ethyl 4-[(E)-2-[3,4-bis(phenylmethoxy)phenyl]ethenyl]benzoate | 186136-12-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: ethyl 4-[(E)-2-[3,4-bis(phenylmethoxy)phenyl]ethenyl]benzoate
• CAS: 186136-12-9
• 化学式: C₃₁H₂₈O₄
• 分子量: 464.561
• InChiKey: NSWZIVASBTWHPY-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 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 4-[(E)-2-[3,4-bis(phenylmethoxy)phenyl]ethenyl]benzoate 在 甲基磺酰胺 、 K2 、 potassium carbonate 、 对甲苯磺酸 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 50.0h， 生成 ethyl 4-[(4R,5R)-5-[3,4-bis(phenylmethoxy)phenyl]-2,2-dimethyl-1,3-dioxolan-4-yl]benzoate
  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：

  3,4-二苄氧基苯甲醛 、 ethyl 4-(diethoxyphosphorylmethyl)benzoate 在 sodium hydride 作用下， 生成 ethyl 4-[(E)-2-[3,4-bis(phenylmethoxy)phenyl]ethenyl]benzoate
  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

• 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.