able to translocate the full length protein to the membrane with an optimal dose of 100 muM in CHO-K1 cells, while diC8 failed to achieve translocation even at doses 3-fold higher. Molecular modeling of 3B into an empty C1b domain of PK-C delta clearly showed the existence of a preferred binding orientation. In addition, molecular dynamic simulations suggest that binding discrimination could result from a favorable van der Waals (VDW) interaction between the large, branched sn-1 acyl group of 3B and the aromatic rings of Trp252 (PK-C delta) or Tyr252 (PK-C alpha). The DAG analogue of 3B in which the acyl groups are reversed (2C) showed a decrease in binding affinity reflecting the capacity of PK-C to effectively discriminate between alternative orientations of the acyl chains.