15-(Hydroxyimino)eburnan-14-one | 89825-99-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - Eburnan型生物碱
• 英文名称: 15-(Hydroxyimino)eburnan-14-one
• 英文别名: 5-(hydroxyimino)eburnan-14-one
• CAS: 89825-99-0
• 化学式: C₁₉H₂₁N₃O₂
• 分子量: 323.395
• InChiKey: SYSQNEXALGNFJH-MJGOQNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  57.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  15-(Hydroxyimino)eburnan-14-one 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of 15-methylene-eburnamonine from (+)-vincamine, evaluation of anticancer activity, and investigation of mechanism of action by quantitative NMR

  摘要：

  The biological role of installing a critical exocyclic enone into the structure of the alkaloid, (-)-eburnamonine, and characterization of the new chemical reactivity by quantitative NMR without using deuterated solvents are described. This selective modification to a natural product imparts potent anticancer activity as well as bestows chemical reactivity toward nucleophilic thiols, which was measured by quantitative NMR. The synthetic strategy provides an overall conversion of 40%. In the key synthetic step, a modified Peterson olefination was accomplished through the facile release of trifluoroacetate to create the requisite enone in the presence of substantial steric hindrance. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.095
• 作为产物：
  描述：

  长春布宁 在 亚硝酸特丁酯 、 potassium tert-butylate 作用下， 以 苯 为溶剂， 生成 15-(Hydroxyimino)eburnan-14-one
  参考文献：
  名称：

  Synthesis of 15-methylene-eburnamonine from (+)-vincamine, evaluation of anticancer activity, and investigation of mechanism of action by quantitative NMR

  摘要：

  The biological role of installing a critical exocyclic enone into the structure of the alkaloid, (-)-eburnamonine, and characterization of the new chemical reactivity by quantitative NMR without using deuterated solvents are described. This selective modification to a natural product imparts potent anticancer activity as well as bestows chemical reactivity toward nucleophilic thiols, which was measured by quantitative NMR. The synthetic strategy provides an overall conversion of 40%. In the key synthetic step, a modified Peterson olefination was accomplished through the facile release of trifluoroacetate to create the requisite enone in the presence of substantial steric hindrance. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.095

文献信息

• Synthesis of Vinca Alkaloids and Related Compounds, XXII. Some Chemical Transformations of 15-Oxovincamone
  作者：János Sápi、Lajos Szabó、Eszter Baitz-Gács、György Kalaus、Csaba Szántay、ÉVa Karsai-Bihátsi

  DOI：10.1002/jlac.198519850907

  日期：1985.9.12

  In the course of an attempted synthesis of E-norvincamine (4) (−)-15-oxovincamone (7), prepared from (−)-vincamone (2), was converted by means of methanolic sodium methoxide to give the (−)-11-cis and (±)-12-trans alcohols. Alkaline hydrolysis of the dioxo compound 7 furnishes the α-oxo acids 8 and 9 as a result of an epimerization-racemization process.

  在尝试合成的过程中，通过甲醇甲醇钠将由（-）-长春花酮（2）制备的E-去甲长春胺（4）（-）-15-氧代辛卡酮（7）转化为（-） - 11 -顺式和（±） - 12 -反式醇。由于差向异构-外消旋过程，二氧杂化合物7的碱性水解提供了α-氧杂酸8和9。