Methyl 4-acetyloxy-4-cyano-2-methylidene-4-phenylbutanoate | 1346232-08-3

• 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: Methyl 4-acetyloxy-4-cyano-2-methylidene-4-phenylbutanoate
• CAS: 1346232-08-3
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: IERHBBDYKSHHNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 4-acetyloxy-4-cyano-2-methylidene-4-phenylbutanoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以77%的产率得到methyl 3-benzoyl-2-(cyanomethyl)-4-oxopentanoate
  参考文献：
  名称：

  Lewis Base-Promoted Rearrangement of Allylic Cyanohydrins: Construction of Functionalized Nitriles Bearing 1,3-Diketone Moieties

  摘要：

  A novel Lewis base-promoted rearrangement of allylic cyanohydrins has been developed, in which the cyano group was rearranged, directly coupled with the generation of new functional groups. This protocol provides a unique and facile way to prepare highly functionalized nitriles bearing 1,3-diketone moieties under mild reaction conditions. Furthermore, the synthetic transformations of the functionalized products have also been demonstrated.

  DOI：

  10.1021/jo501909w
• 作为产物：
  描述：

  methyl 2-(((tert-butoxycarbonyl)oxy)methyl)acrylate 、 alpha-乙酰氧基苯基乙腈 在 三乙烯二胺 作用下， 以 乙腈 为溶剂， 生成 Methyl 4-acetyloxy-4-cyano-2-methylidene-4-phenylbutanoate
  参考文献：
  名称：

  Lewis Base Promoted Intramolecular Acylcyanation of α-Substituted Activated Alkenes: Construction of Ketones Bearing β-Quaternary Carbon Centers

  摘要：

  A novel phosphine-promoted intramolecular acylcyanation of alpha-substituted activated alkenes has been developed, which provides a unique access to densely functionalized acyclic ketones bearing beta-quaternary carbon centers with a remarkable feature that both alpha- and beta-positions of activated alkene are functionalized.

  DOI：

  10.1021/ol3007716

文献信息

• Construction of Highly Functional Quaternary Carbon Stereocenters <i>via</i> an Organocatalytic Tandem Cyanation–Allylic Alkylation Reaction
  作者：Zhe Zhuang、Feng Pan、Jian-Guo Fu、Jian-Ming Chen、Wei-Wei Liao

  DOI：10.1021/ol202499g

  日期：2011.12.2

  The first tertiary amine-catalyzed tandem cyanation-allyic alkylation (CAA) reaction of aldehydes, appropriate cyanide sources, and Morita-Baylis-Hillman (MBH) adducts has been developed, which provides a facile access to densely functionalized products containing O-substituted quaternary centers.