<2-(1,2,3,4-tetrahydronaphthalenyl)>acetonitrile | 128104-99-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: <2-(1,2,3,4-tetrahydronaphthalenyl)>acetonitrile
• 英文别名: (1,2,3,4-tetrahydro-[2]naphthyl)-acetonitrile；(1,2,3,4-Tetrahydro-[2]naphthyl)-acetonitril；2-(1,2,3,4-Tetrahydronaphthalen-2-yl)acetonitrile
• CAS: 128104-99-4
• 化学式: C₁₂H₁₃N
• 分子量: 171.242
• InChiKey: ITFVUCWTNYHVNY-UHFFFAOYSA-N

物化性质

• 沸点：
  328.4±11.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  <2-(1,2,3,4-tetrahydronaphthalenyl)>acetonitrile 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 N'-hydroxy-2-(1,2,3,4-tetrahydronaphthalen-2-yl)ethanimidamide
  参考文献：
  名称：

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

  摘要：

  A series of substituted 3H-1,2,3,5-oxathiadiazole-2-oxides (6) was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. The oxathiadiazoles 6 were synthesized by a two-step sequence: treatment of a substituted acetonitrile (4) with hydroxylamine to give the corresponding amidoxime (5) and cyclization with thionyl chloride to yield 6. In terms of potency, the 2-naphthalenylmethyl group (as in compound 3) was found to be the optimal substituent in this series. Compound 3 was approximately 5 times more potent than ciglitazone (1).

  DOI：

  10.1021/jm00085a002
• 作为产物：
  描述：

  2-(3,4-二氢萘-2-基)乙腈 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以95%的产率得到<2-(1,2,3,4-tetrahydronaphthalenyl)>acetonitrile
  参考文献：
  名称：

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

  摘要：

  A series of substituted 3H-1,2,3,5-oxathiadiazole-2-oxides (6) was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. The oxathiadiazoles 6 were synthesized by a two-step sequence: treatment of a substituted acetonitrile (4) with hydroxylamine to give the corresponding amidoxime (5) and cyclization with thionyl chloride to yield 6. In terms of potency, the 2-naphthalenylmethyl group (as in compound 3) was found to be the optimal substituent in this series. Compound 3 was approximately 5 times more potent than ciglitazone (1).

  DOI：

  10.1021/jm00085a002

文献信息

• An Iodine-Catalyzed Hofmann-Löffler Reaction
  作者：Claudio Martínez、Kilian Muñiz

  DOI：10.1002/anie.201501122

  日期：2015.7.6

  and ecologically benign alternatives to transition metals, although their application as molecular catalysts in challenging CH oxidation reactions has remained elusive. An attractive iodine oxidation catalysis is now shown to promote the convenient conversion of carbon–hydrogen bonds into carbon–nitrogen bonds with unprecedented complete selectivity. The reaction proceeds by two interlocked catalytic

  碘试剂已被确认为过渡金属的经济和生态上的良性替代品，尽管它们在挑战CH氧化反应中作为分子催化剂的应用仍然难以捉摸。现在显示出有吸引力的碘氧化催化作用，以前所未有的完全选择性促进了碳氢键向碳氮键的便捷转化。该反应通过包括自由基链反应的两个互锁的催化循环进行，该自由基链反应由可见光作为能源引发。用于烷基的直接氧化胺化的这种非常规的合成策略没有生物合成优先权，并且提供了对一般类别的饱和氮化杂环的有效且直接的途径。
• Yokotsuka, Nippon Nogeikagaku Kaishi, 1949, vol. 23, p. 22,24
  作者：Yokotsuka

  DOI：——

  日期：——
• ALESSI, THOMAS R.;ELLINGBOE, JOHN W.
  作者：ALESSI, THOMAS R.、ELLINGBOE, JOHN W.

  DOI：——

  日期：——
• Antihyperglycemic activity of novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides
  作者：John W. Ellingboe、Thomas R. Alessi、Terence M. Dolak、Thomas T. Nguyen、John D. Tomer、Frieda Guzzo、Jehan F. Bagli、Michael L. McCaleb

  DOI：10.1021/jm00085a002

  日期：1992.4

  A series of substituted 3H-1,2,3,5-oxathiadiazole-2-oxides (6) was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. The oxathiadiazoles 6 were synthesized by a two-step sequence: treatment of a substituted acetonitrile (4) with hydroxylamine to give the corresponding amidoxime (5) and cyclization with thionyl chloride to yield 6. In terms of potency, the 2-naphthalenylmethyl group (as in compound 3) was found to be the optimal substituent in this series. Compound 3 was approximately 5 times more potent than ciglitazone (1).