3,8-Diethyl-decane-4,7-dione | 123184-08-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,8-Diethyl-decane-4,7-dione
• 英文别名: 3,8-Diethyldecane-4,7-dione；3,8-diethyldecane-4,7-dione
• CAS: 123184-08-7
• 化学式: C₁₄H₂₆O₂
• 分子量: 226.359
• InChiKey: JVAZLLLBKIBOON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氨基-丙腈富马酸盐(1:1) 、 3,8-Diethyl-decane-4,7-dione 在 对甲苯磺酸 作用下， 以 溶剂黄146 为溶剂， 反应 8.0h， 生成 3-[2,5-Bis-(1-ethyl-propyl)-pyrrol-1-yl]-propionitrile
  参考文献：
  名称：

  Inhibitors of cholesterol biosynthesis. 1. trans-6-(2-Pyrrol-1-ylethyl)-4-hydroxypyran-2-ones, a novel series of HMG-CoA reductase inhibitors. 1. Effects of structural modifications at the 2- and 5-positions of the pyrrole nucleus

  摘要：

  A novel series of trans-6-(2-pyrrol-1-ylethyl)-4-hydroxypyran-2-ones and their dihydroxy acid derivatives were prepared and evaluated for their ability to inhibit the enzyme HMG-CoA reductase in vitro. A systematic study of substitution at the 2- and 5-positions of the pyrrole ring revealed that optimum potency was realized with the 2-(4-fluorophenyl)-5-isopropyl derivative 8x, which possessed 30% of the in vitro activity of the potent fungal metabolite compactin (I). A molecular modeling analysis led to the description of a pharmacophore model characterized by (A) length limits of 5.9 and 3.3 A for the 2- and 5-substituents, respectively, as well as an overall width limit of 10.6 A across the pyrrole ring from the 2- to the 5-substituent and (B) an orientation of the ethyl(ene) bridge to the 4-hydroxypyran-2-one ring nearly perpendicular to the planes of the parent pyrrole, hexahydronaphthalene, and phenyl rings of the structures examined (Figure 3, theta = 80-110 degrees). Attempts to more closely mimic compactin's polar isobutyric ester side chain with the synthesis of 2-phenylpyrroles containing polar phenyl substituents resulted in analogues with equal or slightly reduced potencies when compared to the 2-[(unsubstituted or 4-fluoro)phenyl]pyrroles, supporting the hypothesis that inhibitory potency is relatively insensitive to side-chain polarity or charge distribution in this area.

  DOI：

  10.1021/jm00163a005
• 作为产物：
  描述：

  2-乙基丁醛 、 4-乙基己-1-烯-3-酮 在 2-(2-hydroxyethyl)-3-methyl-4-benzylthiazolium chloride 、 三乙胺 作用下， 反应 12.0h， 以53%的产率得到3,8-Diethyl-decane-4,7-dione
  参考文献：
  名称：

  Inhibitors of cholesterol biosynthesis. 1. trans-6-(2-Pyrrol-1-ylethyl)-4-hydroxypyran-2-ones, a novel series of HMG-CoA reductase inhibitors. 1. Effects of structural modifications at the 2- and 5-positions of the pyrrole nucleus

  摘要：

  A novel series of trans-6-(2-pyrrol-1-ylethyl)-4-hydroxypyran-2-ones and their dihydroxy acid derivatives were prepared and evaluated for their ability to inhibit the enzyme HMG-CoA reductase in vitro. A systematic study of substitution at the 2- and 5-positions of the pyrrole ring revealed that optimum potency was realized with the 2-(4-fluorophenyl)-5-isopropyl derivative 8x, which possessed 30% of the in vitro activity of the potent fungal metabolite compactin (I). A molecular modeling analysis led to the description of a pharmacophore model characterized by (A) length limits of 5.9 and 3.3 A for the 2- and 5-substituents, respectively, as well as an overall width limit of 10.6 A across the pyrrole ring from the 2- to the 5-substituent and (B) an orientation of the ethyl(ene) bridge to the 4-hydroxypyran-2-one ring nearly perpendicular to the planes of the parent pyrrole, hexahydronaphthalene, and phenyl rings of the structures examined (Figure 3, theta = 80-110 degrees). Attempts to more closely mimic compactin's polar isobutyric ester side chain with the synthesis of 2-phenylpyrroles containing polar phenyl substituents resulted in analogues with equal or slightly reduced potencies when compared to the 2-[(unsubstituted or 4-fluoro)phenyl]pyrroles, supporting the hypothesis that inhibitory potency is relatively insensitive to side-chain polarity or charge distribution in this area.

  DOI：

  10.1021/jm00163a005

文献信息

• RECOVERY OF BIS(DIARYLPHENOL) LIGANDS DURING THE PRODUCTION OF ISOPULEGOL
  申请人：Heydrich Gunnar

  公开号：US20100010253A1

  公开（公告）日：2010-01-14

  The present invention relates to a method of working up an aluminium-containing reaction product from the production of isopulegol by cyclization of citronellal in the presence of complex compounds, comprising at least one ligand of the formula (I), where Ar 1 , Ar 2 , Ar 3 , Ar 4 are chosen from C 6 -C 15 -aryl or C 2 -C 15 -hetero; R 1 , R 2 , R 3 , R 4 are chosen from H, C 1 -C 6 -alkyl, C 1 -C 6 -perfluoroalkyl, C 1 -C 6 -alkoxy, C 7 -C 12 -aralkyl, halogen, SiR 5b R 6b R 7b , C 6 -C 10 -aryl, NR 8b R 9b , SR 10b , NO 2 ; and where R 1 or R 2 and/or R 3 or R 4 , together with A, can form an aromatic or nonaromatic cycle; etc.; in which a) the aluminum-containing reaction product is subjected to distillative separation, b) the isopulegol-depleted bottom product is brought into close contact with an aqueous base and c) the ligand of the formula (I) is separated off from the organic phase, preferably by crystallization. Moreover, the invention relates to a method of producing isopulegol, and to a method of producing menthol.

  本发明涉及一种从在复合物存在下环化香茅醛制备异莪醇的反应产物中处理含铝反应产物的方法，所述复合物至少包括式(I)的配体，其中Ar1、Ar2、Ar3、Ar4选自C6-C15芳基或C2-C15杂环基；R1、R2、R3、R4选自H、C1-C6烷基、C1-C6全氟烷基、C1-C6烷氧基、C7-C12芳基烷基、卤素、SiR5bR6bR7b、C6-C10芳基、NR8bR9b、SR10b、NO2；其中R1或R2和/或R3或R4与A一起可以形成芳香环或非芳香环等；其中a）含铝反应产物经过蒸馏分离，b）异莪醇去除底部产物与水性碱物质密切接触，c）式(I)的配体从有机相中分离出来，优选通过结晶分离。此外，本发明还涉及一种生产异莪醇的方法和一种生产薄荷醇的方法。
• DIARYLPHENOXY-ALUMINIUM-VERBINDUNGEN
  申请人：BASF SE

  公开号：EP1858903B1

  公开（公告）日：2008-10-08
• US8134034B2
  申请人：——

  公开号：US8134034B2

  公开（公告）日：2012-03-13