4-acetoxy-3,5-di-t-butyl-2-(2-methyl-2-propenyl)phenol | 173662-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-acetoxy-3,5-di-t-butyl-2-(2-methyl-2-propenyl)phenol
• 英文别名: [2,6-ditert-butyl-4-hydroxy-3-(2-methylprop-2-enyl)phenyl] acetate
• CAS: 173662-54-9
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: SPKKOVBESTYAOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-acetoxy-3,5-di-t-butyl-2-(2-methyl-2-propenyl)phenol 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以1.19 g的产率得到5-acetoxy-4,6-di-tert-butyl-2,3-dihydro-2,2-dimethylbenzofuran
  参考文献：
  名称：

  Design and Synthesis of 4,6-Di-tert-butyl-2,3-dihydro-5-benzofuranols as a Novel Series of Antiatherogenic Antioxidants

  摘要：

  Antioxidants have been considered as potential antiatherogenic agents by inhibiting oxidation of low-density lipoprotein (LDL), albeit vitamin E, a natural antioxidant, has failed to show reduction on atherosclerosis in clinical trials. We have rationally designed and synthesized a novel series of antioxidants, 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols, to overcome the clinical limitation of vitamin E. In vitro, the compounds showed a potent inhibitory effect on lipid peroxidation detected as 2-methyl-6-(p-methoxyphenyl)-3,7-dihydroimidazo[1,2-a]pyrazin3-one (MCLA)-dependent chemiluminescence in linoleic acid autoxidation. They also inhibited the LDL oxidation induced by Cu2+, and the inhibition is more potent than that of vitamin E and probucol. In vivo, 4,6-di-tert-butyl-2,3-dihydro-2,2-dipentyl-5-benzofuranoI (BO-653, 1f), an optimal compound, showed the highest concentration in plasma and LDL fraction in Watanabe heritable hyperlipidemic rabbits, due to its high affinity to LDL. The isolated LDL samples from the If-treated rabbits showed potent resistibility to LDL oxidation. Compound If has been taken into clinical trials.

  DOI：

  10.1021/jm030062a
• 作为产物：
  描述：

  4-acetoxy-3,5-di-tert-butylphenol 在 sodium hydride 、 N,N-二甲基苯胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 38.5h， 生成 4-acetoxy-3,5-di-t-butyl-2-(2-methyl-2-propenyl)phenol
  参考文献：
  名称：

  Design and Synthesis of 4,6-Di-tert-butyl-2,3-dihydro-5-benzofuranols as a Novel Series of Antiatherogenic Antioxidants

  摘要：

  Antioxidants have been considered as potential antiatherogenic agents by inhibiting oxidation of low-density lipoprotein (LDL), albeit vitamin E, a natural antioxidant, has failed to show reduction on atherosclerosis in clinical trials. We have rationally designed and synthesized a novel series of antioxidants, 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols, to overcome the clinical limitation of vitamin E. In vitro, the compounds showed a potent inhibitory effect on lipid peroxidation detected as 2-methyl-6-(p-methoxyphenyl)-3,7-dihydroimidazo[1,2-a]pyrazin3-one (MCLA)-dependent chemiluminescence in linoleic acid autoxidation. They also inhibited the LDL oxidation induced by Cu2+, and the inhibition is more potent than that of vitamin E and probucol. In vivo, 4,6-di-tert-butyl-2,3-dihydro-2,2-dipentyl-5-benzofuranoI (BO-653, 1f), an optimal compound, showed the highest concentration in plasma and LDL fraction in Watanabe heritable hyperlipidemic rabbits, due to its high affinity to LDL. The isolated LDL samples from the If-treated rabbits showed potent resistibility to LDL oxidation. Compound If has been taken into clinical trials.

  DOI：

  10.1021/jm030062a

文献信息

• Therapeutic agents for renal diseases and organ preservatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US06133279A1

  公开（公告）日：2000-10-17

  Herein disclosed are therapeutic agents for renal diseases and organ preservatives containing a compound represented by the general formula (1): ##STR1## wherein X represents an oxygen atom or a group represented by the general formula (2): ##STR2## where n represents an integer from 0 to 2, R.sub.1 represents a hydrogen atom or an acyl group, R.sub.2 represents a hydrogen atom, a lower alkyl group or a lower alkenyl group, R.sub.3 represents a lower alkyl group, R.sub.4, R.sub.5 and R.sub.6, which may be the same or different, each represents a hydrogen atom or an optionally substituted alkyl group, and R.sub.6 further represents a formyl, carboxyl, lower alkoxycarbonyl or optionally substituted carbamoyl group, or R.sub.3 and R.sub.4 may be taken together to form a five-membered ring, or R.sub.5 and R.sub.6 may be taken together to form a cycloalkyl group, provided that when the five-membered ring formed by R.sub.3 and R.sub.4 and the benzene ring form benzofuran or benzo[b]thiophene, R.sub.6 is absent.

  本文披露了一种用于肾脏疾病的治疗剂和含有一种由一般式（1）表示的化合物的器官保护剂：##STR1## 其中X表示氧原子或由一般式（2）表示的基团：##STR2## 其中n表示0到2的整数，R.sub.1表示氢原子或酰基基团，R.sub.2表示氢原子、低级烷基基团或低级烯基基团，R.sub.3表示低级烷基基团，R.sub.4，R.sub.5和R.sub.6，可以相同也可以不同，每个表示氢原子或可选取代的烷基基团，R.sub.6还表示甲酰基、羧基、低级烷氧羰基或可选取代的氨基羰基，或R.sub.3和R.sub.4可以结合形成五元环，或R.sub.5和R.sub.6可以结合形成环烷基基团，但当R.sub.3和R.sub.4形成的五元环和苯环形成苯并呋喃或苯并噻吩时，R.sub.6不存在。
• 4,6 Di-t-butyl-5-hydroxy-2,3-dihydrobenzothiophene
  申请人：Chugai Seiyak Kabushiki Kaisha

  公开号：US05789436A1

  公开（公告）日：1998-08-04

  A compound represented by formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom, a lower alkyl group or an acyl group; R.sub.2 and R.sub.3, which may be the same or different, each represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted alkenyl group; R.sub.4 represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted alkenyl group, or R.sub.4 forms a double bond between the carbon atom to which R.sub.3 is bonded and the adjacent carbon atom to form a benzothiophene skeleton, or R.sub.3 and R.sub.4 are taken together to form a 5- to 8-membered spiro ring which may contain a hetero atom, e.g., oxygen, sulfur or nitrogen; and n represents an integer of 0 to 2, or a pharmaceutically acceptable salt thereof. The compound of formula (I) exhibits an inhibitory action on the oxidative modification of LDL and is useful as therapeutics of arteriosclerosis.

  化合物的化学式为(I): ##STR1## 其中R.sub.1代表氢原子，低级烷基或酰基；R.sub.2和R.sub.3，可以相同也可以不同，分别代表氢原子、可选取代的烷基或可选取代的烯基；R.sub.4代表氢原子、可选取代的烷基或可选取代的烯基，或R.sub.4与R.sub.3结合形成双键，形成苯并噻吩骨架，或R.sub.3和R.sub.4结合形成5-8成员的螺环，其中可以含有杂原子，例如氧、硫或氮；n代表0到2的整数，或其药学上可接受的盐。化合物(I)表现出对LDL氧化修饰的抑制作用，可用作动脉硬化的治疗药物。
• Intimal thickening inhibitory agent
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US06440999B1

  公开（公告）日：2002-08-27

  An intimal thickening inhibitory agent comprising, as an active ingredient, a compound represented by formula (1): wherein x represents an oxygen atom or a group of formula (2) —S—(O)n  (2) wherein n represents an integer of from 0 to 2, R1 represents a hydrogen atom or an acyl group; R2 represents a hydrogen atom, a lower alkyl group or a lower alkenyl group; R3 represents a lower alkyl group; and R4, R5, and R6, which may be the same or different, each represent a hydrogen atom or a substituted or unsubstituted alkyl group; or R3 and R4 may be taken together to form a 5-membered ring; or R5 and R6 may be taken together to form a cycloalkyl group; provided that R6 is nil when R3 and R4 are taken together to form benzofuran or benzo[b]thiophene.

  一种内膜增厚抑制剂，其作为活性成分包括由式（1）表示的化合物： 其中，x代表氧原子或式（2）中的基团-S-(O)n (2)，其中n代表0至2的整数，R1代表氢原子或酰基；R2代表氢原子、较低的烷基或较低的烯基；R3代表较低的烷基；而R4、R5和R6，它们可能相同也可能不同，每个代表氢原子或取代或未取代的烷基；或R3和R4可以结合成为5-成员环；或R5和R6可以结合成为环烷基；其中，当R3和R4结合成苯并呋喃或苯并噻吩时，R6为零。
• 4,6-DI-t-BUTYL-2,3-DIHYDROBENZOTHIOPHENES WHICH INHIBIT LDL OXIDATION
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP0791589A1

  公开（公告）日：1997-08-27

  A compound represented by formula (I): wherein R1 represents a hydrogen atom, a lower alkyl group or an acyl group; R2 and R3, which may be the same or different, each represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted alkenyl group; R4 represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted alkenyl group, or R4 forms a double bond between the carbon atom to which R3 is bonded and the adjacent carbon atom to form a benzothiophene skeleton, or R3 and R4 are taken together to form a 5- to 8-membered spiro ring which may contain a hetero atom, e.g., oxygen, sulfur or nitrogen; and n represents an integer of 0 to 2, or a pharmaceutically acceptable salt thereof. The compound of formula (I) exhibits an inhibitory action on the oxidative modification of LDL and is useful as therapeutics of arteriosclerosis.

  由式(I)代表的化合物： 其中 R1 代表氢原子、低级烷基或酰基；R2 和 R3 可以相同或不同，各自代表氢原子、任选取代的烷基或任选取代的烯基；R4 代表氢原子、任选取代的烷基或任选取代的烯基，或 R4 在与 R3 键合的碳原子和相邻碳原子之间形成双键以形成苯并噻吩骨架，或 R3 和 R4 合在一起形成 5 至 8 元螺环，该螺环可包含杂原子，例如g.,氧、硫或氮；以及 n 代表 0 至 2 的整数、 或其药学上可接受的盐。式（I）化合物对低密度脂蛋白的氧化修饰具有抑制作用，可作为动脉硬化的治疗药物。
• INTIMAL THICKENING INHIBITOR
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0868913A1

  公开（公告）日：1998-10-07

  An intimal thickening inhibitory agent comprising, as an active ingredient, a compound represented by formula (1): wherein X represents an oxygen atom or a group of formula (2): wherein n represents an integer of from 0 to 2, R1 represents a hydrogen atom or an acyl group; R2 represents a hydrogen atom, a lower alkyl group or a lower alkenyl group; R3 represents a lower alkyl group; and R4, R5, and R6, which may be the same or different, each represent a hydrogen atom or a substituted or unsubstituted alkyl group; or R3 and R4 may be taken together to form a 5-membered ring; or R5 and R6 may be taken together to form a cycloalkyl group; provided that R6 is nil when R3 and R4 are taken together to form benzofuran or benzo[b]thiophene.

  一种内膜增厚抑制剂，其活性成分包括由式（1）代表的化合物： 其中 X 代表氧原子或式（2）的基团： 其中 n 代表 0 至 2 的整数、 R1 代表氢原子或酰基； R2 代表氢原子、低级烷基或低级烯基； R3 代表低级烷基； R4、R5 和 R6 可以相同或不同，各自代表氢原子或取代或未取代的烷基；或 R3 和 R4 组合在一起形成五元环；或 R5 和 R6 组合在一起形成环烷基；但当 R3 和 R4 组合在一起形成苯并呋喃或苯并[b]噻吩时，R6 为零。