1,2,3,4,5,6,7,8-octahydroacridine-4-carbonitrile | 83246-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,2,3,4,5,6,7,8-octahydroacridine-4-carbonitrile
• 英文别名: 4-Cyano-1,2,3,4,5,6,7,8-octahydroacridine
• CAS: 83246-83-7
• 化学式: C₁₄H₁₆N₂
• 分子量: 212.294
• InChiKey: SOJIKZOLOLHKOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4,5,6,7,8-octahydroacridine-4-carbonitrile 在 溶剂黄146 、 sodium nitrite 作用下， 反应 0.5h， 以56%的产率得到4-nitro-1,2,3,4,5,6,7,8-octahydroacridine-4-carbonitrile
  参考文献：
  名称：

  八氢ac啶-4-腈（羧酰胺）与亲电试剂的反应

  摘要：

  已显示八氢ac啶-4-甲腈（羧酰胺）在酸性和中性介质中与芳基重氮盐和其他亲电试剂反应。反应发生在次甲基碳原子上，形成相应的4-官能化衍生物。所获得的偶氮化合物在140-155°С分解并消除了氮，得到了由自由基中间体反应形成的产物。

  DOI：

  10.1007/s10593-015-1703-8
• 作为产物：
  描述：

  1,2,3,4,5,6,7,8-八氢吖啶 、 二异丙基氨腈 在 正丁基锂 、 二异丙胺 作用下， 生成 1,2,3,4,5,6,7,8-octahydroacridine-4-carbonitrile
  参考文献：
  名称：

  Crossley, Roger; Shepherd, Robin G., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2479 - 2482

  摘要：

  DOI：

文献信息

• Process for preparing cyano derivatives of tetrahydroquinolines and
  申请人：John Wyeth & Brother Limited

  公开号：US04529798A1

  公开（公告）日：1985-07-16

  Fused carbocyclic ring derivatives of pyridine which contain a nitrile or thioamide group on the carbocyclic ring e.g. 8-cyano or thiocarboxamido-5,6,7,8-tetrahydroquinolines are prepared by a process in which a sodium, potassium, lithium or magnesium halide derivative of the pyridine compound is treated with a compound RaRbNCN wherein Ra and Rb are the same or different and represent alkyl, cycloalkyl, or aralkyl, or Ra and Rb are joined to form a heterocyclic ring with the nitrogen, and the product is treated with a proton source to obtain the nitrile which is optionally treated with a sulphurizing agent to form the thioamide. The nitriles or thioamides may be isolated as their acid addition salts.

  含有腈基或硫代酰胺基团的吡啶融合碳环衍生物，例如8-氰基或硫代羧酰胺基-5,6,7,8-四氢喹啉，可通过以下过程制备：用含有钠、钾、锂或镁卤化物衍生物的吡啶化合物处理化合物RaRbNCN，其中Ra和Rb相同或不同，代表烷基、环烷基或芳基，或Ra和Rb连接形成与氮原子相连的杂环环，然后用质子源处理产物以获得腈基，可选择用硫化剂处理腈基以形成硫代酰胺基团。腈基或硫代酰胺基团可作为其酸盐分离。
• Functionalization of tetra- and octahydroacridine derivatives through Michael addition
  作者：Ekaterina V. Zaliznaya、Oleg K. Farat、Svetlana A. Varenichenko、Alexander V. Mazepa、Victor I. Markov

  DOI：10.1016/j.tetlet.2016.06.096

  日期：2016.8

  octahydroacridine derivatives has been achieved using a Michael-type reaction with N-arylmaleimides. This method enables the facile synthesis of biologically important N-aryl or NH pyrrolidine-2,5-diones bearing tetra- or octahydroacridine moieties in a single step with high yields. The reactions of octahydroacridine-4-carboxamide with N-arylmaleimides react further to afford rearrangement products.

  四和八氢ac啶衍生物的无催化剂sp 3 C–H功能化已通过使用与N-芳基马来酰亚胺的迈克尔型反应实现。该方法能够以高收率一步简单地合成具有生物学上重要的具有四或八氢ac啶部分的N-芳基或NH吡咯烷-2，5-二酮。八氢ac啶-4-羧酰胺与N-芳基马来酰亚胺的反应进一步反应，得到重排产物。
• Process for preparing pyridine derivatives
  申请人：JOHN WYETH & BROTHER LIMITED

  公开号：EP0054384A1

  公开（公告）日：1982-06-23

  Fused carbocyclic ring derivatives of pyridine which contain a nitrile or thioamide group on the carbocyclic ring e.g. 8-cyano or thiocarboxamido-5,6,7,8-tetrahydro- quinolines are prepared by a process in which a sodium, potassium, lithium or magnesium halide derivative of the pyridine compound is treated with a compound RaRbNCN wherein Ra and Rb are the same or different and represent alkyl, cycloalkyl, or aralkyl, or Ra and Rb are joined to form a heterocyclic ring with the nitrogen, and the product is treated with a proton source to obtain the nitrile which is optionally treated with a sulphurising agent to form the thioamide. The nitriles or thioamides may be isolated as their acid addition salts.

  在碳环上含有腈基或硫酰胺基团的吡啶碳环衍生物，例如8-氰基或硫代羧酰胺基-5,6,7,8-四氢-喹啉的制备方法是：将吡啶化合物的钠、钾、锂或镁卤化物衍生物与化合物 RaRbNCN 一起处理，其中 Ra 和 Rb 可以相同或不同，代表烷基、环烷基或芳烷基，或 Ra 和 Rb 代表环烷基或芳烷基、环烷基或芳烷基，或者 Ra 和 Rb 与氮连接形成杂环，然后用质子源处理产物，得到腈，再用硫化剂处理形成硫代酰胺。腈或硫代酰胺可以作为它们的酸加成盐分离出来。
• Reactivity of Substituted 2-Spiropyrimidin-4-Ones Under Vilsmeier–Haack Conditions
  作者：S. A. Varenichenko、O. K. Farat、V. I. Markov

  DOI：10.1007/s10593-014-1626-9

  日期：2015.2

  Substituted 2-spiropyrimidin-4-ones are formylated at room temperature under the conditions of the Vilsmeier-Haack reaction. When cautiously heated they undergo electrophilic rearrangement.
• Rearrangement of 5’,6’,7’,8’-tetrahydro-1’H-spiro(cyclohexane-1,2’-quinazolin)-4’(3’H)-one during the Vilsmeier reaction
  作者：Victor I. Markov、Oleg K. Farat、Svetlana A. Varenichenko、Ekaterina V. Velikaya

  DOI：10.1016/j.mencom.2012.03.017

  日期：2012.3

  Treatment of 5,6',7',8'-tetrahydro-1'H-spiro(cyclohexane-1,2'-quinazolin)-4'(3'H)-one with POCl3 and DMF gives a mixture of 1,2,3,4,5,6,7,8-octahydroacridine-4-carbonitrile and 4,5-diformyl-2,3,6,7,8,10-hexahydroacridine-8a(1H)-carbonitrile, both products resulting from cascade transformations of the primary Vilsmeier intermediates.