Z-14-(pyridin-3-yl)-tetradec-4-en-1-oxime | 339169-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Z-14-(pyridin-3-yl)-tetradec-4-en-1-oxime
• CAS: 339169-11-8
• 化学式: C₁₉H₃₀N₂O
• 分子量: 302.46
• InChiKey: IHUPFXKBNQYGDP-VCQUAESLSA-N

物化性质

• 沸点：
  453.9±28.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  22.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  45.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Z-14-(pyridin-3-yl)-tetradec-4-en-1-oxime 在 sodium cyanoborohydride 、 sodium sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  On the synthesis of pyrinodemin A. Part 1: The location of the olefin

  摘要：

  The elucidation of the structure of the cytotoxic marine sponge alkaloid pyrinodemin A by synthesis is described. Based on the C-13 NMR spectra of three double bond positional isomers and the natural product, it is concluded the C14'-C15' isomer best represents the true structure of pyrinodemin A. In addition, the structural assignment of pyrinodemin C is evaluated. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.051
• 作为产物：
  描述：

  Z-14-(pyridin-3-yl)-tetradec-4-en-1-al 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 为溶剂， 以93%的产率得到Z-14-(pyridin-3-yl)-tetradec-4-en-1-oxime
  参考文献：
  名称：

  On the synthesis of pyrinodemin A. Part 1: The location of the olefin

  摘要：

  The elucidation of the structure of the cytotoxic marine sponge alkaloid pyrinodemin A by synthesis is described. Based on the C-13 NMR spectra of three double bond positional isomers and the natural product, it is concluded the C14'-C15' isomer best represents the true structure of pyrinodemin A. In addition, the structural assignment of pyrinodemin C is evaluated. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.051

文献信息

• Studies toward the Total Synthesis of the Cytotoxic Sponge Alkaloid Pyrinodemin A
  作者：Jack E. Baldwin、Stuart P. Romeril、Victor Lee、Timothy D. W. Claridge

  DOI：10.1021/ol015646q

  日期：2001.4.1

  [structure: see text]. The syntheses of the proposed structure of pyrinodemin A (1) and its cis double bond positional isomer (C15'-C16') in racemic form are described. The key reaction involved an intramolecular nitrone/double bond cycloaddition. Our results suggest that neither 1 nor its double positional isomer is the correct structure of pyrinodemin A

  [结构：见文字]。描述了拟除虫菊酯A（1）及其外消旋形式的顺式双键位置异构体（C15'-C16'）的合成。关键反应涉及分子内的硝酮/双键环加成。我们的结果表明，无论是1还是它的双重位置异构体都不是嘧啶A的正确结构
• Synthesis of pyrinodemins A and B. Assignment of the double bond position of pyrinodemin A
  作者：Barry B Snider、Bo Shi

  DOI：10.1016/s0040-4039(01)00003-x

  日期：2001.2

  Condensation of aldehyde 3a with hydroxylamine 4b afforded nitrone 2, which underwent an intramolecular cycloaddition to give Ib, the proposed structure of pyrinodemin A. A similar condensation of aldehyde 3a and hydroxylamine 4a provided pyrinodemin A (1a), which has the double bond one carbon further away from the isoxazolidine. An analogous sequence gave pyrinodemin B (21). (C) 2001 Elsevier Science Ltd. All rights reserved.