5-甲基-3-(2-甲基丙基)己-2-烯醛 | 585538-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-甲基-3-(2-甲基丙基)己-2-烯醛
• 英文名称: 5-methyl-3-(2-methylpropyl)hex-2-en-1-one
• 英文别名: 3-isobutyl-5-methyl-hex-2-enal；2-Hexenal, 5-methyl-3-(2-methylpropyl)-；5-methyl-3-(2-methylpropyl)hex-2-enal
• CAS: 585538-79-0
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: VVYKCIZLRFPQOK-UHFFFAOYSA-N

物化性质

• 沸点：
  102-103 °C(Press: 14 Torr)
• 密度：
  0.834±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  5-甲基-3-(2-甲基丙基)己-2-烯醛 在 palladium on activated charcoal 咪唑 、 lithium aluminium tetrahydride 、 氢气 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-(2-iodoethyl)-2,6-dimethylheptane
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol (DAG). 25. Exploration of the sn-1 and sn-2 Carbonyl Functionality Reveals the Essential Role of the sn-1 Carbonyl at the Lipid Interface in the Binding of DAG-Lactones to Protein Kinase C

  摘要：

  Diacylglycerol (DAG) lactones with altered functionality (C=O -> CH2 or C=O -> C=S) at the sn-1 and sn-2 carbonyl pharmacophores were synthesized and used as probes to dissect the individual role of each carbonyl in the binding to protein kinase C (PKC). The results suggest that the hydrated sn-1 carbonyl is engaged in very strong hydrogen-bonding interactions with the charged lipid headgroups and organized water molecules at the lipid interface. Conversely, the sn-2 carbonyl has a more modest contribution to the binding process as a result of its involvement with the receptor (Cl domain) via conventional hydrogen bonding to the protein. The parent DAG-lactones, E-6 and Z-7, were designed to bind exclusively in the sn-2 binding mode to ensure the correct orientation and disposition of pharmacophores at the binding site.

  DOI：

  10.1021/jm050352m
• 作为产物：
  描述：

  二异丁基酮 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 5-甲基-3-(2-甲基丙基)己-2-烯醛
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol (DAG). 25. Exploration of the sn-1 and sn-2 Carbonyl Functionality Reveals the Essential Role of the sn-1 Carbonyl at the Lipid Interface in the Binding of DAG-Lactones to Protein Kinase C

  摘要：

  Diacylglycerol (DAG) lactones with altered functionality (C=O -> CH2 or C=O -> C=S) at the sn-1 and sn-2 carbonyl pharmacophores were synthesized and used as probes to dissect the individual role of each carbonyl in the binding to protein kinase C (PKC). The results suggest that the hydrated sn-1 carbonyl is engaged in very strong hydrogen-bonding interactions with the charged lipid headgroups and organized water molecules at the lipid interface. Conversely, the sn-2 carbonyl has a more modest contribution to the binding process as a result of its involvement with the receptor (Cl domain) via conventional hydrogen bonding to the protein. The parent DAG-lactones, E-6 and Z-7, were designed to bind exclusively in the sn-2 binding mode to ensure the correct orientation and disposition of pharmacophores at the binding site.

  DOI：

  10.1021/jm050352m

文献信息

• [EN] PROTEIN KINASE C AGONISTS<br/>[FR] AGONISTES DE PROTÉINE KINASE C
  申请人：GILEAD SCIENCES INC

  公开号：WO2020176505A1

  公开（公告）日：2020-09-03

  The present disclosure relates generally to certain diacylglycerol lactone compounds, pharmaceutical compositions comprising said compounds, and methods of making and using said compounds and pharmaceutical compositions. The compounds and compositions disclosed herein may be used for the treatment or prevention of diseases, disorders, or infections modifiable by protein kinase C (PKC) agonists, such as HIV.

  本公开涉及某些二酰基甘油内酯化合物，包括该化合物的药物组合物，以及制备和使用该化合物和药物组合物的方法。本文所披露的化合物和组合物可用于治疗或预防可通过蛋白激酶C（PKC）激动剂调节的疾病、疾病或感染，如艾滋病。
• Ansell et al., Journal of the Chemical Society, 1956, p. 911,914
  作者：Ansell et al.

  DOI：——

  日期：——
• VERWENDUNG VON HEXENAL-DERIVATEN ALS RIECHSTOFFE
  申请人：KAO CORPORATION

  公开号：EP1476527B1

  公开（公告）日：2007-04-11
• Use of hexenal derivates as perfumes
  申请人：Markert Thomas

  公开号：US20050130875A1

  公开（公告）日：2005-06-16

  The invention relates to hexenal derivatives of general structure (I), in which one of the bonds represented by dashes is a C—C single bond and the other is a C═C double bond, with the proviso that the C═C double bond can have a Z or E configuration, provided that it is in the C¾ position. Said derivatives are characterised by an interesting and original perfume that pervades a wide area and are suitable for use as perfumes, for example in cosmetic preparations, technical products or the alcohol-based perfume industry.
• US7259135B2
  申请人：——

  公开号：US7259135B2

  公开（公告）日：2007-08-21