4-(6-bromohexyl)phenol | 64431-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(6-bromohexyl)phenol
• 英文别名: 6-(4-hydroxyphenyl)hexyl bromide
• CAS: 64431-79-4
• 化学式: C₁₂H₁₇BrO
• 分子量: 257.17
• InChiKey: YDCHLTHSRJZOLW-UHFFFAOYSA-N

物化性质

• 沸点：
  357.6±25.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(6-bromohexyl)phenol 在 potassium dihydrogenphosphate 、 sodium methylate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.17h， 生成 Methyl 3-cyano-3-hydroxy-4-[6-(4-hydroxyphenyl)hexylsulfanyl]butanoate
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w
• 作为产物：
  描述：

  6-溴-1-(4-甲氧基苯基)己烷-1-酮 在 盐酸 、 水 、 氢溴酸 、 mercury dichloride 、 锌 作用下， 生成 4-(6-bromohexyl)phenol
  参考文献：
  名称：

  Synthesis of 5-(ω-sulfhydrylalkyl)salicylaldehydes as precursors for the preparation of alkanethiol-modified metal salens

  摘要：

  Using multistep syntheses, we obtained two alkanethiol-modified salicylaldehydes, namely 5-(2-sulfhydrylethyl)-salicylaldehyde and 5-(6-sulfhydrylhexyl)salicylaldehyde. These compounds are precursors for the preparation of alkanethiol-substituted metal salens, which can potentially be used to form surface-modified gold electrodes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01178-9

文献信息

• Methylenedioxyphenyl substituted aliphatic diketones
  申请人：Sterling Drug, Inc.

  公开号：US04093736A1

  公开（公告）日：1978-06-06

  Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester.

  芳基取代的二酮和酮酯，可用作抗病毒剂和杀虫剂，通过将芳基烷基或芳基烯基碘化物与适当的二酮或酮酯的金属盐反应制备。
• Aryl substituted diketones
  申请人：Sterling Drug Inc.

  公开号：US04171378A1

  公开（公告）日：1979-10-16

  Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester.

  芳基取代的二酮和酮酯，可作为抗病毒剂和杀虫剂使用，通过将芳基烷基或芳基烯基碘化物与适当的二酮或酮酯的金属盐反应制备而成。
• Ni-Catalyzed Carboxylation of Unactivated Primary Alkyl Bromides and Sulfonates with CO₂
  作者：Yu Liu、Josep Cornella、Ruben Martin

  DOI：10.1021/ja5064586

  日期：2014.8.13

  A Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2 at atmospheric pressure is described. The method is characterized by its mild conditions and remarkably wide scope without the need for air- or moisture-sensitive reagents, which make it a user-friendly and operationally simple protocol en route to carboxylic acids.
• US4171378A
  申请人：——

  公开号：US4171378A

  公开（公告）日：1979-10-16
• ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme
  作者：Andrew D. Gribble、Roland E. Dolle、Antony Shaw、David McNair、Riccardo Novelli、Christine E. Novelli、Brian P. Slingsby、Virendra P. Shah、David Tew、Barbara A. Saxty、Mark Allen、Pieter H. Groot、Nigel Pearce、John Yates

  DOI：10.1021/jm960167w

  日期：1996.1.1

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.