alpha-乙酰氧基苯基乙腈 | 5762-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: alpha-乙酰氧基苯基乙腈
• 中文别名: alpha-乙酰氧基苯乙腈
• 英文名称: cyano(phenyl)methyl acetate
• 英文别名: mandelonitrile acetate；[cyano(phenyl)methyl] acetate
• CAS: 5762-35-6
• 化学式: C₁₀H₉NO₂
• mdl: MFCD22205885
• 分子量: 175.187
• InChiKey: MUXDFYRMYMEGCM-UHFFFAOYSA-N

物化性质

• 熔点：
  207-210 °C
• 沸点：
  131 °C(Press: 12 Torr)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 储存条件：
  室温和干燥环境

反应信息

• 作为反应物：
  描述：

  alpha-乙酰氧基苯基乙腈 以 甲醇 为溶剂， 反应 2.0h， 以33.5%的产率得到α-甲基苯腈
  参考文献：
  名称：

  Katagi, Toshiyuki; Mikami, Nobuyoshi; Matsuda, Tadashi, Journal of the Chemical Society. Perkin transactions II, 1989, p. 779 - 782

  摘要：

  DOI：
• 作为产物：
  描述：

  2-nitro-1-phenylethyl acetate 在 三氯化磷 作用下， 以 吡啶 为溶剂， 生成 alpha-乙酰氧基苯基乙腈
  参考文献：
  名称：

  Novel cyano compounds

  摘要：

  一种新颖的共轭二烯双官能化过程，其中通过在酸酐存在下用硝酸处理共轭二烯，将硝基和以酯形式存在的羟基引入共轭二烯分子中。由此过程产生的和其转化产物的新颖化合物，可用作杀菌剂和杀真菌剂，并且是有价值的有机合成中间体。公开了一种用于生产腈和γ-乙酰氧基戊醛的新方法。

  公开号：

  US04079076A1

文献信息

• Probing the enantioselectivity of a diverse group of purified cobalt-centred nitrile hydratases
  作者：S. van Pelt、M. Zhang、L. G. Otten、J. Holt、D. Y. Sorokin、F. van Rantwijk、G. W. Black、J. J. Perry、R. A. Sheldon

  DOI：10.1039/c0ob01067g

  日期：——

  In this study a diverse range of purified cobalt containing nitrile hydratases (NHases, EC 4.2.1.84) from Rhodopseudomonas palustris HaA2 (HaA2), Rhodopseudomonas palustris CGA009 (009), Sinorhizobium meliloti 1021 (1021), and Nitriliruptor alkaliphilus (iso2), were screened for the first time for their enantioselectivity towards a broad range of chiral nitriles. Enantiomeric ratios of >100 were found for the NHases from HaA2 and CGA009 on 2-phenylpropionitrile. In contrast, the Fe-containing NHase from the well-characterized Rhodococcus erythropolis AJ270 (AJ270) was practically aselective with a range of different α-phenylacetonitriles. In general, at least one bulky group in close proximity to the α-position of the chiral nitriles seemed to be necessary for enantioselectivity with all NHases tested. Nitrile groups attached to a quaternary carbon atom were only reluctantly accepted and showed no selectivity. Enantiomeric ratios of 80 and >100 for AJ270 and iso2, respectively, were found for the pharmaceutical intermediate naproxennitrile, and 3-(1-cyanoethyl)benzoic acid was hydrated to the corresponding amide by iso2 with an enantiomeric ratio of >100.

  在本研究中，首次对来自红假单胞菌HaA2（HaA2）、红假单胞菌CGA009（009）、豌豆根瘤菌1021（1021）和嗜碱氮裂解菌（iso2）的多种纯化钴含氮裂解酶（NHases，EC 4.2.1.84）对一系列手性腈的立体选择性进行了筛选。对于2-苯基丙腈，来自HaA2和CGA009的NHases的立体异构比大于100。相比之下，来自已知红球菌AJ270（AJ270）的含铁NHase对一系列不同α-苯基乙腈实际上没有选择性。总的来说，对于所有测试的NHases来说，似乎至少需要一个在α-位附近的大体积基团才能实现立体选择性。连接在四级碳原子上的腈基团仅勉强被接受，并且没有显示出选择性。对于药物中间体萘普生腈，AJ270和iso2的立体异构比分别为80和大于100；iso2还将3-（1-氰乙基）苯甲酸水合为相应的酰胺，立体异构比大于100。
• Zinc Tetrafluoroborate-Catalyzed Efficient Conversion of Aldehydes to Geminal Diacetates and Cyanoacetates
  作者：Brindaban C. Ranu、Jyotirmoy Dutta、Arijit Das

  DOI：10.1246/cl.2003.366

  日期：2003.4

  A trace of an aqueous solution of zinc tetrafluoroborate was demonstrated to catalyze the conversion of an aldehyde to its 1,1-diacetate by acetic anhydride without any solvent. A similar reaction of an aldehyde with a mixture of potassium cyanide and acetic anhydride in methylene chloride was also catalyzed by Zn(BF4)2 to provide the corresponding geminal cyanoacetate.

  演示了一种含锌四氟硼酸盐的水溶液在无任何溶剂的情况下催化醛向其1,1-二乙酸酯的转化，该转化是通过乙酸酐实现的。类似地，在二氯甲烷中，醛与氰化钾和乙酸酐的混合反应也受到Zn(BF₄)₂的催化，生成相应的乙二酸酯。
• Naturally occurring cyanohydrins, analogues and derivatives as potential insecticides
  作者：Chris J Peterson、Rong Tsao、Joel R Coats

  DOI：10.1002/1526-4998(200007)56:7<615::aid-ps173>3.0.co;2-w

  日期：2000.7

  Several naturally occurring cyanohydrins were tested for fumigation toxicity to two insect species, the house fly (Musca domestica L) and the lesser grain borer (Rhyzopertha dominica (F)). Synthetic analogues of these compounds were tested as well. Most of the cyanohydrins tested were more toxic as fumigants to M domestica and R dominica than chloropicrin; some compounds were nearly as toxic as dichlorvos

  测试了几种天然存在的氰醇对两种昆虫物种的熏蒸毒性，即家蝇 (Musca domestica L) 和较小的谷物螟 (Rhyzopertha dominica (F))。还测试了这些化合物的合成类似物。大多数测试的氰醇作为熏蒸剂对家蝇和多米尼卡的毒性比氯化苦更大；有些化合物的毒性几乎与敌敌畏一样。天然存在的氰醇是测试中毒性最强的。
• Synthesis of Imidazoles and Oxazoles via a Palladium-Catalyzed Decarboxylative Addition/Cyclization Reaction Sequence of Aromatic Carboxylic Acids with Functionalized Aliphatic Nitriles
  作者：Ling Dai、Shuling Yu、Ningning Lv、Xuanzeng Ye、Yinlin Shao、Zhongyan Chen、Jiuxi Chen

  DOI：10.1021/acs.orglett.1c01762

  日期：2021.8.6

  efficient approach for the assembly of multiply substituted imidazoles and oxazoles in a single-step manner. These transformations are based on a decarboxylation addition and annulation of readily accessible aromatic carboxylic acids and aliphatic nitriles and exhibit good functional group compatibility and a high step economy. The reaction is scalable, and as-prepared products could be transformed into practical

  我们在此报告了一种以单步方式组装多取代咪唑和恶唑的有效方法。这些转化基于容易获得的芳香族羧酸和脂肪族腈的脱羧加成和环化，并表现出良好的官能团兼容性和高步骤经济性。该反应是可扩展的，制备的产品可以转化为实用的骨架。重要的是，莫罗替尼的后期衍生化突出了这种方法的潜在效用。
• Ionic liquids for enhancing the enantioselectivity of isolated BVMO-catalysed oxidations
  作者：Cristina Rodríguez、Gonzalo de Gonzalo、Marco W. Fraaije、Vicente Gotor

  DOI：10.1039/c0gc00560f

  日期：——

  The present study describes the first-time usage of an isolated thermostable Baeyer–Villiger monooxygenase (phenylacetone monooxygenase, PAMO) in the presence of ionic liquids. The stability, activity and selectivity of PAMO as an oxidative enzyme in the presence of different ionic liquids were studied. This revealed that the addition of some specific ionic liquids, such Ammoeng™ 102 and [bmim]MeSO4, can significantly enhance the E-value in the oxidation of racemic benzylketones. Moreover, the use of ionic liquids increases the optimal substrate concentration for performing Baeyer–Villiger oxidation, thereby extending the biocatalytic repertoire of PAMO for synthetic applications.

  本研究首次报道了在离子液体存在下使用分离的耐热贝耶尔-维利格单氧合酶（苯丙酮单氧合酶，PAMO）的情况。研究了不同离子液体存在下，PAMO作为氧化酶的稳定性、活性和选择性。结果显示，添加某些特定离子液体，如AmMOeng™ 102和[bmim]MeSO4，可以显著提高消旋苯甲酮氧化反应的E值。此外，离子液体的使用提高了进行贝耶尔-维利格氧化反应的最佳底物浓度，从而扩大了PAMO在合成应用中的生物催化范围。

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