8-壬烯腈 | 5048-34-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 8-壬烯腈
• 英文名称: non-8-enenitrile
• 英文别名: 8-Nonenenitrile
• CAS: 5048-34-0
• 化学式: C₉H₁₅N
• 分子量: 137.225
• InChiKey: AFXXJCGHWSTDDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  8-壬烯腈 在 sodium hydroxide 、 水 作用下， 以 乙醇 、 水 为溶剂， 生成 8-壬烯酸
  参考文献：
  名称：

  Microwave-Assisted Cross-Metathesis of Unsaturated Thiocyanates: Application to the Synthesis of Thiocyanatins A and B and Analogues

  摘要：

  硫氰酸铂 B 和相关二硫代氰酸酯的合成是通过不饱和硫氰酸盐在钌催化剂的促进下进行交叉偏析来实现的。反应的效率在很大程度上取决于催化剂的性质、烯基链的长度和活化方式（传统加热或微波活化）。在后一种情况下，双键发生了异构化，改变了反应的进程。另外，硫氰酸盐 A 和 B 也分别只需三步和两步就能从现成的对甲苯磺酸盐中合成。

  DOI：

  10.1055/s-0029-1217089
• 作为产物：
  描述：

  8-壬烯醛 在 O-(4-(trifluoromethyl)benzoyl)hydroxylamine 、 (-)-CSA 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以84%的产率得到8-壬烯腈
  参考文献：
  名称：

  Direct Synthesis of Nitriles from Aldehydes Using an O-Benzoyl Hydroxylamine (BHA) as the Nitrogen Source

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.5b02547

文献信息

• [EN] SYNTHESIS OF STRAIGHT-CHAIN LEPIDOPTERAN PHEROMONES THROUGH ONE- OR TWO- CARBON HOMOLOGATION OF FATTY ALKENES<br/>[FR] SYNTHÈSE DE PHÉROMONES DE LÉPIDOPTÈRES À CHAÎNE DROITE PAR HOMOLOGATION D'UN OU DEUX ATOMES DE CARBONE D'ALCÈNES GRAS
  申请人：PROVIVI INC

  公开号：WO2020018581A1

  公开（公告）日：2020-01-23

  Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.

  描述了制备烯烃（包括昆虫信息素）的方法。这些方法包括使用1,3-二酯、环氧化物、氰乙酸盐和氰化物等试剂进行同系反应，通过增加一到两个碳原子来延长起始物质和中间体。这些烯烃包括在许多农业应用中有用的昆虫信息素。
• Synthesis of fused tetrazole- and imidazole derivatives via iodocyclization
  作者：Fredrik Ek、Lars-Göran Wistrand、Torbjörn Frejd

  DOI：10.1016/s0040-4020(03)00818-4

  日期：2003.8

  The possibility to prepare fused tetrazole- and imidazole derivatives by iodocyclization in moderate to excellent yields is demonstrated. In some examples the cyclizations were not following Baldwin's rules entirely, i.e. exo-selectivity. Nucleophilic substitution of the formed iodides gave different results depending on the hardness of the nucleophile. Thus, elimination of the iodide could be a problem

  证明了通过碘环化以中等至优异的产率制备稠合的四唑-和咪唑衍生物的可能性。在一些例子中，环化没有完全遵循鲍德温的规则，即外向选择性。取决于亲核试剂的硬度，所形成的碘化物的亲核取代产生不同的结果。因此，消除碘化物可能是一个问题，但是容许与黄原酸乙基钾的取代反应和使用丙烯腈的自由基反应。另外，我们表明可以在一种稠合的咪唑衍生物中分别选择性地使用三个碘取代基。
• Chemoselectivity in the chromium(II)-mediated synthesis of E-alkenylstannanes from aldehydes and Bu3SnCHBr2
  作者：David M. Hodgson、Lee T. Boulton、Graham N. Maw

  DOI：10.1016/s0040-4039(00)76805-5

  日期：1994.4

  The synthesis of functionalised E-alkenylstannanes from aldehydes and a mixture of Bu3SnCHBr2, LiI and CrCl2 is described.

  描述了由醛和Bu 3 SnCHBr 2，LiI和CrCl 2的混合物合成官能化的E-链烯基锡烷。
• Microwave-Assisted Cross-Metathesis of Unsaturated Thiocyanates: Application to the Synthesis of Thiocyanatins A and B and Analogues
  作者：Olivier Piva、Fanny Cros、Béatrice Pelotier

  DOI：10.1055/s-0029-1217089

  日期：2010.1

  The syntheses of thiocyanatin B and related dithiocyanates have been carried out by cross metathesis of unsaturated thiocyanates promoted by a ruthenium catalyst. The efficiency of the reaction depends strongly on the nature of the catalyst, the length of the alkenyl chain, and the mode of activation (conventional heating or microwave activation). In the later case, isomerization of double bonds took place and altered the course of the reaction. Alternatively, thiocyanatins A and B were synthesized by only a three-step and a two-step procedure, respectively, from readily available tosylates.

  硫氰酸铂 B 和相关二硫代氰酸酯的合成是通过不饱和硫氰酸盐在钌催化剂的促进下进行交叉偏析来实现的。反应的效率在很大程度上取决于催化剂的性质、烯基链的长度和活化方式（传统加热或微波活化）。在后一种情况下，双键发生了异构化，改变了反应的进程。另外，硫氰酸盐 A 和 B 也分别只需三步和两步就能从现成的对甲苯磺酸盐中合成。
• Scope of the chromium(II)-mediated synthesis of E-alkenylstannanes from aldehydes and Bu3SnCHBr2
  作者：David M Hodgson、Lee T Boulton、Graham N Maw

  DOI：10.1016/0040-4020(95)00086-n

  日期：1995.3

  The synthesis of E-alkenylstannanes from aldehydes and a mixture of Bu3SnCHBr2, LiI and CrCl2 is described. A mechanism is proposed to account for the alkene geometry in chromium(II)-mediated alkene synthesis which involves stereoselective addition by a gem-dichromium reagent to an aldehyde followed by a stereospecific elimination step.

  描述了由醛和Bu 3 SnCHBr 2，LiI和CrCl 2的混合物合成E-烯基锡烷。提出了一种机制来解释在铬（II）介导的烯烃合成中的烯烃几何结构，该机理包括通过宝石-二铬试剂向醛立体选择性加成到醛中，然后进行立体有择的消除步骤。