(Z)-4-(4-methylphenylamino)pent-3-en-2-one | 56570-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-4-(4-methylphenylamino)pent-3-en-2-one
• 英文别名: (Z)-4-(p-tolylamino)pent-3-en-2-one；4-(4-methylphenylamino)pent-3-en-2-one；(3Z)-4-[(4-methylphenyl)amino]pent-3-en-2-one；(Z)-4-(4-methylanilino)pent-3-en-2-one
• CAS: 56570-34-4
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: ZQKBPMZILMKBHJ-NTMALXAHSA-N

物化性质

• 熔点：
  58-59 °C
• 沸点：
  313.0±42.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-4-(4-methylphenylamino)pent-3-en-2-one 在 sodium hydride 、 甲烷磺酰基叠氮化物 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以37%的产率得到1-(5-methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)ethanone
  参考文献：
  名称：

  一种新的高效制备1,2,3-三唑的方法

  摘要：

  通过与β-氨基-α，β-不饱和酮或酯以及甲苯磺酰基或甲磺酰基叠氮化物试剂进行重氮转移反应，可以容易地以中等至良好的产率获得1,2,3-三唑。在这种方法中，三唑环的氮原子N-2和N-3衍生自重氮转移试剂，氮原子N-1衍生自适当的烯胺。

  DOI：

  10.1016/s0040-4039(97)01137-4
• 作为产物：
  描述：

  乙烷,三氯氟- 、 乙酰丙酮 在 phosphotungstic acid (H₃PW₁₂O₄₀) 作用下， 反应 0.2h， 以95%的产率得到(Z)-4-(4-methylphenylamino)pent-3-en-2-one
  参考文献：
  名称：

  磷钨酸在无溶剂条件下催化合成β-烯氨基化合物

  摘要：

  在催化量的磷钨酸 (H3PW12O40, 1 mol%) 存在下，通过使 1,3-二羰基化合物与胺反应，开发了一种方便的环保程序，用于合成 β-烯胺酮和 β-烯胺酯。该反应在室温下无溶剂条件下顺利进行，并以高产率获得相应的 β-烯氨基化合物。

  DOI：

  10.3184/030823407x273488

文献信息

• [EN] NITROGEN TITANIUM COMPLEX, CATALYTIC SYSTEM COMPRISING SAID NITROGEN TITANIUM COMPLEX AND PROCESS FOR THE (CO)POLYMERIZATION OF CONJUGATED DIENES<br/>[FR] COMPLEXE D'AZOTE TITANE, SYSTÈME CATALYTIQUE COMPRENANT LEDIT COMPLEXE D'AZOTE TITANE ET PROCÉDÉ DE (CO)POLYMÉRISATION DE DIÈNES CONJUGUÉS
  申请人：VERSALIS SPA

  公开号：WO2017017203A1

  公开（公告）日：2017-02-02

  Nitrogen titanium complex having general formula (I) or (II), wherein: - R1 represents a hydrogen atom; or is selected from linear or branched C1-C20 alkyl groups, preferably C1-C15, optionally halogenated, cycloalkyl groups optionally substituted, aryl groups optionally substituted; - R2, R3, R4 and R5, identical or different, represent a hydrogen atom; or are selected from linear or branched C1-C20 alkyl groups, preferably C1-C15, optionally halogenated, cycloalkyl groups optionally substituted, aryl groups optionally substituted, nitro groups, hydroxyl groups, amino groups; - Y represents a NH-R6 group wherein R6 represents a hydrogen atom, or is selected from linear or branched C1-C20 alkyl groups, preferably C1-C15, optionally halogenated, cycloalkyl groups optionally substituted, aryl groups optionally substituted; or a N-R7 group wherein R7 is selected from linear or branched C1-C20 alkyl groups, preferably C1-C15, optionally halogenated, cycloalkyl groups optionally substituted, aryl groups optionally substituted; - X1, X 2, X 3 and X 4, identical or different, represent a halogen atom, such as, for example, chlorine, bromine, iodine, preferably chlorine; or are selected from linear or branched C1 -C20 alkyl groups, preferably C1-C15, -OCOR8 or -OR8 groups wherein R8 is selected from linear or branched C1-C20 alkyl groups, preferably C1-C15; or one of X1, X2 and X3 is selected from ethers, such as,for example, diethylether, tetrahydrofuran (THF), dimethoxyethane, preferably tetrahydrofuran (THF); - n is 1 in the case wherein Y represents a NH-R6 group wherein R6 has the same meanings reported above; or is 0 in the case wherein Y represents a N-R7 group wherein R7 has the same meanings reported above, or in the case wherein one of X1, X2 and X3 is selected from ethers; - R'1, R' 2, R'3, R'4, R'5, R'6 and R'7, identical or different, represent a hydrogen atom; or are selected from linear or branched C1-C20 alkyl groups, preferably C1-C15, optionally halogenated, cycloalkyl groups optionally substituted, aryl groups optionally substituted; - X'1 and X'2, identical or different, represent a halogen atom such as, for example, chlorine, bromine, iodine, preferably chlorine; or are selected from linear or branched C1-C20 alkyl groups, preferably C1-C15, -OCOR'8 groups or -OR'8 groups wherein R' 8 is selected from linear or branched C1-C20 alkyl groups, preferably C1-C15; - Y' is selected from ethers such as, for example,diethylether, tetrahydrofuran (THF), dimethoxyethane, preferably is tetrahydrofuran (THF); or Y' represents a group having general formula (III), wherein R'1, R' 2, R'3, R'4, R'5, R'6 and R'7, have the same meanings as reported above; - m is 0 or 1. Said nitrogen titanium complex having general formula (I) or (II) can be advantageously used in a catalytic system for the (co)polymerization of conjugated dienes.

  氮钛配合物的一般化学式为(I)或(II)，其中：- R1代表氢原子；或者选自线性或支链的C1-C20烷基，优选C1-C15，可选择卤代，环烷基可选择取代，芳基可选择取代；- R2、R3、R4和R5，相同或不同，代表氢原子；或选自线性或支链的C1-C20烷基，优选C1-C15，可选择卤代，环烷基可选择取代，芳基可选择取代，硝基，羟基，氨基；- Y代表NH-R6基团，其中R6代表氢原子，或选自线性或支链的C1-C20烷基，优选C1-C15，可选择卤代，环烷基可选择取代，芳基可选择取代；或N-R7基团，其中R7选自线性或支链的C1-C20烷基，优选C1-C15，可选择卤代，环烷基可选择取代，芳基可选择取代；- X1、X2、X3和X4，相同或不同，代表卤素原子，例如氯、溴、碘，优选氯；或选自线性或支链的C1-C20烷基，优选C1-C15，-OCOR8或-OR8基团，其中R8选自线性或支链的C1-C20烷基，优选C1-C15；或X1、X2和X3中的一个选自醚类化合物，例如二乙醚、四氢呋喃(THF)、二甲氧基乙烷，优选四氢呋喃(THF)；- n在Y代表NH-R6基团的情况下为1，其中R6具有上述相同含义；或在Y代表N-R7基团的情况下为0，其中R7具有上述相同含义，或在X1、X2和X3中的一个选自醚类化合物的情况下为0；- R'1、R'2、R'3、R'4、R'5、R'6和R'7，相同或不同，代表氢原子；或选自线性或支链的C1-C20烷基，优选C1-C15，可选择卤代，环烷基可选择取代，芳基可选择取代；- X'1和X'2，相同或不同，代表卤素原子，例如氯、溴、碘，优选氯；或选自线性或支链的C1-C20烷基，优选C1-C15，-OCOR'8基团或-OR'8基团，其中R'8选自线性或支链的C1-C20烷基，优选C1-C15；- Y'选自醚类化合物，例如二乙醚、四氢呋喃(THF)、二甲氧基乙烷，优选四氢呋喃(THF)；或Y'代表具有一般化学式(III)的基团，其中R'1、R'2、R'3、R'4、R'5、R'6和R'7具有上述相同含义；- m为0或1。具有一般化学式(I)或(II)的氮钛配合物可优势地用于共轭二烯的催化系统中的(共)聚合。
• Approach to Synthesis of β-Enamino Ketones and Pyrroles Catalyzed by Gallium(III) Triflate Under Solvent-Free Conditions
  作者：Jiuxi Chen、Xiaoliang Yang、Miaochang Liu、Huayue Wu、Jinchang Ding、Weike Su

  DOI：10.1080/00397910902898528

  日期：2009.11.5

  Abstract Metal triflates have been used to catalyze synthesis of β-enamino ketones or pyrroles from amines and 1,3-dicarbonyl or 1,4-dicarbonyl compounds under solvent-free conditions, respectively. Among different metal triflates screened, 0.5 mol% Ga(OTf)3 efficiently promoted the reactions to give excellent yields. In addition, the catalyst could be recovered easily after the reactions and reused

  摘要 金属三氟甲磺酸盐已用于在无溶剂条件下分别催化由胺和 1,3-二羰基或 1,4-二羰基化合物合成 β-烯氨基酮或吡咯。在筛选出的不同金属三氟甲磺酸盐中，0.5 mol% Ga(OTf)3 有效地促进了反应，获得了优异的产率。此外，催化剂在反应后很容易回收和重复使用，而不会明显损失活性。
• A General and Efficient Method for the Preparation of β-Enamino Ketones and Esters Catalyzed by Indium Tribromide
  作者：Zhan-Hui Zhang、Liang Yin、Yong-Mei Wang

  DOI：10.1002/adsc.200505268

  日期：2006.1

  A variety of β-enamino ketones and esters have been synthesized in high to exellent yields by reacting β-dicarbonyl compounds with amines in the presence of a catalytic amount of indium tribromide. The reaction proceeds smoothly at room temperature in a short reaction time under solvent-free conditions.

  在催化量的三溴化铟存在下，通过使β-二羰基化合物与胺反应，可以高产率地合成出多种β-烯胺酮和酯。在无溶剂条件下，反应在室温下以短的反应时间平稳地进行。
• Zinc Triflate Catalysed Synthesis of β-Enamino Ketones(Esters) under Solvent-Free Conditions
  作者：Chengliang Feng、Shuguang Zhang、Jin Cai、Junqing Chen、Huayou Hu、Min Ji

  DOI：10.3184/174751913x13787959859506

  日期：2013.10

  An efficient and mild procedure is described for the synthesis of a series of β-enamino ketones(esters) from 1,3-dicarbonyl compounds and aliphatic and aromatic amines using zinc triflate as the catalyst.

  描述了使用三氟甲磺酸锌作为催化剂从 1,3-二羰基化合物和脂肪族和芳香族胺合成一系列 β-烯氨基酮（酯）的有效和温和的程序。
• Synthesis of Pyrazoles, Diazepines, Enaminones, and Enamino Esters Using 12-Tungstophosphoric Acid as a Reusable Catalyst in Water
  作者：Zhicai Shang、Jun Wu、Xiang Chen、Jin She、Haifeng Wu、Peizhi Zhang

  DOI：10.1055/s-0028-1083169

  日期：——

  12-Tungstophosphoric acid (H3PW12O40) is found to be an efficient and recyclable catalyst in promoting a chemo- and re­gioselective condensation of hydrazines/hydrazides, diamines, and primary amines with various 1,3-dicarbonyl compounds in pure water at room temperature to afford pyrazoles, diazepines, and enaminones/enamino esters, respectively, in high yields.

  发现12-磷钨酸（H3PW12O40）是一种高效且可循环利用的催化剂，能够在纯水条件下、室温下促进肼/酰肼、二胺及伯胺与多种1,3-二羰基化合物进行化学选择性和区域选择性的缩合反应，分别高产率地生成吡唑、二氮杂环庚烷和烯胺酮/烯胺酯化合物。