3-(naphthalen-2-yl)but-2-enenitrile | 128104-63-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(naphthalen-2-yl)but-2-enenitrile
• 英文别名: 3-Naphthalen-2-ylbut-2-enenitrile
• CAS: 128104-63-2
• 化学式: C₁₄H₁₁N
• 分子量: 193.248
• InChiKey: CUGCOOMMXDWMGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(naphthalen-2-yl)but-2-enenitrile 在 palladium on activated charcoal 盐酸羟胺 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 为溶剂， 80.0 ℃ 、344.73 kPa 条件下， 反应 2.25h， 生成 N'-hydroxy-3-naphthalen-2-ylbutanimidamide
  参考文献：
  名称：

  Antihyperglycemic activity of novel naphthalenylmethyl-3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. Substitution at the 1-, 5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4-[(5-Chloronaphthalen-2-yl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.

  DOI：

  10.1021/jm00069a006
• 作为产物：
  描述：

  氰甲基磷酸二乙酯 、 2-萘乙酮 在 sodium hydride 作用下， 生成 3-(naphthalen-2-yl)but-2-enenitrile
  参考文献：
  名称：

  Antihyperglycemic activity of novel naphthalenylmethyl-3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. Substitution at the 1-, 5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4-[(5-Chloronaphthalen-2-yl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.

  DOI：

  10.1021/jm00069a006

文献信息

• Asymmetric Hydrogenation of α,β-Unsaturated Nitriles with Base-Activated Iridium N,P Ligand Complexes
  作者：Marc-André Müller、Andreas Pfaltz

  DOI：10.1002/anie.201402053

  日期：2014.8.11

  Although many chiral catalysts are known that allow highly enantioselective hydrogenation of a wide range of olefins, no suitable catalysts for the asymmetric hydrogenation of α,β‐unsaturated nitriles have been reported so far. We have found that Ir N,P ligand complexes, which under normal conditions do not show any reactivity towards α,β‐unsaturated nitriles, become highly active catalysts upon addition

  尽管已知许多手性催化剂可以对多种烯烃进行高度对映选择性氢化，但迄今为止，尚未见有合适的催化剂可用于α，β-不饱和腈的不对称氢化。我们发现，在正常条件下对N，N-二异丙基乙胺加成的Ir N，P配位体络合物在对α，β-不饱和腈没有反应性的情况下变成高活性催化剂。碱活化的催化剂可以使H，2的α，β-不饱和腈共轭还原在低催化剂负载量下，可获得具有高转化率和出色对映选择性的相应饱和腈。相反，缺乏共轭氰基的烯烃在这些条件下不会发生反应，因此可以选择性还原α，β-不饱和腈的共轭CC键，而分子中其他类型的CC键则完好无损。 。
• <i>γ</i> ‐Functionalization of <i>α,β</i> ‐Unsaturated Nitriles under Mild Conditions: Versatile Synthesis of 4‐Aryl‐2‐Bromopyridines
  作者：Jaeuk Sim、Mayavan Viji、Jeongtae Rhee、Hyeju Jo、Suk Joon Cho、Yunjeong Park、Seung‐Yong Seo、Kwan‐Young Jung、Heesoon Lee、Jae‐Kyung Jung

  DOI：10.1002/adsc.201901002

  日期：2019.12.3

  synthesis of 4‐aryl‐2‐halopyridines via γ‐functionalization of α,β‐unsaturated nitriles, which were obtained by the HWE reaction with the corresponding ketones. The key features of our methods involve a conjugated γ‐enamine formation of α,β‐unsaturated nitrile (enamino nitrile), followed by consecutive intramolecular cyclization, resulting in heteroaromatic compounds like 2‐halopyridines, α‐pyrone, etc.

  该报告描述了通过α，β-不饱和腈的γ-官能化合成4-芳基-2-卤代吡啶，这些化合物是通过HWE反应与相应的酮获得的。我们方法的关键特征包括α，β-不饱和腈（烯氨基腈）的共轭γ-烯胺形成，随后连续的分子内环化，产生杂芳族化合物，如2-卤代吡啶，α-吡喃酮等。
• Antihyperglycemic activity of novel naphthalenylmethyl-3H-1,2,3,5-oxathiadiazole 2-oxides
  作者：John W. Ellingboe、Louis J. Lombardo、Thomas R. Alessi、Thomas T. Nguyen、Frieda Guzzo、Charles J. Guinosso、James Bullington、Eric N. C. Browne、Jehan F. Bagli

  DOI：10.1021/jm00069a006

  日期：1993.8

  A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. Substitution at the 1-, 5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4-[(5-Chloronaphthalen-2-yl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.