9-cyano-1-decyne | 87947-12-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 9-cyano-1-decyne
• 英文别名: 10-undecynonitrile；undec-10-ynenitrile；10-undecynenitrile
• CAS: 87947-12-4
• 化学式: C₁₁H₁₇N
• 分子量: 163.263
• InChiKey: AJLFOTODLOYHIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  9-cyano-1-decyne 在 三乙基铝 、 cobalt(II) 2-ethylhexanoate 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 2-(8-cyanooctyl)-5,6-octamethylenepyridine
  参考文献：
  名称：

  Cyclodimerization of ?.?-cyanoacetylenes, catalyzed by low-valence cobalt complexes

  摘要：

  DOI：

  10.1007/bf00954300
• 作为产物：
  描述：

  11-amino-1-undecyne 在 dichloro[1,3-bis(2-methylphenyl)-2-imidazolidinylidene](benzylidene) (tricyclohexylphosphine) ruthenium(II) 、 氧气 作用下， 以 甲苯 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 以23%的产率得到9-cyano-1-decyne
  参考文献：
  名称：

  有氧氧化伯胺和原位生成的胺与格鲁布斯催化剂从醛和铵盐中合成腈

  摘要：

  本文报道了格鲁布斯催化的伯胺的需氧氧化合成腈的路线。该反应可容纳多种底物，包括简单的伯胺，空间受阻的β，β-二取代胺，烯丙胺，苄胺和α-氨基酯。还指出了与各种官能团的反应相容性，特别是与烯烃，炔烃，卤素，酯，甲硅烷基醚和游离羟基的相容性。腈也是通过醛和NH 4 OAc原位生成的亚胺氧化合成的。

  DOI：

  10.1002/adsc.202000663

文献信息

• Direct Synthesis of Nitriles from Aldehydes Using an <i>O</i>-Benzoyl Hydroxylamine (BHA) as the Nitrogen Source
  作者：Xiao-De An、Shouyun Yu

  DOI：10.1021/acs.orglett.5b02547

  日期：2015.10.16

  The direct synthesis of nitriles from commercially available or easily prepared aldehydes has been achieved. O-(4-CF3-benzoyl)-hydroxylamine (CF3-BHA) was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes, which can be converted to a nitrile with the assistance of a Bronsted acid. Several aliphatic, aromatic, and alpha,beta-unsaturated nitriles that contain different functional groups were prepared in high yields (up to 94% yield). This method has notable advantages, such as simple and mild conditions, high yields, and good functional group tolerance.
• Highly Efficient and Catalytic Conversion of Aldoximes to Nitriles
  作者：Soon Ha Yang、Sukbok Chang

  DOI：10.1021/ol0168768

  日期：2001.12.1

  [GRAPHICS]Catalytic dehydration of aldoximes can be performed highly efficiently with a catalyst system of [RuCl2(p-cymene)](2)/molecular sieves under essentially neutral and mild conditions, and various types of cyano compounds are produced in good to excellent yields.
• SELIMOV, F. A.;XAFIZOV, V. R.;DZHEMILEV, U. M., IZV. AN CCCP. CEP. XIM., 1983, N 8, 1885-1887
  作者：SELIMOV, F. A.、XAFIZOV, V. R.、DZHEMILEV, U. M.

  DOI：——

  日期：——
• Nitrile Synthesis by Aerobic Oxidation of Primary Amines and <i>in</i>   <i>situ</i> Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst
  作者：Tatsuki Utsumi、Kenta Noda、Daichi Kawauchi、Hirofumi Ueda、Hidetoshi Tokuyama

  DOI：10.1002/adsc.202000663

  日期：2020.9.8

  reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β‐disubstituted amines, allylamine, benzylamines, and α‐amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of

  本文报道了格鲁布斯催化的伯胺的需氧氧化合成腈的路线。该反应可容纳多种底物，包括简单的伯胺，空间受阻的β，β-二取代胺，烯丙胺，苄胺和α-氨基酯。还指出了与各种官能团的反应相容性，特别是与烯烃，炔烃，卤素，酯，甲硅烷基醚和游离羟基的相容性。腈也是通过醛和NH 4 OAc原位生成的亚胺氧化合成的。
• Cyclodimerization of ?.?-cyanoacetylenes, catalyzed by low-valence cobalt complexes
  作者：F. A. Selimov、V. R. Khafizov、U. M. Dzhemilev

  DOI：10.1007/bf00954300

  日期：1983.8