di-tert-butyl 1-(naphthalene-2-yl)hydrazine-1,2-dicarboxylate | 868394-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: di-tert-butyl 1-(naphthalene-2-yl)hydrazine-1,2-dicarboxylate
• 英文别名: di-tert-butyl 1-(naphthalen-2-yl)hydrazine-1,2-dicarboxylate；1,2-di-(1,1-dimethylethoxycarbonyl)-1-naphth-2-yl-hydrazine；1,2-bis(tert-butyloxycarbonyl)-1-(2-naphthyl)hydrazine；tert-butyl N-[(2-methylpropan-2-yl)oxycarbonylamino]-N-naphthalen-2-ylcarbamate
• CAS: 868394-40-5
• 化学式: C₂₀H₂₆N₂O₄
• 分子量: 358.437
• InChiKey: QWGJDRLIPQOFLR-UHFFFAOYSA-N

物化性质

• 熔点：
  132-133 °C
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 1-(naphthalene-2-yl)hydrazine-1,2-dicarboxylate 在 盐酸 作用下， 以 1,4-二氧六环 、 异丙醇 为溶剂， 反应 0.5h， 生成 2-萘肼盐酸盐
  参考文献：
  名称：

  Pyrazole Urea-Based Inhibitors of p38 MAP Kinase:  From Lead Compound to Clinical Candidate

  摘要：

  We report on a series of N-pyrazole, N'-aryl ureas and their mode of binding to p38 mitogen activated protein kinase. Importantly, a key binding domain that is distinct from the adenosine 5'-triphoshate (ATP) binding site is exposed when the conserved activation loop, consisting in part of Asp168-Phe169-Gly170, adopts a conformation permitting lipophilic and hydrogen bonding interactions between this class of inhibitors and the protein. We describe the correlation of the structure-activity relationships and crystallographic structures of these inhibitors with p38. In addition, we incorporated another binding pharmacophore that forms a hydrogen bond at the ATP binding site. This modification affords significant improvements in binding, cellular, and in vivo potencies resulting in the selection of 45 (BIRB 796) as a clinical candidate for the treatment of inflammatory diseases.

  DOI：

  10.1021/jm020057r
• 作为产物：
  描述：

  2-萘硼酸 、 di-tert-butyl (E)-azodicarboxylate 在 copper diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以93%的产率得到di-tert-butyl 1-(naphthalene-2-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  Copper Salt Catalyzed Addition of Arylboronic Acids to Azodicarboxylates

  摘要：

  [GRAPHIC]The addition of arylboronic acids 1 to azodicarboxylates 2 in the presence of a catalytic amount of a copper salt under mild reaction conditions gives aryl-substituted hydrazines 3 in high yields. The reaction is tolerant of a wide variety of functional groups.

  DOI：

  10.1021/jo051387x

文献信息

• An Efficient Pd-Catalyzed Coupling of Hydrazine Derivatives with Aryl Halides
  作者：Zhaoguo Zhang、Fang-Fang Ma、Zhi-Yong Peng、Wan-Fang Li、Xiao-Min Xie

  DOI：10.1055/s-0030-1260337

  日期：2011.10

  A convenient method for the intermolecular N-arylation of hydrazides with aryl halides in the presence of a palladium catalyst, a MOP-type ligand, and Cs2CO3 is reported. The reaction gives coupling products in good to excellent yields and has a high tolerance towards a wide spectrum of functional groups.

  报告了一种在钯催化剂、MOP 型配体和 Cs2CO3 的存在下用芳基卤化物对酰肼进行分子间 N-芳基化的简便方法。该反应生成的偶联产物收率良好甚至极佳，并且对多种官能团具有很高的耐受性。
• Amination of Arylboronic Compounds via the Copper-Catalyzed Addition of Arylboronic Esters to Azodicarboxylates
  作者：Naoto Chatani、Takeshi Uemura、Mao Yamaguchi

  DOI：10.1055/s-0035-1560468

  日期：——

  Abstract Arylboronic esters add to di-tert-butyl azodicarboxylate under mild reaction conditions (at room temperature) to afford aryl-substituted­ hydrazine derivatives in good yields. The reaction tolerates a wide variety of functional groups. Arylboronic esters add to di-tert-butyl azodicarboxylate under mild reaction conditions (at room temperature) to afford aryl-substituted­ hydrazine derivatives

  摘要 在温和的反应条件下（在室温下）将芳基硼酸酯加到偶氮二羧酸二叔丁酯中，以高收率得到芳基取代的肼衍生物。该反应可耐受多种官能团。 在温和的反应条件下（在室温下）将芳基硼酸酯加到偶氮二羧酸二叔丁酯中，以高收率得到芳基取代的肼衍生物。该反应可耐受多种官能团。
• Pyrazole Urea-Based Inhibitors of p38 MAP Kinase:  From Lead Compound to Clinical Candidate
  作者：John Regan、Steffen Breitfelder、Pier Cirillo、Thomas Gilmore、Anne G. Graham、Eugene Hickey、Bernhard Klaus、Jeffrey Madwed、Monica Moriak、Neil Moss、Chris Pargellis、Sue Pav、Alfred Proto、Alan Swinamer、Liang Tong、Carol Torcellini

  DOI：10.1021/jm020057r

  日期：2002.7.1

  We report on a series of N-pyrazole, N'-aryl ureas and their mode of binding to p38 mitogen activated protein kinase. Importantly, a key binding domain that is distinct from the adenosine 5'-triphoshate (ATP) binding site is exposed when the conserved activation loop, consisting in part of Asp168-Phe169-Gly170, adopts a conformation permitting lipophilic and hydrogen bonding interactions between this class of inhibitors and the protein. We describe the correlation of the structure-activity relationships and crystallographic structures of these inhibitors with p38. In addition, we incorporated another binding pharmacophore that forms a hydrogen bond at the ATP binding site. This modification affords significant improvements in binding, cellular, and in vivo potencies resulting in the selection of 45 (BIRB 796) as a clinical candidate for the treatment of inflammatory diseases.
• Copper Salt Catalyzed Addition of Arylboronic Acids to Azodicarboxylates
  作者：Takeshi Uemura、Naoto Chatani

  DOI：10.1021/jo051387x

  日期：2005.10.1

  [GRAPHIC]The addition of arylboronic acids 1 to azodicarboxylates 2 in the presence of a catalytic amount of a copper salt under mild reaction conditions gives aryl-substituted hydrazines 3 in high yields. The reaction is tolerant of a wide variety of functional groups.