N,N'-((1S,2S)-cyclohexane-1,2-diyl)bis(2-hydroxybenzamide) | 1166858-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-((1S,2S)-cyclohexane-1,2-diyl)bis(2-hydroxybenzamide)
• 英文别名: S,S-trans-1,2-bis(2-hydroxybenzamido)cyclohexane；2-hydroxy-N-[(1S,2S)-2-[(2-hydroxybenzoyl)amino]cyclohexyl]benzamide
• CAS: 1166858-97-4
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: ZIVDAOFTQGUZFD-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 N,N'-((1S,2S)-cyclohexane-1,2-diyl)bis(2-hydroxybenzamide) 、 三氯化铁 在 (C₂H₅)3N 作用下， 以 甲醇 为溶剂， 以73%的产率得到(S,S)-Fe(III)2(μ-OMe)2(1,3-bis(2-hydroxybenzamodo)cyclohexane)2
  参考文献：
  名称：

  Synthesis and characterization of a family of binuclear non-heme iron monooxygenase model compounds: Evidence for a “phenolate/amide carbonyl (PAC) shift” upon oxidation

  摘要：

  A series of binuclear iron compounds has been synthesized using diamide, bis-phenolate ligands in which the carbon-linker between the amide nitrogen atoms has been varied. Two diferrous compounds in the series, Fe-2(II)(H(2)Hbach)(2)(N-MeIM)(2) and Fe-2(II)(H(2)Hbame)(2)(N-MeIM)(2) along with their two-electron oxidized, di-mu-methoxy-bridged counterparts, Fe-III(H(2)Hbach)(2)(OMe)(2) and Fe-III(H(2)Hbame)(2)(OMe)(2) have been crystallographically characterized, as have the di-mu-methoxy compounds Fe-2(III)(H(2)Hbap)(2)(OMe)(2); Fe-2(III)(H(2)Hbabn)(2)(OMe)(2) and Fe-2(III)(H(2)Hbapen)(2)(OMe)(2) (H(2)Hbab = 1,2-bis(2-hydroxybenzamido) benzene, H(2)Hbach = trans-1,2-bis(2-hydroxybenzamido) cyclohexane, H(2)Hbame = 1,2-bis(2-hydroxybenzamido) ethane, H(2)Hbap = 1,3-bis(2-hydroxybenzamido) propane, H(2)Hbabn = 1,4-bis(2-hydroxybenzamido) butane, H(2)Hbapen = 1,5-bis(2-hydroxybenzamido) pentane, N-MeIM = N-methylimidazole and OMe = methoxide). Fe-2(II)(H(2)Hbach)(2)(N-MeIM)(2) and Fe-2(II)(H(2)Hbame)(2)(N-MeIM)(2) are structurally very similar to previously reported diferrous compounds of this family of ligands that have been shown to be active as oxygen atom transfer catalysts. Flexibility in the carbon-linker allows some variability in the orientation of the phenolate arms of the ligands in the diferric di-mu-methoxy compounds, but the Fe2O2 core remains largely unchanged across the series. Two-electron oxidation of the ferrous compounds in methanol shows a substantial ligand rearrangement that is consistent with other spectroscopic, electrochemical and kinetic investigations. The loss of both phenolate bridges upon oxidation is reminiscent of the "carboxylate shift" observed in binuclear non-heme enzymes and could provide insight into the driving force behind this family of compounds' function as a catalyst. (c) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2008.09.036
• 作为产物：
  描述：

  (1S,2S)-(+)-1,2-环己二胺 、 水杨酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 以51%的产率得到N,N'-((1S,2S)-cyclohexane-1,2-diyl)bis(2-hydroxybenzamide)
  参考文献：
  名称：

  Zn-ProPhenol 催化不对称炔烃加成的发展：手性炔丙醇的合成

  摘要：

  报告了一种通用且实用的锌催化对映选择性炔烃加成方法的开发。市售的 ProPhenol 配体 ( 1 ) 有助于以高产率和对映选择性将各种炔基锌添加到芳基、脂肪族和 α,β-不饱和醛中。对该反应机理的新见解导致试剂化学计量的显着减少，从而能够使用珍贵的炔烃并避免使用过量的二甲基锌。来自该反应的对映体富集的炔丙醇用作多功能合成中间体，并且能够有效合成多种复杂的天然产物。

  DOI：

  10.1002/chem.201202085

文献信息

• Development of Zn-ProPhenol-Catalyzed Asymmetric Alkyne Addition: Synthesis of Chiral Propargylic Alcohols
  作者：Barry M. Trost、Mark J. Bartlett、Andrew H. Weiss、Axel Jacobi von Wangelin、Vincent S. Chan

  DOI：10.1002/chem.201202085

  日期：2012.12.14

  The development of a general and practical zinc‐catalyzed enantioselective alkyne addition methodology is reported. The commercially available ProPhenol ligand (1) has facilitated the addition of a wide range of zinc alkynylides to aryl, aliphatic, and α,β‐unsaturated aldehydes in high yield and enantioselectivity. New insights into the mechanism of this reaction have resulted in a significant reduction

  报告了一种通用且实用的锌催化对映选择性炔烃加成方法的开发。市售的 ProPhenol 配体 ( 1 ) 有助于以高产率和对映选择性将各种炔基锌添加到芳基、脂肪族和 α,β-不饱和醛中。对该反应机理的新见解导致试剂化学计量的显着减少，从而能够使用珍贵的炔烃并避免使用过量的二甲基锌。来自该反应的对映体富集的炔丙醇用作多功能合成中间体，并且能够有效合成多种复杂的天然产物。
• Synthesis and characterization of a family of binuclear non-heme iron monooxygenase model compounds: Evidence for a “phenolate/amide carbonyl (PAC) shift” upon oxidation
  作者：Patrick J. Cappillino、Paul C. Tarves、Gerard T. Rowe、Andrew J. Lewis、Mark Harvey、Corina Rogge、Adonis Stassinopoulos、Wayne Lo、William H. Armstrong、John P. Caradonna

  DOI：10.1016/j.ica.2008.09.036

  日期：2009.5

  A series of binuclear iron compounds has been synthesized using diamide, bis-phenolate ligands in which the carbon-linker between the amide nitrogen atoms has been varied. Two diferrous compounds in the series, Fe-2(II)(H(2)Hbach)(2)(N-MeIM)(2) and Fe-2(II)(H(2)Hbame)(2)(N-MeIM)(2) along with their two-electron oxidized, di-mu-methoxy-bridged counterparts, Fe-III(H(2)Hbach)(2)(OMe)(2) and Fe-III(H(2)Hbame)(2)(OMe)(2) have been crystallographically characterized, as have the di-mu-methoxy compounds Fe-2(III)(H(2)Hbap)(2)(OMe)(2); Fe-2(III)(H(2)Hbabn)(2)(OMe)(2) and Fe-2(III)(H(2)Hbapen)(2)(OMe)(2) (H(2)Hbab = 1,2-bis(2-hydroxybenzamido) benzene, H(2)Hbach = trans-1,2-bis(2-hydroxybenzamido) cyclohexane, H(2)Hbame = 1,2-bis(2-hydroxybenzamido) ethane, H(2)Hbap = 1,3-bis(2-hydroxybenzamido) propane, H(2)Hbabn = 1,4-bis(2-hydroxybenzamido) butane, H(2)Hbapen = 1,5-bis(2-hydroxybenzamido) pentane, N-MeIM = N-methylimidazole and OMe = methoxide). Fe-2(II)(H(2)Hbach)(2)(N-MeIM)(2) and Fe-2(II)(H(2)Hbame)(2)(N-MeIM)(2) are structurally very similar to previously reported diferrous compounds of this family of ligands that have been shown to be active as oxygen atom transfer catalysts. Flexibility in the carbon-linker allows some variability in the orientation of the phenolate arms of the ligands in the diferric di-mu-methoxy compounds, but the Fe2O2 core remains largely unchanged across the series. Two-electron oxidation of the ferrous compounds in methanol shows a substantial ligand rearrangement that is consistent with other spectroscopic, electrochemical and kinetic investigations. The loss of both phenolate bridges upon oxidation is reminiscent of the "carboxylate shift" observed in binuclear non-heme enzymes and could provide insight into the driving force behind this family of compounds' function as a catalyst. (c) 2008 Elsevier B. V. All rights reserved.