2,3-dihydro-5-hydroxy-4,6-di-tert-butyl-2,2-dipentylbenzofuran | 157360-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,3-dihydro-5-hydroxy-4,6-di-tert-butyl-2,2-dipentylbenzofuran
• 英文别名: 2,3-dihydro-5-hydroxy-2,2-dipentyl-4,6-di-tert-butylbenzofuran；BO-653；4,6-di-tert-butyl-2,2-di-n-pentyl-5-hydroxy-2,3-dihydrobenzofuran；4,6-di-tert-butyl-2,2-dipentyl-2,3-dihydro-5-benzofuranol；4,6-di-t-butyl-2,2-di-n-pentyl-5-hydroxy-2,3-dihydrobenzofuran；4,6-di-t-butyl-5-hydroxy-2,2-di-n-pentyl-2,3-dihydrobenzofuran；4,6-di-tert-butyl-5-hydroxy-2,2-dipentyl-2,3-dihydrobenzofuran；4,6-ditert-butyl-2,2-dipentyl-3H-1-benzofuran-5-ol
• CAS: 157360-23-1
• 化学式: C₂₆H₄₄O₂
• 分子量: 388.634
• InChiKey: AGURKSYKTJQPNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-5-hydroxy-4,6-di-tert-butyl-2,2-dipentylbenzofuran 、 水 在 甲烷磺酸 二氯甲烷 、 Brine 、 magnesium sulfate 、 silica gel 、 正己烷 作用下， 以 二氯甲烷 为溶剂， 以to give 0.19 g of 6-t-butyl-5-hydroxy-2,2-di-n-pentyl-2,3-dihydrobenzofuran as a colorless oil (yield 22%)的产率得到6-t-butyl-2,2-di-n-pentyl-5-hydroxy-2,3-dihydrobenzofuran
  参考文献：
  名称：

  2,3-dihydrobenzofuran derivatives

  摘要：

  通式（1）中的2,3-二氢苯并呋喃衍生物：其中R1代表氢原子或酰基；R2、R3和R4代表氢原子、低级烷基或低级烯基；R5和R6代表氢原子或可选取代的烷基，或R5和R6结合形成一个环烷基或饱和含氧或烷基取代的氮原子的杂环基，但R2和R3不能同时代表叔丁基，或其光学异构体或药学上可接受的盐可用作治疗或预防各种肾脏疾病和器官保护剂。

  公开号：

  US06403639B1
• 作为产物：
  描述：

  2,6-二叔丁基-4-甲氧基苯酚 在 lithium aluminium tetrahydride 、 碘代三甲硅烷 、 (CH₂)6N₄ 、 硫酸 、 三氟化硼乙醚 、 magnesium 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 113.5h， 生成 2,3-dihydro-5-hydroxy-4,6-di-tert-butyl-2,2-dipentylbenzofuran
  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

• Stability and Reactivity of Aryloxyl Radicals Derived from a Novel Antioxidant BO-653 and Related Compounds. Effects of Substituent and Side Chain in Solution and Membranes
  作者：Akira Watanabe、Noriko Noguchi、Akio Fujisawa、Tatsuhiko Kodama、Kunio Tamura、Osamu Cynshi、Etsuo Niki

  DOI：10.1021/ja9942080

  日期：2000.6.1

  antioxidant, the effects of substituents and side chains on the stability and reactivity of the BO-653 derived radical were studied and compared with the aryloxyl radicals derived from related compounds including α-tocopherol. The rate constants for the reactions of the aryloxyl radicals with themselves, lipid, hydroperoxide, and ascorbate were measured with a stopped-flow electron spin resonance (ESR)

  2,3-Dihydro-5-hydroxy-2,2-dipentyl-4,6-di-tert-butylbenzofuran (BO-653) 是一种新型抗氧化剂，旨在用作抑制体内脂质过氧化的药物。为了了解 BO-653 作为抗氧化剂的作用动力学，我们研究了取代基和侧链对 BO-653 衍生自由基的稳定性和反应性的影响，并与衍生自相关化合物（包括 α-生育酚）的芳氧基自由基进行了比较。芳氧基自由基与自身、脂质、氢过氧化物和抗坏血酸盐反应的速率常数用配备快速混合装置的停流电子自旋共振 (ESR) 光谱仪测量。邻位取代基对双分子衰变反应的速率和与抗坏血酸的反应产生深远的影响，而对与亚油酸甲酯和叔丁基过氧化氢反应的影响要小得多。2-位侧链在有机溶液中没有发挥任何作用，但两个戊基侧链，...
• Process for preparation of a benzofuran derivative
  申请人：——

  公开号：US20030204100A1

  公开（公告）日：2003-10-30

  An industrially useful process for producing benzofuran derivatives of formula (1) 1 by formylating a compound of formula (2) 2 (where A 1 is a protective group), followed by reaction with a compound of formula (4) 3 (where X 1 is a halogen atom), then performing a cyclizing reaction and subsequently performing a reaction for hydroxyl group deprotection.

  一种用于生产苯并呋喃衍生物的工业上有用的过程，首先通过对式(2)的化合物进行甲酰化（其中A1是保护基），然后与式(4)的化合物（其中X1是卤素原子）发生反应，随后进行环化反应，最后进行羟基去保护的反应。
• A new strategy for the synthesis of 4,6-di-tert-butyl-2,2-dipentyl-2,3-dihydro-5-benzofuranol (BO-653), a potent antiatherogenic antioxidant
  作者：Masatoshi Murakata、Masahiro Kimura

  DOI：10.1016/j.tetlet.2010.07.035

  日期：2010.9

  An efficient alternative route to 4,6-di-tert-butyl-2,2-dipentyl-2,3-dihydro-5-benzofuranol (BO-653), a potent antiatherogenic antioxidant, has been developed by the application of the base-promoted dienone-phenol rearrangement reaction. A decisive effect of MgBr2 in the reaction of Grignard reagents is also described.

  通过使用该碱，已开发出一种有效的替代方法，可替代4,6-二叔丁基-2,2-二戊基-2,3-二氢-5-苯并呋喃醇（ BO-653）。 -促进的二烯酮-苯酚重排反应。还描述了MgBr 2在格氏试剂反应中的决定性作用。
• COMPOUNDS AND METHODS FOR TREATING INSULIN RESISTANCE SYNDROME
  申请人：Cohen Stephen Michael

  公开号：US20140227289A1

  公开（公告）日：2014-08-14

  The present invention relates to a method of treating or preventing insulin resistance syndrome in an animal body by administering an inhibitor of protein kinase RNA-like endoplasmic reticulum kinase (PERK) gene, or a functional variant thereof, or an inhibitor of PERK protein or a functional variant thereof or a method of reducing activity of transcription factors of the FOXO family (Foxo 1, 3a, 4 and 6) by administering an inhibitor of protein kinase RNA-like endoplasmic reticulum kinase (PERK) gene, or a functional variant thereof, or an inhibitor of PERK protein or a functional variant thereof. The present invention also relates to different compounds and methods for using PERK gene or PERK protein.

  本发明涉及通过给动物体内注射蛋白激酶RNA样内质网激酶（PERK）基因的抑制剂或其功能变体，或PERK蛋白或其功能变体的抑制剂，或通过给动物体内注射蛋白激酶RNA样内质网激酶（PERK）基因的抑制剂或其功能变体，或PERK蛋白或其功能变体的抑制剂来减少FOXO家族转录因子（Foxo 1、3a、4和6）活性的方法，用于治疗或预防动物体内的胰岛素抵抗综合征。本发明还涉及不同的化合物和使用PERK基因或PERK蛋白的方法。
• 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。