顺-2-戊烯腈 | 25899-50-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 顺-2-戊烯腈
• 中文别名: 2-戊烯腈；顺-2-戊烯
• 英文名称: cis-2-pentenenitrile
• 英文别名: (Z)-pent-2-enenitrile
• CAS: 25899-50-7
• 化学式: C₅H₇N
• 分子量: 81.1173
• InChiKey: ISBHMJZRKAFTGE-ARJAWSKDSA-N

物化性质

• 沸点：
  127-128 °C766 mm Hg(lit.)
• 密度：
  0.821 g/mL at 20 °C(lit.)
• 蒸气密度：
  2.8 (vs air)
• 闪点：
  75 °F
• 物理描述：
  Liquid
• 稳定性/保质期：

  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  6.1(a)
• 危险品标志：
  Xn,F,T
• 海关编码：
  2926909090
• 包装等级：
  II
• 危险类别：
  6.1(a)
• 危险品运输编号：
  UN 3276 6.1/PG 3
• 储存条件：
  密封于阴凉干燥环境中

反应信息

• 作为反应物：
  描述：

  顺-2-戊烯腈 在 aluminum oxide 、 氢气 作用下， 373.0 ℃ 、110.0 kPa 条件下， 生成 顺-2-戊烯
  参考文献：
  名称：

  The influence of carbon laydown on selectivity in the hydrogenation of pentenenitriles over supported-nickel catalysts

  摘要：

  Pentenenitriles contain two-reducible functionalities: a carbon-carbon double bond and a nitrile group, either of which may undergo hydrogenation during reaction. In this work we show how the deposition of hydrocarbonaceous material on the catalyst surface during pentenenitrile hydrogenation over 16 wt.% Ni/Al2O3 and 10 wt.% Ni/SiO2 catalysts has a significant impact on the observed catalytic activity and selectivity. The role of carbon laydown in controlling catalytic performance in this system has been evaluated through activity measurements and mechanistic studies employing a Tapered Element Oscillating Microbalance (TEOM) and a conventional flow-through reactor. TEOM data indicating the deposition of carbonaceous material during reaction are correlated with kinetic analysis which provides a description of catalyst deactivation in terms of the deactivation of groups of active sites. Specifically five distinct active sites are shown to exist on Ni/Al2O3 including a hydrogenation site on the support, which is not present in the case of Ni/SiO2. The nature and strength of these sites are discussed. Furthermore, deuteration studies provide mechanistic insights suggesting that the hydrogenation reaction proceeds via a cyclic intermediate. The reported data identify a correlation between mass laydown on specific active sites and deactivation, thereby demonstrating the influence of hydrocarbonaceous deposits on selectivity. Both the location and the nature of such deposits are crucial in determining its influence on reaction. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2010.06.036
• 作为产物：
  描述：

  1,2,3,6-四氢吡啶 在 N-氯代丁二酰亚胺 、 potassium carbonate 作用下， 生成 顺-2-戊烯腈
  参考文献：
  名称：

  5,6-dihydropyridine: synthesis and characterization

  摘要：

  DOI：

  10.1016/s0040-4039(01)91184-0

文献信息

• Regioselective biocatalytic hydrolysis of (E,Z)-2-methyl-2-butenenitrile for production of (E)-2-methyl-2-butenoic acid
  作者：Eugenia C Hann、Amy E Sigmund、Susan K Fager、Frederick B Cooling、John E Gavagan、Michael G Bramucci、Sarita Chauhan、Mark S Payne、Robert DiCosimo

  DOI：10.1016/j.tet.2003.10.120

  日期：2004.1

  Acidovorax facilis 72W nitrilase catalyzed the regioselective hydrolysis of (E,Z)-2-methyl-2-butenenitrile, producing only (E)-2-methyl-2-butenoic acid with no detectable conversion of (Z)-2-methyl-2-butenenitrile. (E)-2-Methyl-2-butenoic acid, produced in aqueous solution as the ammonium salt, was readily separated from (Z)-2-methyl-2-butenenitrile, and isolated in high yield and purity. The combination

  酸性嗜酸杆菌72W腈水解酶催化（E，Z）-2-甲基-2-丁烯腈的区域选择性水解，仅产生（E）-2-甲基-2-丁烯酸，而未检测到（Z）-2-甲基-丁烯的转化。2-丁腈。在水溶液中以铵盐形式生成的（E）-2-甲基-2-丁烯酸易于与（Z）-2-甲基-2-丁烯腈分离，并以高收率和纯度分离。腈水合酶和若干的酰胺酶活性的组合丛毛单胞睾丸酮菌株还可用于生产的（高度选择性ê）-2-甲基-2-丁从（酸ê，ž）-2-甲基-2-丁腈。
• Rhodium(II)-Catalyzed Reaction of Iodonium Ylides with Conjugated Compounds: Efficient Synthesis of Dihydrofurans, Oxazoles, and Dihydrooxepines
  作者：Yong Lee、Sang Yoon、Youngwan Seo、Bong Kim

  DOI：10.1055/s-2004-831257

  日期：——

  The rhodium(II)-catalyzed reaction of iodonium ylides with a variety of conjugated compounds has been examined. With α,β-unsaturated esters and α,β-unsaturated ketones, dihydrofurans were produced in moderate yields. Reactions with acrylonitriles yield oxazoles and dihydrofurans in moderate yields, whereas reactions with 1,3-butadienes result in dihydrofurans and dihydrooxepines in good yields, respectively

  已经检查了碘鎓叶立德与各种共轭化合物的铑 (II) 催化反应。使用 α,β-不饱和酯和 α,β-不饱和酮，以中等收率生产二氢呋喃。与丙烯腈反应以中等收率产生恶唑和二氢呋喃，而与 1,3-丁二烯反应分别以良好收率产生二氢呋喃和二氢氧杂环庚烷。形成这些产物的机理途径已根据环丙烷中间体或 1,3-偶极环加成机理进行了描述。
• A General and Efficient Heterogeneous Gold-Catalyzed Hydration of Nitriles in Neat Water under Mild Atmospheric Conditions
  作者：Yong-Mei Liu、Lin He、Miao-Miao Wang、Yong Cao、He-Yong He、Kang-Nian Fan

  DOI：10.1002/cssc.201200203

  日期：2012.8

  efficient catalyst for the selective hydration of a wide range of chemically diverse nitriles into valuable amides in neutral water, under mild atmospheric conditions (see image). The process shows promise for a facile and direct one‐pot synthesis of ε‐caprolactam, an industrially important molecule, starting from 6‐aminocapronitrile.

  温和，高效，通用：用纳米级金颗粒装饰的二氧化钛可在中性水中，在温和的大气条件下，将多种化学变化的腈选择性水合为有价值的酰胺，是一种有效的催化剂（见图）。该方法显示了从6-氨基己腈开始的一种工业上很重要的分子ε-己内酰胺的简便，直接的一锅合成的前景。
• Enantioselective Addition of Secondary Phosphines to Methacrylonitrile:  Catalysis and Mechanism
  作者：Aaron D. Sadow、Antonio Togni

  DOI：10.1021/ja0555163

  日期：2005.12.1

  (Pigiphos)nickel(II)-catalyzed reaction of secondary phosphines and methacrylonitrile gives chiral 2-cyanopropylphosphines in good yield and high enantiomeric excess (ee's up to 94%; (R)-(S)-Pigiphos = bis[(R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyl}cyclohexylphos phine). We propose a mechanism involving coordination of methacrylonitrile to the dicationic nickel catalyst followed by 1,4-addition of

  描述了高度对映选择性的分子间氢膦化反应。(Pigiphos) 镍 (II) 催化的仲膦和甲基丙烯腈的反应以良好的收率和高对映体过量（ee 高达 94%；(R)-(S)-Pigiphos = bis[(R) -1-[(S)-2-(二苯基膦基)二茂铁基]乙基}环己基膦)。我们提出了一种机制，涉及甲基丙烯腈与双阳离子镍催化剂的配位，然后是膦的 1,4-加成，然后是决定质子转移的速率。该机制得到 (a) 实验确定的速率定律 (rate = k'[Ni][甲基丙烯腈][t-Bu(2)PH])、(b) 大的初级氘同位素效应 k(H)/k 的支持(D) = 4.6(1) 对于在 28.3 摄氏度的甲苯-d(8) 中添加 t-Bu(2)PH(D)，
• A Facile Preparation of Aliphatic and Aromatic Primary Selenoamides Using 4-Methylselenobenzoate as a New Selenating Reagent
  作者：Hideharu Ishihara、Katsuhiro Yosimura、Mamoru Kouketsu

  DOI：10.1246/cl.1998.1287

  日期：1998.12

  Aliphatic and aromatic primary selenoamides 2 were isolated by the reaction of the corresponding aliphatic and aromatic nitriles with potassium 4-methylselenobenzoate in the presence of BF3·Et2O in moderate from high yields.

  脂肪族和芳香族伯硒酰胺 2 是通过相应的脂肪族和芳香族腈与 4-甲基硒苯甲酸钾在 BF3·Et2O 存在下以中等至高产率的反应分离的。

表征谱图