3-(2-Chloro-6-nitrophenyl)-1,1-diphenylprop-2-yn-1-ol | 947409-45-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(2-Chloro-6-nitrophenyl)-1,1-diphenylprop-2-yn-1-ol
• CAS: 947409-45-2
• 化学式: C₂₁H₁₄ClNO₃
• 分子量: 363.8
• InChiKey: FTDHGYRHAIJGAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-Chloro-6-nitrophenyl)-1,1-diphenylprop-2-yn-1-ol 在 溶剂黄146 、 锌 作用下， 以 xylenes 为溶剂， 反应 38.0h， 生成 [2-(2-Amino-6-chlorophenyl)-3-methoxyphenyl]-diphenylmethanol
  参考文献：
  名称：

  WO2008/156656

  摘要：

  公开号：
• 作为产物：
  描述：

  2-氯-6-硝基苯甲醛 在 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 hexanes 为溶剂， 反应 5.67h， 生成 3-(2-Chloro-6-nitrophenyl)-1,1-diphenylprop-2-yn-1-ol
  参考文献：
  名称：

  WO2008/156656

  摘要：

  公开号：

文献信息

• Synthesis and Computational Analysis of Densely Functionalized Triazoles Using <i>o</i>-Nitrophenylalkynes
  作者：Melissa L. McIntosh、Ryne C. Johnston、Ommidala Pattawong、Bradley O. Ashburn、Michael R. Naffziger、Paul Ha-Yeon Cheong、Rich G. Carter

  DOI：10.1021/jo202467k

  日期：2012.1.20

  Dipolar cylcoadditions with azides using a series of o-nitrophenylethynes and disubstituted alkynes were studied experimentally and computationally. Density functional theory computations reveal the steric and electronic parameters that control the regioselectivity of these cycloadditions. Several new substrates were predicted that would either give enhanced regiocontrol or invert the regiochemical preference. Experimentally, the alkynes were screened in the [3 + 2] cycloaddition with benzyl azide. Of the 11 alkynes screened experimentally, the acetylenes containing halogen substitution directly on the alkyne provided the highest levels of regioselectivity. These haloalkynes were also shown to tolerate variation of the azide moiety with continued good levels of regioselectivity in most cases. Diverse functional groups can be incorporated through the cycloaddition process and their subsequent orthogonal modification was demonstrated.
• Diels−Alder Approach to Tetra-ortho-Substituted Biaryls Employing Propargylic Tertiary Alcohols as Dienophiles
  作者：Bradley O. Ashburn、Rich G. Carter

  DOI：10.1021/jo070812e

  日期：2007.12.1

  The efficient synthesis of a series of tetra-ortho-substituted biaryls is described utilizing a Diels-Alder reaction between propargylic tertiary alcohols and cyclic oxygenated dienes. The successful resolution of one of the biaryls is achieved through derivatization with menthyl chloroformate followed by crystallization. The menthyl carbamate is cleaved under basic conditions to reveal enantiomerically pure biaryl compounds.
• [EN] METHOD FOR MAKING BIARYL COMPOUNDS, COMPOUNDS MADE BY THE METHOD, AND METHOD FOR THEIR USE<br/>[FR] PROCÉDÉ DE FABRICATION DE COMPOSÉS BIARYLES, COMPOSÉS OBTENUS PAR LE PROCÉDÉ ET LEUR PROCÉDÉ D'UTILISATION
  申请人：OREGON STATE

  公开号：WO2008156656A2

  公开（公告）日：2008-12-24

  [EN] Certain disclosed embodiments of the present invention concern a method for making biaryl compounds by combining a diene with a dienophile under reaction conditions that facilitate a Diels-Alder reaction. Certain embodiments are particularly directed to making a tetra-ortho-substituted biaryl compounds. The disclosed method may involve using novel dienes, dienophiles, or both. Similarly, certain of the biaryl compounds are novel compounds too. Additional disclosed embodiments concern a method for making useful compounds by first making a Diels-Alder adduct. The Diels-Alder adduct is then further modified or coupled to other compounds. The method can be used to make carbazoles, such as Siamenol. Disclosed biaryl compounds are useful for a number of applications, such as pharmacophores and organocatalysts.
  [FR] Certains modes de réalisation décrits de la présente invention concernent un procédé de fabrication de composés biaryles par combinaison d'un diène avec un diénophile dans des conditions réactionnelles qui facilitent une réaction de Diels-Alder. Certains modes de réalisation se rapportent particulièrement à la fabrication de composés biaryles tétra-ortho-substitués. Le procédé décrit peut mettre en jeu l'utilisation de nouveaux diènes, diénophiles ou les deux. De façon analogue, certains des composés biaryles sont également des composés nouveaux. Des modes de réalisation décrits supplémentaires concernent un procédé pour fabriquer de composés utiles en réalisant tout d'abord un produit d'addition de Diels-Alder. Le produit d'addition de Diels-Alder est ensuite à nouveau modifié ou couplé à d'autres composés. Le procédé peut être utilisé pour fabriquer des carbazoles, tels que le Siaménol. Les composés biaryles décrits sont utiles pour un nombre d'applications, telles que des pharmacophores et des organocatalyseurs.