4-N-[(2R)-3,3-dimethylbutan-2-yl]-1-N-[5-[[[4-[N-[(2R)-3,3-dimethylbutan-2-yl]-C-hydroxycarbonimidoyl]-2,3-dihydroxyphenyl]-hydroxymethylidene]amino]naphthalen-1-yl]-2,3-dihydroxybenzene-1,4-dicarboximidic acid | 1510609-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-N-[(2R)-3,3-dimethylbutan-2-yl]-1-N-[5-[[[4-[N-[(2R)-3,3-dimethylbutan-2-yl]-C-hydroxycarbonimidoyl]-2,3-dihydroxyphenyl]-hydroxymethylidene]amino]naphthalen-1-yl]-2,3-dihydroxybenzene-1,4-dicarboximidic acid
• CAS: 1510609-60-5
• 化学式: C₃₈H₄₄N₄O₈
• 分子量: 684.789
• InChiKey: VHXSQFOSCUSZRZ-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  50
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  211
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Ga(acac)₃ 、 4-N-[(2R)-3,3-dimethylbutan-2-yl]-1-N-[5-[[[4-[N-[(2R)-3,3-dimethylbutan-2-yl]-C-hydroxycarbonimidoyl]-2,3-dihydroxyphenyl]-hydroxymethylidene]amino]naphthalen-1-yl]-2,3-dihydroxybenzene-1,4-dicarboximidic acid 、 potassium hydroxide 以 氘代甲醇 为溶剂， 反应 1.25h， 以78%的产率得到
  参考文献：
  名称：

  Chiral Amide Directed Assembly of a Diastereo- and Enantiopure Supramolecular Host and its Application to Enantioselective Catalysis of Neutral Substrates

  摘要：

  The synthesis of a novel supramolecular tetrahedral assembly of K12Ga4L6 stoichiometry is reported. The newly designed chiral ligand exhibits high diastereoselective control during cluster formation, leading exclusively to a single diastereomer of the desired host. This new assembly also exhibits high stability toward oxidation or a low pH environment and is a more robust and efficient catalyst for asymmetric organic transformations of neutral substrates.

  DOI：

  10.1021/ja411631v
• 作为产物：
  描述：

  2,3-Dimethoxy-4-(methoxycarbonyl)benzoylchlorid 在 三溴化硼 、 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 58.0h， 生成 4-N-[(2R)-3,3-dimethylbutan-2-yl]-1-N-[5-[[[4-[N-[(2R)-3,3-dimethylbutan-2-yl]-C-hydroxycarbonimidoyl]-2,3-dihydroxyphenyl]-hydroxymethylidene]amino]naphthalen-1-yl]-2,3-dihydroxybenzene-1,4-dicarboximidic acid
  参考文献：
  名称：

  Chiral Amide Directed Assembly of a Diastereo- and Enantiopure Supramolecular Host and its Application to Enantioselective Catalysis of Neutral Substrates

  摘要：

  The synthesis of a novel supramolecular tetrahedral assembly of K12Ga4L6 stoichiometry is reported. The newly designed chiral ligand exhibits high diastereoselective control during cluster formation, leading exclusively to a single diastereomer of the desired host. This new assembly also exhibits high stability toward oxidation or a low pH environment and is a more robust and efficient catalyst for asymmetric organic transformations of neutral substrates.

  DOI：

  10.1021/ja411631v

文献信息

• Impact of Host Flexibility on Selectivity in a Supramolecular Host-Catalyzed Enantioselective aza-Darzens Reaction
  作者：Stephen M. Bierschenk、Judy Y. Pan、Nicholas S. Settineri、Ulrike Warzok、Robert G. Bergman、Kenneth N. Raymond、F. Dean Toste

  DOI：10.1021/jacs.2c04182

  日期：2022.6.29
• Chiral Amide Directed Assembly of a Diastereo- and Enantiopure Supramolecular Host and its Application to Enantioselective Catalysis of Neutral Substrates
  作者：Chen Zhao、Qing-Fu Sun、William M. Hart-Cooper、Antonio G. DiPasquale、F. Dean Toste、Robert G. Bergman、Kenneth N. Raymond

  DOI：10.1021/ja411631v

  日期：2013.12.18

  The synthesis of a novel supramolecular tetrahedral assembly of K12Ga4L6 stoichiometry is reported. The newly designed chiral ligand exhibits high diastereoselective control during cluster formation, leading exclusively to a single diastereomer of the desired host. This new assembly also exhibits high stability toward oxidation or a low pH environment and is a more robust and efficient catalyst for asymmetric organic transformations of neutral substrates.