2-(3,5-dichloro-4'-fluoro<1,1'-biphenyl>-2-yl)-4,5-dihydro-4,4-dimethyloxazole | 78444-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3,5-dichloro-4'-fluoro<1,1'-biphenyl>-2-yl)-4,5-dihydro-4,4-dimethyloxazole
• 英文别名: 2-(3,5-dichloro-4'-fluoro-2-[1,1'-biphenyl]yl)-4,4-dimethyl-2-oxazoline；2-[2,4-dichloro-6-(4-fluorophenyl)phenyl]-4,4-dimethyl-5H-1,3-oxazole
• CAS: 78444-55-0
• 化学式: C₁₇H₁₄Cl₂FNO
• 分子量: 338.209
• InChiKey: WRQRAGZTISDBRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,5-dichloro-4'-fluoro<1,1'-biphenyl>-2-yl)-4,5-dihydro-4,4-dimethyloxazole 生成 2-(3,5-dichloro-4'-fluoro<1,1'-biphenyl>-2-yl)-4,5-dihydro-3,4,4-trimethyloxazolium iodide
  参考文献：
  名称：

  WILLARD, A. K.;NOVELLO, F. C.;HOFFMAN, W. F.;CRAGOE, E. J. ,, JR.

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-dichloro-6-methoxybenzaldehyde 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 41.62h， 生成 2-(3,5-dichloro-4'-fluoro<1,1'-biphenyl>-2-yl)-4,5-dihydro-4,4-dimethyloxazole
  参考文献：
  名称：

  3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 3. 7-(3,5-Disubstituted-[1,1'-biphenyl]-2-yl)-3,5-dihydroxy-6-heptenoic acids and their lactone derivatives

  摘要：

  The syntheses of a series of 7-(3,5-disubstituted [1,1'-bephenyl]-2-yl)-3,5-dihydroxy-6-heptenoic acids and their lactones are reported. Intrinsic 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitory activity is enhanced markedly when the biphenyl moiety is substituted by chloro or methyl groups at positions 3 and 5 and a fluoro group at position 4'. These substitutions, followed by resolution, provided compounds 100(+) and 110(+) with 2.8 times the intrinsic inhibitory activity of compactin. Compound 100(+) was shown to possess the same chirality in the lactone ring as compactin by single-crystal X-ray crystallography.

  DOI：

  10.1021/jm00152a002

文献信息

• Substituted pyranone inhibitors of cholesterol synthesis
  申请人：Merck & Co., Inc.

  公开号：US04710513A1

  公开（公告）日：1987-12-01

  6-Phenyl-, phenylalkyl- and phenylethenyl-4-hydroxytetrahydropyran-2-ones in the 4(R)-trans stereoisomeric forms are potent inhibitors of cholesterol synthesis by virtue of their ability to inhibit the enzyme, 3-hydroxy-3-methylglutaryl-coenzyme A reductase.

  6-苯基、苯基烷基和苯基乙烯基-4-羟基四氢吡喃-2-酮以4(R)-反式异构体形式是胆固醇合成的强效抑制剂，因其能够抑制酶3-羟基-3-甲基戊二酰辅酶A还原酶。
• Cis/trans isomerization of
  申请人：Merck & Co., Inc.

  公开号：US04308378A1

  公开（公告）日：1981-12-29

  Biologically inactive cis-6-(substituted-arylethenyl)-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-on es are isomerized to the corresponding anti-hypercholesterolemic trans-isomers by heating in the presence of a heavy metal salt.

  存在重金属盐的加热条件下，生物学上不活性的顺式-6-(取代芳基乙烯基)-3,4,5,6-四氢-4-羟基-2H-吡喃-2-酮异构化为相应的抗高胆固醇反式异构体。
• Substituted 6-Phenethyl-and phenylethenyl-3,4,5,6-tetrahydro-4-hydroxytetraydropyran-2-ones in the4-R trans stereoisomeric forms and the corresponding dihydroxy acids, process for preparing and pharmaceutical composition comprising them
  申请人：Merck & Co., Inc.

  公开号：EP0024348A1

  公开（公告）日：1981-03-04

  6-Phenyl-, phenalkyl- and phenylethenyl-4-hydroxytetrahydropyran-2-ones in the 4- R trans stereoisomeric forms having the structure wherein A is H or methyl; E is a direct bond, -CH2-, -CH2-CH2-, -CH2-CH2-CH2- or-CH-CH-; and R1, R2 and R3 have several meanings, and the corresponding dihydroxy acids in which the lactone ring is hydrolytically opened, and the pharmaceutically acceptable salts of said dihydroxy acids, and the lower alkyl and the phenyl, dimethylamino or acetylamino-substituted lower alkyl esters of said dihydroxy acids; and processes for preparing them. These compounds are potent inhibitors of cholesterol synthesis by the enzyme hydroxymethyl glutaryl coenzyme A reductase.

  6-苯基、苯基烷基和苯基乙烯基-4-羟基四氢吡喃-2-酮的 4- R 反式立体异构体，其结构为 其中 A 是 H 或甲基 E为直接键、-CH2-、-CH2-CH2-、-CH2-CH2-或-CH-CH-；R1、R2和R3有多种含义，以及相应的内酯环被水解打开的二羟基酸、所述二羟基酸的药学上可接受的盐、所述二羟基酸的低级烷基和苯基、二甲基氨基或乙酰氨基取代的低级烷基酯；以及制备它们的工艺。这些化合物是羟甲基戊二酰辅酶 A 还原酶合成胆固醇的强效抑制剂。
• STOKKER, G. E.
  作者：STOKKER, G. E.

  DOI：——

  日期：——
• WILLARD, A. K.;NOVELLO, F. C.;HOFFMAN, W. F.;CRAGOE, E. J. ,, JR.
  作者：WILLARD, A. K.、NOVELLO, F. C.、HOFFMAN, W. F.、CRAGOE, E. J. ,, JR.

  DOI：——

  日期：——