ethyl (E)-3-[3,5-bis(phenylmethoxy)phenyl]prop-2-enoate | 937175-36-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (E)-3-[3,5-bis(phenylmethoxy)phenyl]prop-2-enoate
• CAS: 937175-36-5
• 化学式: C₂₅H₂₄O₄
• 分子量: 388.463
• InChiKey: AMCFJKSYJNFJIF-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-[3,5-bis(phenylmethoxy)phenyl]prop-2-enoate 在 甲基磺酰胺 、 K2 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 甲苯 、 叔丁醇 为溶剂， 反应 72.0h， 以83%的产率得到ethyl (2S,3R)-3-[3,5-bis(phenylmethoxy)phenyl]-2,3-dihydroxypropanoate
  参考文献：
  名称：

  Asymmetric Synthesis of a Series of Chiral AB₂ Monomers for Dendrimer Construction

  摘要：

  Efficient preparation of a series of four chiral, nonracemic AB(2) monomers suitable for the construction of dendrimers is presented. Monomers 1-4 possess the common structural features of a diphenolic moiety and a benzylic or aliphatic hydroxyl which render these molecules suitable for convergent dendrimer synthesis. The same basic, high-yielding, five-step sequence is employed for 1-4. Stilbene derivatives 13 and 14 are prepared by a Horner-Wadsworth-Emmons modified Wittig reaction between 3,5- or 3,4-bis(benzyloxy)benzaldehyde (8 and 10) and an ester-substituted benzylphosphonate (11 or 12). Cinnamate derivatives 21 and 22 are prepared similarly from 8 and 10 and triethyl phosphonoacetate. Chirality is introduced in the form of a 1,2-diol unit by Sharpless asymmetric dihydroxylation (AD) (>97% ee in all cases), Protection of the 1,2-diols as their acetonide derivatives provides dioxolane intermediates 17, 18, 25, and 26. Reduction of the ester groups followed by hydrogenolysis of the benzyl ethers yields AB(2) monomers 1-4 in 57-67% overall yield from 8 and 10.

  DOI：

  10.1021/jo961587w
• 作为产物：
  描述：

  3,5-二苄氧基苯甲醇 在 Celite 、 sodium 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 ethyl (E)-3-[3,5-bis(phenylmethoxy)phenyl]prop-2-enoate
  参考文献：
  名称：

  Asymmetric Synthesis of a Series of Chiral AB₂ Monomers for Dendrimer Construction

  摘要：

  Efficient preparation of a series of four chiral, nonracemic AB(2) monomers suitable for the construction of dendrimers is presented. Monomers 1-4 possess the common structural features of a diphenolic moiety and a benzylic or aliphatic hydroxyl which render these molecules suitable for convergent dendrimer synthesis. The same basic, high-yielding, five-step sequence is employed for 1-4. Stilbene derivatives 13 and 14 are prepared by a Horner-Wadsworth-Emmons modified Wittig reaction between 3,5- or 3,4-bis(benzyloxy)benzaldehyde (8 and 10) and an ester-substituted benzylphosphonate (11 or 12). Cinnamate derivatives 21 and 22 are prepared similarly from 8 and 10 and triethyl phosphonoacetate. Chirality is introduced in the form of a 1,2-diol unit by Sharpless asymmetric dihydroxylation (AD) (>97% ee in all cases), Protection of the 1,2-diols as their acetonide derivatives provides dioxolane intermediates 17, 18, 25, and 26. Reduction of the ester groups followed by hydrogenolysis of the benzyl ethers yields AB(2) monomers 1-4 in 57-67% overall yield from 8 and 10.

  DOI：

  10.1021/jo961587w

文献信息

• Synthesis of Catechins via Thiourea/AuCl₃-Catalyzed Cycloalkylation of Aryl Epoxides
  作者：Yongxiang Liu、Xiben Li、Guang Lin、Zheng Xiang、Jing Xiang、Mingzhe Zhao、Jiahua Chen、Zhen Yang

  DOI：10.1021/jo8005649

  日期：2008.6.1

  A diversity-oriented approach for the synthesis of structurally diverse catechins was achieved in good yields via thiourea/AuCl3/AgOTf-catalyzed annulations of aryl epoxides under mild conditions. This new protocol provides a highly efficient entry to a library of catechins-derived natural products, notably anti-HIV agent 8-C-ascorbyl-(−)-epigallocatechin.

  在温和条件下，通过硫脲/ AuCl 3 / AgOTf催化的芳基环氧化物环化反应，以高收率实现了面向结构多样的儿茶素合成的面向多样性的方法。该新协议可高效地访问儿茶素类天然产物库，尤其是抗HIV药物8- C-抗坏血酸-（-）-表没食子儿茶素。
• Design of potent PPARα agonists
  作者：Per Sauerberg、John P. Mogensen、Lone Jeppesen、Paul S. Bury、Jan Fleckner、Grith S. Olsen、Claus B. Jeppesen、Erik M. Wulff、Pavel Pihera、Miroslav Havranek、Zdenek Polivka、Ingrid Pettersson

  DOI：10.1016/j.bmcl.2007.03.015

  日期：2007.6

  Computational analysis of the ligand binding pocket of the three PPAR receptor subtypes was utilized in the design of potent PPAR alpha agonists. Optimum PPAR alpha potency and selectivity were obtained with substituents having van der Waals volume around 260. Compound 6 had a PPAR alpha potency of 0.002 mu M and a selectivity ratio to PPAR gamma and PPAR delta of 410 and 2000, respectively. (C) 2007 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of a Series of Chiral AB₂ Monomers for Dendrimer Construction
  作者：James R. McElhanon、Mu-Jen Wu、Maya Escobar、Umer Chaudhry、Chun-Ling Hu、Dominic V. McGrath

  DOI：10.1021/jo961587w

  日期：1997.2.1

  Efficient preparation of a series of four chiral, nonracemic AB(2) monomers suitable for the construction of dendrimers is presented. Monomers 1-4 possess the common structural features of a diphenolic moiety and a benzylic or aliphatic hydroxyl which render these molecules suitable for convergent dendrimer synthesis. The same basic, high-yielding, five-step sequence is employed for 1-4. Stilbene derivatives 13 and 14 are prepared by a Horner-Wadsworth-Emmons modified Wittig reaction between 3,5- or 3,4-bis(benzyloxy)benzaldehyde (8 and 10) and an ester-substituted benzylphosphonate (11 or 12). Cinnamate derivatives 21 and 22 are prepared similarly from 8 and 10 and triethyl phosphonoacetate. Chirality is introduced in the form of a 1,2-diol unit by Sharpless asymmetric dihydroxylation (AD) (>97% ee in all cases), Protection of the 1,2-diols as their acetonide derivatives provides dioxolane intermediates 17, 18, 25, and 26. Reduction of the ester groups followed by hydrogenolysis of the benzyl ethers yields AB(2) monomers 1-4 in 57-67% overall yield from 8 and 10.