n-butyl 3-n-butyloxy-5-hydroxyphenyl ether | 100964-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: n-butyl 3-n-butyloxy-5-hydroxyphenyl ether
• 英文别名: phloroglucinol dibutyl ether；3,5-dibutoxyphenol；3,5-Dibutoxy-phenol
• CAS: 100964-36-1
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: HDUROKRIYIOGER-UHFFFAOYSA-N

物化性质

• 熔点：
  39-40 °C
• 沸点：
  160-165 °C(Press: 0.10 Torr)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  正溴丁烷 、 n-butyl 3-n-butyloxy-5-hydroxyphenyl ether 在 氢氧化钾 、 MeO(CH₂CH₂O)nMe (M 500) 作用下， 以 水 为溶剂， 反应 1.0h， 以70%的产率得到1,3,5-tributoxybenzene
  参考文献：
  名称：

  Kirillova, K. M.; Skvortsova, T. A.; Nikonova, L. Z., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 3.1, p. 427 - 430

  摘要：

  DOI：
• 作为产物：
  描述：

  正溴丁烷 、 间苯三酚 在 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.1h， 以75%的产率得到n-butyl 3-n-butyloxy-5-hydroxyphenyl ether
  参考文献：
  名称：

  Zinc-catalyzed Williamson ether synthesis in the absence of base

  摘要：

  Zinc powder was found to be a highly efficient catalyst for the synthesis of aromatic ethers using microwave heating in the presence of N,N-dimethylformamide as well as under stirring in an oil-bath using tetrahydrofuran as solvent without any inorganic base. This method can be used for selective mono-, di- or tri-O-alkylations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.009

文献信息

• Synthesis of catechin and epicatechin conjugates
  申请人：Nestec S.A.

  公开号：EP2557079A1

  公开（公告）日：2013-02-13

  The present invention relates generally to catechin and epicatechin conjugates of formula (I). For example, a chemical synthesis process for the preparation of catechin and epi-catechin compounds, in particular of catechin and epi-catechin conjugates is disclosed. A further aspect of the invention pertains to new catechin and epi-catechin conjugate compounds.

  本发明一般涉及公式（I）的儿茶素和表儿茶素共轭物。例如，公开了一种用于制备儿茶素和表儿茶素化合物，特别是儿茶素和表儿茶素共轭物的化学合成过程。该发明的另一个方面涉及新的儿茶素和表儿茶素共轭化合物。
• O-Alkylation of phenol derivatives via a nucleophilic substitution
  作者：Clément Cazorla、Émilie Pfordt、Marie-Christine Duclos、Estelle Métay、Marc Lemaire

  DOI：10.1039/c1gc15481h

  日期：——

  The alkylation of phenol derivatives can be achieved in good yield via Lewis or Brønsted acid. The only by-product of the reaction is water and the catalyst can be recycled when using Brønsted acid.

  这 烷基化 的 苯酚可以通过路易斯酸或布朗斯台德酸以高收率获得衍生物。该反应的唯一副产物是水 和 催化剂 使用布朗斯台德酸可回收利用。
• Peptides capable of inhibiting the activity of HIV protease, their preparation and their therapeutic use
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0587311A1

  公开（公告）日：1994-03-16

  Compounds of formula (I) : [wherein: R¹ is hydrogen, alkyl, aralkyl, -CORa, -CORb, -CSRa, -CSRb, -SO₂Rb, -CONHRb, -CSNHRb, -CONRbRb or -CSNRbRb; R² is hydrogen or alkyl; R³ is hydrogen, alkylidene, substituted alkyl, or Rb; R⁴ is optionally substituted alkyl, cycloalkyl, or aryl; R⁵ is RbO-, RbRbN-, RbHN-, aralkyloxycarbonyloxy or aralkyloxycarbonylamino, or R⁵ is -(CH₂)p-D-(CH₂)r- [where D is a single bond, carbonyl, oxygen, sulphur, -NH-, -(CH₂=CH₂)- or -NHCO-; and p and r are each 0 or an integer from 1 to 5]; A is -(CH₂)m-B-(CH₂)n- [where B is a single bond, carbonyl, oxygen, sulphur, -NH-, -(CH₂=CH₂)- or -NHCO-; and m and n are each 0 or an integer from 1 to 5]; Ra is alkoxy, aralkyloxy, aryloxy or alkoxycarbonyl; Rb is optionally substituted alkyl, cycloalkyl, heterocyclic, aryl or arylalkenyl]; and pharmaceutically acceptable salts and esters thereof and pro-drugs therefor, have the ability to inhibit the activity of HIV protease and may thus be used for the treatment and prophylaxis of AIDS.

  化合物的化学式为(I)：[其中：R¹为氢，烷基，芳基烷基，-CORa，-CORb，-CSRa，-CSRb，-SO₂Rb，-CONHRb，-CSNHRb，-CONRbRb或-CSNRbRb；R²为氢或烷基；R³为氢，烷基亚甲基，取代烷基或Rb；R⁴为可选取代的烷基，环烷基或芳基；R⁵为RbO-，RbRbN-，RbHN-，芳基烷氧羰氧基氧或芳基烷氧羰氨基，或R⁵为-(CH₂)p-D-(CH₂)r- [其中D为单键，酰基，氧，硫，-NH-，-(CH₂=CH₂)-或-NHCO-；p和r分别为0或1到5的整数]；A为-(CH₂)m-B-(CH₂)n- [其中B为单键，酰基，氧，硫，-NH-，-(CH₂=CH₂)-或-NHCO-；m和n分别为0或1到5的整数]；Ra为烷氧基，芳基烷氧基，芳氧基或烷氧羰基；Rb为可选取代的烷基，环烷基，杂环，芳基或芳基烷烯基]；以及其药学上可接受的盐和酯以及其前药，具有抑制HIV蛋白酶活性的能力，因此可用于治疗和预防艾滋病。
• Preparation of (+)-Catechin, (-)-Epicatechin, (-)-Catechin, and (+)-Epicatechin and Their 5,7,3',4'-Tetra-O-Benzyl Analogues
  申请人：Romanczyk, JR. Leo J.

  公开号：US20100048920A1

  公开（公告）日：2010-02-25

  Processes for preparing racemic mixtures of 5,7,3′,4′-tetra-O-benzyl-(±)-catechin and (±)-epicatechin involves (i) condensing 2-hydroxy-4,6-bis(benzyloxy)-acetophenone and 3,4-bis(benzyloxy)benzaldehyde, cyclizing the resulting compound, oxidizing the resulting compound; (ii) dihydroxylating (E)-3-(3′,4′-bis(benzyloxy)phenyl)prop-2-ene-1-ol and reducing the 1,2-diol; or (iii) coupling 3,5-bis(benzyloxy)phenol with (E)-3,5-bis(benzyloxy)-2-(3′,4′-bis(benzyloxy)phenyl)allyl)phenol and cyclizing the resulting chalcone. A process for preparing the benzylated epimers of catechin and epicatechin involves seven steps. 3,4-Bis(benzyloxy)benzaldehyde is coupled with 2-hydroxy-4,6-benzyloxy-acetophenone to form a chalcone. The chalcone is selectively reduced to an alkene. The phenolic group of the alkene is protected. The protected alkene is asymetrically dihydroxylated. The resulting compound is deprotected, cyclized, and finally hydrolyzed. Epimers resulting from these processes are chemically resolved or separated by chiral high pressure liquid chromatography. Also disclosed is a method for preparing enantiomerically pure 5,7,3′,4′-tetra-O-benzyl-(+)-catechin from a racemic mixture using dibenzoyl-L-tartaric acid monomethyl ester. Further, disclosed is an improved process for preparing dibenzoyl-L-tartaric acid monomethyl ester.

  制备5,7,3′,4′-四-O-苄基-(±)-儿茶素和(±)-表儿茶素的外消旋混合物的过程包括：(i)缩合2-羟基-4,6-双(苄氧基)-乙酮和3,4-双(苄氧基)苯甲醛，环化生成化合物，氧化化合物；(ii)双羟基化(E)-3-(3′,4′-双(苄氧基)苯基)丙-2-烯-1-醇，还原1,2-二醇；或(iii)将3,5-双(苄氧基)苯酚与(E)-3,5-双(苄氧基)-2-(3′,4′-双(苄氧基)苯基)丙烯基)苯酚偶联，生成的查尔酮环化。制备儿茶素和表儿茶素的苄基异构体的过程包括七个步骤。3,4-双(苄氧基)苯甲醛与2-羟基-4,6-双(苄氧基)-乙酮偶联形成查尔酮。查尔酮被选择性还原为烯烃。烯烃的酚基被保护。保护的烯烃被不对称地二羟基化。生成的化合物被去保护，环化，最后水解。这些过程生成的异构体通过手性高压液相色谱进行化学分离。还公开了一种使用二苯乙酰-L-酒石酸单甲酯制备对映纯5,7,3′,4′-四-O-苄基-(+)-儿茶素的方法。此外，还公开了一种改进的制备二苯乙酰-L-酒石酸单甲酯的方法。
• Ethers of Phloroglucinol
  作者：Joseph C. Touchstone、James Ashmore、Max N. Huffman

  DOI：10.1021/ja01602a049

  日期：1956.11