α-(p-Toluoyl)-zimtsaeurenitril | 64646-27-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: α-(p-Toluoyl)-zimtsaeurenitril
• 英文别名: 2-(4-methylbenzoyl)-3-phenylprop-2-enenitrile
• CAS: 64646-27-1
• 化学式: C₁₇H₁₃NO
• 分子量: 247.296
• InChiKey: LOMVIEJUNMFYQX-UHFFFAOYSA-N

物化性质

• 熔点：
  95-96 °C(Solv: ethanol (64-17-5))
• 沸点：
  422.5±45.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  α-(p-Toluoyl)-zimtsaeurenitril 在 哌啶 、 硫酸 、 sodium nitrite 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 42.0h， 生成 2-hydroxy-4-phenyl-6-p-tolyl-pyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  Seoane, Carlos; Soto, Jose L.; Zamorano, Pilar, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 309 - 314

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲基苯甲酸乙酯 在 哌啶 、 sodium hydride 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 19.0h， 生成 α-(p-Toluoyl)-zimtsaeurenitril
  参考文献：
  名称：

  Tandem cross-Rauhut–Currier/cyclization reactions of activated alkenes to give densely functionalized 3,4-dihydropyrans

  摘要：

  A novel tandem cross-Rauhut-Currier/cyclization reaction between alpha,beta-unsaturated ketones was developed. Using DABCO (20 mol %) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative catalytic cycle was proposed with key intermediates confirmed by ESIMS studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.036

文献信息

• Substituent‐Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and <i>Oxa</i> ‐Bridged Fused Heterocycles
  作者：Tianlong Zeng、Jingyang Kong、Hongkai Wang、Lingyan Liu、Weixing Chang、Jing Li

  DOI：10.1002/adsc.202100523

  日期：2021.8.13

  Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the

  在此，我们报告了在 PtI 2存在下查耳酮和芳基炔醇的取代基控制的发散级联环加成反应。根据查耳酮上的取代基，在相同的反应条件下，可以以 86-97% 和 87-95% 的产率获得螺缩酮或氧杂桥连的稠合杂环。进行对照实验以阐明高化学选择性的起源。这些为合成各种结构复杂的含氧杂环提供了一种方法。
• Organocatalytic Asymmetric [4+2] Cycloaddition of 1-Acetylcyclopentene and 1-Acetylcyclohexene for the Synthesis of Fused Carbocycles
  作者：Utpal Nath、Subhas Chandra Pan

  DOI：10.1002/ejoc.201701238

  日期：2017.11.24

  The first organocatalytic asymmetric [4+2] cycloaddition reaction employing 1-acetylcyclopentene and 1-acetylcyclohexene is described. Enones having cyano group are used as the dienophile partner in this method. The reaction provides a useful practical route for the synthesis of bicyclic fused carbocycles having four contiguous stereocentres.

  描述了使用 1-乙酰环戊烯和 1-乙酰环己烯的第一个有机催化不对称 [4+2] 环加成反应。在该方法中使用具有氰基的烯酮作为亲二烯体伙伴。该反应为合成具有四个连续立体中心的双环稠合碳环提供了一条有用的实用途径。
• Magnesium Halide‐Catalyzed Synthesis of Oxaspiro[2.5]octenes from a Methylenecyclopropane and Acyl Cyanoalkenes
  作者：Itaru Suzuki、Kazuki Ogura、Jun‐ya Shimazu、Ikuya Shibata

  DOI：10.1002/ejoc.202100500

  日期：2021.5.20

  Novel transformation of methylenecyclopropanes (MCPs) with acyl cyanoalkenes has been achieved to give oxaspiro[2.5]octenes. This annulation is successfully catalyzed by magnesium halides under mild reaction conditions, and shows a broad functional group tolerance. The reaction includes a rare reaction course, which involves an intramolecular oxa-Michael addition of Mg enolate after the ring opening

  已经实现了用酰基氰基烯烃对亚甲基环丙烷（MCPs）的新型转化，从而生成了氧杂螺[2.5]辛烯。在温和的反应条件下，这种环化反应成功地由卤化镁催化，并显示出宽泛的官能团耐受性。该反应包括一个罕见的反应过程，该过程涉及在MCP开环后分子内将Mg烯醇氧加到Oxa-Michael并加到烯烃中。没有在我们的实验室中以前观察到的典型的分子内烯醇镁的迈克尔加成反应，导致形成螺[2.3]己烷。
• Substrate-controlled switchable asymmetric annulations to access polyheterocyclic skeletons
  作者：Kai-Kai Wang、Pan Wang、Qin Ouyang、Wei Du、Ying-Chun Chen

  DOI：10.1039/c6cc06148f

  日期：——

  domino process from Morita-Baylis-Hillman carbonates of isatins and acrylate and [small alpha]-cyano-[small alpha],[small beta]-unsaturated ketones to deliver highly enantioenriched tetrahydrofuro[2',3':4,5]pyrano[2,3-b]indoles was disclosed catalysed by cinchona-derived tertiary amines, involving [small alpha]-regioselective cyclopropanation, ring-opening,...

  靛红和丙烯酸的Morita-Baylis-Hillman碳酸盐和[小α]-氰基-[小α]，[小β]-不饱和酮的出乎意料的多米诺法，可以提供高度对映体富集的四氢呋喃[2'，3'：4,5公开了由金鸡纳衍生的叔胺催化的]吡喃并[2,3-b]吲哚，涉及[小α]-区域选择性环丙烷化，开环，...。
• Divergent Phosphine-Catalyzed [2+4] or [3+2] Cycloaddition Reactions of γ-Substituted Allenoates with Oxadienes
  作者：Erqing Li、Meijia Chang、Ling Liang、You Huang

  DOI：10.1002/ejoc.201403369

  日期：2015.2

  of the phosphine catalysts, the γ-substituted allenoates selectively acted as C3 or C2 synthons. Under the catalysis of different organophosphine catalysts, the domino reaction proceeded smoothly with broad substrate tolerance and excellent total yields. The results suggest that the ethyl group of the γ-substituted allenoates played a key role in the domino reaction.

  开发了一种策略，通过使用不同的膦催化剂，从相同的起始材料构建二氢吡喃和多功能环戊烯衍生物。通过利用膦催化剂的不同亲核性，γ-取代的烯丙酸酯选择性地充当 C3 或 C2 合成子。在不同有机膦催化剂的催化下，多米诺反应顺利进行，具有广泛的底物耐受性和优异的总收率。结果表明，γ-取代的烯丙酸酯的乙基在多米诺反应中起关键作用。