trans-(E)-6-[2-(2,4-dichloro-6-phenylmethoxyphenyl)ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one

• 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: trans-(E)-6-[2-(2,4-dichloro-6-phenylmethoxyphenyl)ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one
• 英文别名: 6-[2-(2-Benzyloxy-4,6-dichloro-phenyl)-vinyl]-4-hydroxy-tetrahydro-pyran-2-one；(4R,6S)-6-[(E)-2-(2,4-dichloro-6-phenylmethoxyphenyl)ethenyl]-4-hydroxyoxan-2-one
• 化学式: C₂₀H₁₈Cl₂O₄
• 分子量: 393.267
• InChiKey: YTUFBVSBCXFOAL-YCZSJOHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-(E)-6-[2-(2,4-dichloro-6-phenylmethoxyphenyl)ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one 在 铑 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到trans-6-[2-(2,4-dichloro-6-phenylmethoxyphenyl)ethyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one
  参考文献：
  名称：

  Substituted pyranone inhibitors of cholesterol synthesis

  摘要：

  4(R)-trans立体异构形式的6-苯基、苯基烷基和苯基乙烯基-4-羟基四氢吡喃-2-酮是胆固醇合成的有效抑制剂，因为它们能够抑制酶3-羟基-3-甲基戊二酰辅酶A还原酶。

  公开号：

  US04459422A1
• 作为产物：
  描述：

  (E)-3-<2,4-dichloro-6-(phenylmethoxy)phenyl>-2-propenal 在 sodium hydroxide 、 sodium tetrahydroborate 、 正丁基锂 、 3 A molecular sieve 、 sodium hydride 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.5h， 生成 trans-(E)-6-[2-(2,4-dichloro-6-phenylmethoxyphenyl)ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one
  参考文献：
  名称：

  3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 2. Structural modification of 7-(substituted aryl)-3,5-dihydroxy-6-heptenoic acids and their lactone derivatives

  摘要：

  A series of 7-(substituted aryl)-3,5-dihydroxy-6-heptenoic (heptanoic) acids and their lactone derivatives have been prepared and tested for inhibition of 3-hydroxy-3-methylglutaryl-coenzyme A reductase in vitro. A systematic exploration of the structure-activity relationships in this series led to the synthesis of (+)-trans-(E)-6-[2-[2,4-dichloro-6-[(4-fluorophenyl) methoxyl]phenyl]ethyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (66(+)), which has one-half of the inhibitory activity of compactin.

  DOI：

  10.1021/jm00152a001

文献信息

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

  公开号：US04375475A1

  公开（公告）日：1983-03-01

  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.

  4(R)-反式立体异构形式的6-苯基、苯基烷基和苯乙烯基-4-羟基四氢吡喃-2-酮是胆固醇合成的有效抑制剂，因为它们能够抑制酶3-羟基-3-甲基戊二酰辅酶A还原酶。
• 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。
• US4375475A
  申请人：——

  公开号：US4375475A

  公开（公告）日：1983-03-01
• US4459422A
  申请人：——

  公开号：US4459422A

  公开（公告）日：1984-07-10
• US4567289A
  申请人：——

  公开号：US4567289A

  公开（公告）日：1986-01-28