4-acetoxy-3,5-di-tert-butyl-2-formylmethylanisole | 157360-68-4

• 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-tert-butyl-2-formylmethylanisole
• 英文别名: [2,6-ditert-butyl-4-methoxy-3-(2-oxoethyl)phenyl] acetate
• CAS: 157360-68-4
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: CTTWYJVOGXJMFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-acetoxy-3,5-di-tert-butyl-2-formylmethylanisole 在 lithium aluminium tetrahydride 、 碘代三甲硅烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 4,6-di-tert-butyl-5-benzofuranol
  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：

  2,6-二叔丁基-4-甲氧基苯酚 在 sodium periodate 、 四氧化锇 、 碘代三甲硅烷 、 硫酸 、 potassium carbonate 、 N,N-二甲基苯胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 164.0h， 生成 4-acetoxy-3,5-di-tert-butyl-2-formylmethylanisole
  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

• 4,6-Di-t-butyl-dihydrobenzofuran-5-ol and its derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US05574178A1

  公开（公告）日：1996-11-12

  Compounds represented by the general formula as well as intermediates for the synthesis of thereof: ##STR1## where R.sup.1 is a hydrogen atom or an acyl group; R.sup.2 is a lower alkyl group; R.sup.3 is a hydrogen atom or a lower alkyl group; R.sup.4, R.sup.5 and R.sup.6, which may be the same or different, are a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl or aryl group; R.sup.2 and R.sup.4, when taken together, may form a 5-membered ring; R.sup.5 and R.sup.6, when taken together, may form a cycloalkyl group or a heterocyclic group in which at least one methylene on the ring of a cycloalkyl group is substituted by an oxygen atom, a sulfur atom or an alkyl-substituted nitrogen atom, provided that R.sup.6 is not present if the ring formed by R.sup.2 and R.sup.4 taken together is a benzofuran ring. The compounds represented by the general formula (I) have a highly selective anti-oxidative activity and are useful as therapeutics of ischemic diseases such as arteriosclerosis and myocardial infarction.

  通式表示的化合物以及其合成的中间体：##STR1##其中R.sup.1是氢原子或酰基；R.sup.2是较低的烷基；R.sup.3是氢原子或较低的烷基；R.sup.4、R.sup.5和R.sup.6，可以相同也可以不同，是氢原子或可选择取代的烷基、烯基、炔基或芳基；当R.sup.2和R.sup.4一起时，可以形成一个5-成员环；当R.sup.5和R.sup.6一起时，可以形成一个环烷基或一个杂环基，其中环烷基的环上至少有一个甲基被氧原子、硫原子或烷基取代的氮原子取代，前提是如果由R.sup.2和R.sup.4一起形成的环是苯并呋喃环，则R.sup.6不存在。通式（I）表示的化合物具有高度选择性的抗氧化活性，并且可用作治疗缺血性疾病，如动脉粥样硬化和心肌梗死的药物。
• 4-alkoxy-2, 6-di-t-butylphenol derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US05606089A1

  公开（公告）日：1997-02-25

  Compounds represented by the general formula (I), as well as intermediates for the synthesis of thereof: ##STR1## where R.sup.1 is a hydrogen atom or an acyl group; R.sup.2 is a lower alkyl group; R.sup.3 is a hydrogen atom or a lower alkyl group; R.sup.4, R.sup.5 and R.sup.6, which may be the same or different, are a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl or aryl group; R.sup.2 and R.sup.4, when taken together, may form a 5-membered ring; R.sup.5 and R.sup.6, when taken together, may form a cycloalkyl group or a heterocyclic group in which at least one methylene on the ring of a cycloalkyl group is substituted by an oxygen atom, a sulfur atom or an alkyl-substituted nitrogen atom, provided that R.sup.6 is not present if the ring formed by R.sup.2 and R.sup.4 taken together is a benzofuran ring. The compounds represented by the general formula (I) have a highly selective anti-oxidative activity and are useful as therapeutics of ischemic diseases such as arteriosclerosis and myocardial infarction.

  通式（I）所代表的化合物以及其合成中间体： 其中，R.sup.1是氢原子或酰基基团；R.sup.2是较低的烷基基团；R.sup.3是氢原子或较低的烷基基团；R.sup.4，R.sup.5和R.sup.6，可以相同也可以不同，是氢原子或可选取代的烷基，烯基，炔基或芳基基团；当R.sup.2和R.sup.4结合在一起时，可以形成一个5元环；当R.sup.5和R.sup.6结合在一起时，可以形成一个环烷基或杂环基，在环烷基上至少有一个亚甲基被氧原子，硫原子或烷基取代的氮原子所取代，但是当R.sup.2和R.sup.4结合在一起形成苯并呋喃环时，R.sup.6不存在。通式（I）所代表的化合物具有高度选择性的抗氧化活性，可用作缺血性疾病如动脉硬化和心肌梗塞的治疗剂。
• 4-ALKOXY-2,6-DI-t-BUTYLPHENOL DERIVATIVE
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0665208B1

  公开（公告）日：1999-01-13
• US5574178A
  申请人：——

  公开号：US5574178A

  公开（公告）日：1996-11-12
• US5606089A
  申请人：——

  公开号：US5606089A

  公开（公告）日：1997-02-25