N-Boc-amino-(4'-methylphenyl)acetonitrile | 774225-33-1

• 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-Boc-amino-(4'-methylphenyl)acetonitrile
• 英文别名: tert-Butyl N-[cyano(4-methylphenyl)methyl]carbamate；tert-butyl N-[cyano-(4-methylphenyl)methyl]carbamate
• CAS: 774225-33-1
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: XTQHURFFZMGHMG-UHFFFAOYSA-N

物化性质

• 沸点：
  385.3±37.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Boc-amino-(4'-methylphenyl)acetonitrile 在 盐酸 、 sodium azide 、 三乙胺盐酸盐 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 44.0h， 生成 5-[1-(5-Ethyl-furan-2-yl)-meth-(Z)-ylidene]-2-{[(2H-tetrazol-5-yl)-p-tolyl-methyl]-amino}-thiazol-4-one
  参考文献：
  名称：

  Novel thiazolones as HCV NS5B polymerase allosteric inhibitors: Further designs, SAR, and X-ray complex structure

  摘要：

  Structure-activity relationships (SAR) of 1 against HCV NS5B polymerase were described. SAR explorations and further structure-based design led to the identifications of 2 and 3 as novel HCV NS5B inhibitors. X-ray structure of 3 in complex with NS5B polymerase was obtained at a resolution of 2.2A, and confirmed the design.

  DOI：

  10.1016/j.bmcl.2006.09.095
• 作为产物：
  描述：

  (Carbamoyl-p-tolyl-methyl)-carbamic acid tert-butyl ester 在 TEA 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以100%的产率得到N-Boc-amino-(4'-methylphenyl)acetonitrile
  参考文献：
  名称：

  Novel thiazolones as HCV NS5B polymerase allosteric inhibitors: Further designs, SAR, and X-ray complex structure

  摘要：

  Structure-activity relationships (SAR) of 1 against HCV NS5B polymerase were described. SAR explorations and further structure-based design led to the identifications of 2 and 3 as novel HCV NS5B inhibitors. X-ray structure of 3 in complex with NS5B polymerase was obtained at a resolution of 2.2A, and confirmed the design.

  DOI：

  10.1016/j.bmcl.2006.09.095

文献信息

• Copper-Promoted Cyclization of α-Amino Nitrile-Tethered Enynes: Controllable Synthesis of 3-Azabicyclo[4.1.0]hepta-2,4-dienes and 4,5-Dihydro-3<i>H</i>-azepines
  作者：Qiu-Qin Xu、Qi-Lan Hou、Wei Liu、Hai-Jing Wang、Wei-Wei Liao

  DOI：10.1021/acs.orglett.6b01864

  日期：2016.8.5

  The first example of Cu-promoted cyclization of α-amino nitrile-tethered enynes incorporating an electron-deficient alkene component is described. A wide range of functionalized 3-azabicyclo[4.1.0]hepta-2,4-dienes and 4,5-dihydro-3H-azepines were prepared efficiently in a controllable manner. Moreover, the diverse cascade process enables efficient incorporation of tertiary amine moieties under mild

  描述了结合有电子缺陷的烯烃组分的，Cu促进的α-氨基腈系联的烯炔的环化的第一个例子。以可控的方式有效地制备了各种官能化的3-氮杂双环[4.1.0]庚-2,4-二烯和4,5-二氢-3 H-氮杂。此外，多样的级联过程能够在温和的反应条件下有效地引入叔胺部分。在一系列对照实验的基础上，提出了一种可能的反应途径。
• Use of the Chiral Pool - Practical Asymmetric Organocatalytic Strecker Reaction with Quinine
  作者：Rüdiger Reingruber、Thomas Baumann、Stefan Dahmen、Stefan Bräse

  DOI：10.1002/adsc.200800798

  日期：2009.5

  Abstractmagnified imageAn efficient, organocatalytic enantioselective synthesis of N‐arylsulfonyl α‐amino nitriles from the corresponding α‐amido sulfones has been developed. This quinine‐catalyzed Strecker reaction provides the corresponding cyanated products in good yields and enantioselectivities.
• A Convenient Synthesis of<i>N</i>‐Boc‐Protected α‐Aminonitriles from α‐Amidosulfones
  作者：Vorawit Banphavichit、Saowaluk Chaleawlertumpon、Worawan Bhanthumnavin、Tirayut Vilaivan

  DOI：10.1081/scc-200028592

  日期：2004.1

  Synthesis of N-Boc-protected alpha-aminonitriles starting from N-Boc-protected alpha-aminosulfones is described. Treatment of the sulfone with two equivalents of potassium cyanide in 2-propanol or dichloromethane-H2O under phase transfer condition affords crystalline N-Boc-protected alpha-aminonitriles in good yield. Hydrolysis of the aminonitriles provides a convenient access to racemic a-amino acids.
• Novel thiazolones as HCV NS5B polymerase allosteric inhibitors: Further designs, SAR, and X-ray complex structure
  作者：Shunqi Yan、Gary Larson、Jim Z. Wu、Todd Appleby、Yili Ding、Robert Hamatake、Zhi Hong、Nanhua Yao

  DOI：10.1016/j.bmcl.2006.09.095

  日期：2007.1

  Structure-activity relationships (SAR) of 1 against HCV NS5B polymerase were described. SAR explorations and further structure-based design led to the identifications of 2 and 3 as novel HCV NS5B inhibitors. X-ray structure of 3 in complex with NS5B polymerase was obtained at a resolution of 2.2A, and confirmed the design.