methyl (2S)-3-[4-[(5-butyl-4-hydroxy-1-benzofuran-7-yl)oxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate | 865692-11-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: methyl (2S)-3-[4-[(5-butyl-4-hydroxy-1-benzofuran-7-yl)oxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 865692-11-1
• 化学式: C₂₇H₃₃NO₇
• 分子量: 483.562
• InChiKey: GTYROXQYRQDCLZ-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S)-3-[4-[(5-butyl-4-hydroxy-1-benzofuran-7-yl)oxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2S)-3-[4-[(4-acetyloxy-5-butyl-1-benzofuran-7-yl)oxy]phenyl]-2-[[(2S)-2-methoxy-2-phenylacetyl]amino]propanoate
  参考文献：
  名称：

  Synthesis of (S,S)-Isodityrosine by Dötz Benzannulation

  摘要：

  A synthesis of (S,S)-isodityrosine 1, a naturally occurring, key structural subunit of numerous biologically active macromolecules, is described. A formal [3 + 2 + 1] cycloaddition (Dotz benzannulation) approach was utilized to simultaneously construct an aromatic ring and the diaryl ether linkage in one step. This key step was extended to the synthesis of (S,S)-isodityrosine in two separate convergent synthetic routes. This method demonstrates a novel and mild method for the synthesis of diaryl ethers.

  DOI：

  10.1021/jo050363n
• 作为产物：
  描述：

  Boc-L-酪氨酸甲酯 、 1-己炔 、 alkaline earth salt of/the/ methylsulfuric acid 在 叔丁基锂 、 乙酰溴 作用下， 以 乙醚 、 二氯甲烷 、 四氢呋喃 为溶剂， 反应 22.0h， 生成 methyl (2S)-3-[4-[(5-butyl-4-hydroxy-1-benzofuran-7-yl)oxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  参考文献：
  名称：

  Synthesis of (S,S)-Isodityrosine by Dötz Benzannulation

  摘要：

  A synthesis of (S,S)-isodityrosine 1, a naturally occurring, key structural subunit of numerous biologically active macromolecules, is described. A formal [3 + 2 + 1] cycloaddition (Dotz benzannulation) approach was utilized to simultaneously construct an aromatic ring and the diaryl ether linkage in one step. This key step was extended to the synthesis of (S,S)-isodityrosine in two separate convergent synthetic routes. This method demonstrates a novel and mild method for the synthesis of diaryl ethers.

  DOI：

  10.1021/jo050363n

文献信息

• Synthesis of (<i>S</i>,<i>S</i>)-Isodityrosine by Dötz Benzannulation
  作者：Anuradha Gupta、Subhabrata Sen、Michael Harmata、Shon R. Pulley

  DOI：10.1021/jo050363n

  日期：2005.9.1

  A synthesis of (S,S)-isodityrosine 1, a naturally occurring, key structural subunit of numerous biologically active macromolecules, is described. A formal [3 + 2 + 1] cycloaddition (Dotz benzannulation) approach was utilized to simultaneously construct an aromatic ring and the diaryl ether linkage in one step. This key step was extended to the synthesis of (S,S)-isodityrosine in two separate convergent synthetic routes. This method demonstrates a novel and mild method for the synthesis of diaryl ethers.