2-allyl-3,5-bis (benzyloxy)phenol | 1133728-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-allyl-3,5-bis (benzyloxy)phenol
• 英文别名: 3,5-Bis(phenylmethoxy)-2-prop-2-enylphenol
• CAS: 1133728-87-6
• 化学式: C₂₃H₂₂O₃
• 分子量: 346.426
• InChiKey: SWBKPFGMUNGRAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  2-allyl-3,5-bis (benzyloxy)phenol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 生成 (E)-(5-(3-(2,4-bis(benzyloxy)-6-(methoxymethoxy)-phenyl)prop-1-enyl)-1,3-phenylene)bis(oxy)bis(methylene)-dibenzene
  参考文献：
  名称：

  Enantio Selective Synthesis of New Phenylpropanoid: Isolated from Walsura trifoliata

  摘要：

  从传统药用植物Walsura trifoliata的叶中分离出一种含有黄酮-3-醇的新苯丙烷类化合物。该化合物的结构是基于光谱证据[2D NMR，HREIMS]和其替代合成确定的。这种天然产物的合成是从廉价且易得的起始材料邻苯三酚二水合物中实现的。关键反应序列包括Grubbs-II RCM反应，Wittig反应和利用AD-mix α的Sharpless二羟基化反应。

  DOI：

  10.14233/ajchem.2019.22064
• 作为产物：
  描述：

  (((5-(allyloxy)-1,3-phenylene)bis(oxy))bis(methylene))dibenzene 以 丙酮 为溶剂， 190.0~210.0 ℃ 、13.33 Pa 条件下， 反应 1.0h， 以80%的产率得到2-allyl-3,5-bis (benzyloxy)phenol
  参考文献：
  名称：

  Enantio Selective Synthesis of New Phenylpropanoid: Isolated from Walsura trifoliata

  摘要：

  从传统药用植物Walsura trifoliata的叶中分离出一种含有黄酮-3-醇的新苯丙烷类化合物。该化合物的结构是基于光谱证据[2D NMR，HREIMS]和其替代合成确定的。这种天然产物的合成是从廉价且易得的起始材料邻苯三酚二水合物中实现的。关键反应序列包括Grubbs-II RCM反应，Wittig反应和利用AD-mix α的Sharpless二羟基化反应。

  DOI：

  10.14233/ajchem.2019.22064

文献信息

• Total Synthesis of Isosilybin B
  作者：Makoto Inai、Yoshinori Ueno、Hiroto Sagara、Hitoshi Ouchi、Fumihiko Yoshimura、Toshiyuki Kan

  DOI：10.1002/ejoc.202200653

  日期：2022.8.12

  The first total synthesis of isosilybin B is reported. The synthesis of the flavanonol framework of isosilybin B was carried out by oxidation of flavanol. The stereogenic centers of flavanonol was constructed by the modified Julia-Kocienski olefination, Sharpless dihydroxylation, and the acidic cyclization via formation of a quinomethide intermediate.

  首次报道了异水飞蓟宾 B 的全合成。异水飞蓟宾B的黄烷醇骨架的合成是通过黄烷醇的氧化来进行的。黄烷醇的立体中心是通过改进的 Julia-Kocienski 烯化、Sharpless 二羟基化和通过形成醌甲基化物中间体的酸性环化来构建的。
• Formal Synthesis of Teadenols via Palladium-Catalyzed 6-endo Cyclization of an Epoxyphenol
  作者：Mitsuru Kitamura、Hiroki Suetake、Kosuke Hoshino、Yuta Higashijima、Masato Kisanuki、Ryohei Yuasa、Yukihiro Yamaguchi、Takahiro Shimazu、Naoya Koga、Hiro Hamada、Nobuhiro Miyori、Hirokazu Shimooka、Tatsuo Okauchi

  DOI：10.1055/a-1890-8287

  日期：2022.9

  Formal syntheses of teadenols A and B are achieved via a key Pd-catalyzed 6-endo cyclization of a phenol possessing a vinyl ­epoxide moiety. Although 5-exo and 6-endo cyclizations compete during cyclizations of epoxides with a nucleophilic moiety at the 5-position, 6-endo cyclization is realized by using a palladium catalyst.

  茶烯醇 A 和 B 的正式合成是通过具有乙烯基环氧化物部分的苯酚的关键 Pd 催化 6-内环化来实现的。虽然 5-外环化和 6-内环化在环氧化物的环化过程中与 5 位的亲核部分竞争，但 6-内环化是通过使用钯催化剂实现的。
• The scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the synthesis of flavonoids
  作者：Angelo H.L. Machado、Marcio A. de Sousa、Daniela C.S. Patto、Luiz F.S. Azevedo、Fernanda I. Bombonato、Carlos Roque D. Correia

  DOI：10.1016/j.tetlet.2009.01.017

  日期：2009.3

  The scope of the Heck arylation of cyclic and acyclic enol ethers with arenediazonium salts was evaluated. Arylation of 2,3-dihydrofuran yielded 2-aryl-2,5-dihydrofurans as the major adducts (>99:1) except when using n-Bu4NHSO4 as additive or 4-NO2PhN2BF4 as arenediazonium salt. 2,3-Dihydropyran provided mixtures of the three possible isomeric Heck adducts. Arylation of n-butylvinylether with arenediazonium bearing electron-donating groups resulted in substituted acetophenones as almost exclusive products in good overall yields, Substituted 4H-chromenes provided 2-aryl-2H-chromenes in moderate yield when applying the Pd(OAc)(2)/2,6-di-t-butyl-4-methylpyridine catalytic system, which were applied in the synthesis of flavonoids. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and Structure–Activity Relationships of EGCG Analogues, a Recently Identified Hsp90 Inhibitor
  作者：Anuj Khandelwal、Jessica A. Hall、Brian S. J. Blagg

  DOI：10.1021/jo401027r

  日期：2013.8.16

  Epigallocatechin-3-gallate (EGCG), the principal polyphenol isolated from green tea, was recently shown to inhibit Hsp90; however, structure activity relationships for this natural product have not yet been produced. Herein, we report the synthesis and biological evaluation of EGCG analogues to establish structure activity relationships between EGCG and Hsp90. All four rings as well as the linker connecting the C- and the D-rings were systematically investigated, which led to the discovery of compounds that inhibit Hs90 and display improvement in efficacy over EGCG. Antiproliferative activity of all the analogues was determined against MCF-7 and SKBr3 cell lines and Hsp90 inhibitory activity of the four most potent analogues was further evaluated by Western blot analyses and degradation of Hsp90-dependent client proteins. The prenyl-substituted aryl ester of 3,5-dihydroxychroman-3-ol ring system was identified as a novel scaffold that exhibits Hsp90 inhibitory activity.