2-(anthracen-9-yl)-2-hydroxyacetonitrile | 216966-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(anthracen-9-yl)-2-hydroxyacetonitrile
• 英文别名: 2-Anthracen-9-yl-2-hydroxyacetonitrile
• CAS: 216966-96-0
• 化学式: C₁₆H₁₁NO
• 分子量: 233.269
• InChiKey: BWLXHDKNDVUBRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  490.2±25.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(anthracen-9-yl)-2-hydroxyacetonitrile 在 盐酸 、 水 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 48.0h， 生成 methyl 2-(9-anthryl)-2-hydroxyacetate
  参考文献：
  名称：

  Sundholm, Oskari; Kanerva, Liisa T., ACH - Models in Chemistry, 1998, vol. 135, # 4, p. 625 - 640

  摘要：

  DOI：
• 作为产物：
  描述：

  9-乙烯基蒽 在 C₂₄H₂₃MnN₅O₅S₂ 、 氧气 、 异戊醛 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 2-(anthracen-9-yl)-2-hydroxyacetonitrile
  参考文献：
  名称：

  Mononuclear complexes of amide-based ligands containing appended functional groups: role of secondary coordination spheres on catalysis

  摘要：

  氨基配体与附加杂环环的配位化合物形成一个氢键结合的空腔，有效地结合底物。这种基于空腔的配合物可作为各种有机转化的可重复使用和非均相催化剂。

  DOI：

  10.1039/c4dt02079k

文献信息

• Three-Dimensional Heterometallic Coordination Networks: Syntheses, Crystal Structures, Topologies, and Heterogeneous Catalysis
  作者：Sumit Srivastava、Himanshu Aggarwal、Rajeev Gupta

  DOI：10.1021/acs.cgd.5b00697

  日期：2015.8.5

  This work presents the synthesis of Co3+-Zn2+} and Co3+-Cd2+} heterometallic coordination networks. These networks are originated from two unique Co3+-based metalloligands containing appended arylcarboxylic acid groups at the strategically placed positions. Such appended arylcarboxylate groups coordinate the secondary metal ions, Zn2+ and Cd2+, to afford distinct three-dimensional networks. All four networks display orderly arrangement of secondary metal ions and unique network topologies including an unprecedented one. These networks have been shown to act as the heterogeneous and reusable catalysts for the Knoevenagel condensation reactions and cyanation reactions of assorted aldehydes. Cyanation reactions nicely demonstrate the substrate size-exclusion catalysis.

  这项工作展示了Co3+-Zn2+}和Co3+-Cd2+}异金属配位网络的合成。这些网络源自两种独特的以Co3+为基础的金属配体，它们在战略性位置上附加了苯甲酸基团。这些附加的苯甲酸盐基团与次级金属离子Zn2+和Cd2+配位，形成了独特的三维网络结构。所有四种网络均呈现出次级金属离子的有序排列和独特的网络拓扑结构，其中包括一种前所未见的结构。这些网络已被证明可以作为异相和可重复使用的催化剂，用于Knoevenagel缩合反应和各种醛的氰化反应。氰化反应很好地展示了底物尺寸排除催化机制。
• A new (R)-hydroxynitrile lyase from Prunus mume: asymmetric synthesis of cyanohydrins
  作者：Samik Nanda、Yasuo Kato、Yasuhisa Asano

  DOI：10.1016/j.tet.2005.08.105

  日期：2005.11

  A new hydroxynitrile lyase (HNL) was isolated from the seed of Japanese apricot (Prunus mume). The enzyme has similar properties with HNL isolated from other Prunus species and is FAD containing enzyme. It accepts a large number of unnatural substrates (benzaldehyde and its variant) for the addition of HCN to produce the corresponding cyanohydrins in excellent optical and chemical yields. A new HPLC

  从日本杏（Prunus mume）的种子中分离出一种新的羟腈裂解酶（HNL ）。该酶与从其他李属物种中分离的HNL具有相似的特性，并且是含FAD的酶。它接受大量非天然底物（苯甲醛及其变体）以添加HCN，从而以优异的光学和化学收率生产相应的氰醇。针对该酶开发了一种新的基于HPLC的对映选择性测定技术，该技术可促进在缓冲溶液（pH = 4.5）中将KCN添加到苯甲醛中。
• CO ₂ ‐Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions**
  作者：Martin Juhl、Allan R. Petersen、Ji‐Woong Lee

  DOI：10.1002/chem.202003623

  日期：2021.1.4

  to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2‐mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani–Fischer synthesis under neutral conditions. This protocol offers an

  化学过程的热力学和动力学控制是获得所需产品和状态的关键。当无法获得所需产品时进行更改；可以用另外的试剂，催化剂和/或保护基来操纵反应。在这里，我们报告使用二氧化碳在不溶性氰化物源（KCN）的中性条件下加速氰醇合成，而不会产生有毒的HCN。在惰性气氛下，由于不利的平衡，该反应基本上不起作用。CO 2的效用扩大中性条件下的Kiliani–Fischer合成进一步展示了介导的选择性氰醇合成。通过简单地从烷基和芳基醛，KCN和大气压CO 2开始，该协议可轻松访问各种多元醇，氰醇，直链烷基腈。
• The biocatalyzed stereoselective preparation of polycyclic cyanohydrins
  作者：M.Manuel Cruz Silva、M.Luisa Sá e Melo、Marco Parolin、Davide Tessaro、Sergio Riva、Bruno Danieli

  DOI：10.1016/j.tetasy.2003.11.003

  日期：2004.1

  The enzyme-mediated preparation of enantiomerically or diastereomerically enriched polycyclic cyanohydrins has been investigated. Oxynitrilase-catalyzed cyanurations gave excellent results with the bicyclic aldehydes tested. On the other hand, enantio- or diastereoselective acylation, catalyzed by lipase PS or subtilisin, proved to be a more versatile methodology, giving good results even with sterically hindered polycyclic cyanohydrins. Specifically, the steroidal cyanohydrin derivative 4b was isolated with a 89% de. (C) 2003 Elsevier Ltd. All rights reserved.
• Prunus armeniaca hydroxynitrile lyase (ParsHNL)-catalyzed asymmetric synthesis of cyanohydrins from sterically demanding aromatic aldehydes
  作者：Rajib Bhunya、Tridib Mahapatra、Samik Nanda

  DOI：10.1016/j.tetasy.2009.05.022

  日期：2009.7

  Herein we report the biocatalytic asymmetric synthesis of cyanohydrins by using a new (R)-HNL from Prunus armeniaca. Several sterically demanding aromatic aldehydes which have never been used as substrates for any known HNLs are employed for the new (R)-HNL from A armeniaca, The cyanohydrins synthesized are obtained in good chemical yield with excellent enantioselectivities. (C) 2009 Elsevier Ltd. All rights reserved.