Methyl 1-[3-[tert-butyl(dimethyl)silyl]oxy-4-cyanopent-4-enyl]-2-cyano-4-oxo-3-propan-2-ylcyclopent-2-ene-1-carboxylate | 956606-25-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Methyl 1-[3-[tert-butyl(dimethyl)silyl]oxy-4-cyanopent-4-enyl]-2-cyano-4-oxo-3-propan-2-ylcyclopent-2-ene-1-carboxylate
• 英文别名: methyl 1-[3-[tert-butyl(dimethyl)silyl]oxy-4-cyanopent-4-enyl]-2-cyano-4-oxo-3-propan-2-ylcyclopent-2-ene-1-carboxylate
• CAS: 956606-25-0
• 化学式: C₂₃H₃₄N₂O₄Si
• 分子量: 430.619
• InChiKey: LDFPMJOMTSAIOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 1-[3-[tert-butyl(dimethyl)silyl]oxy-4-cyanopent-4-enyl]-2-cyano-4-oxo-3-propan-2-ylcyclopent-2-ene-1-carboxylate 在 六甲基磷酰三胺 、 戴斯-马丁氧化剂 、 氟化氢吡啶 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  An Avenue to the Sordarin Core Adaptable to Analog Synthesis

  摘要：

  We describe a synthesis of ketones 3 (X = O-R or CN; Y = H or alkyl), which are useful building blocks for the preparation of analogs of the potent antifungal agent sordarin, 1. Congeners of 1 constructed from 3 should permit detailed SAR investigations of the terpenoid core of the natural product.

  DOI：

  10.1021/ol701547r
• 作为产物：
  描述：

  Methyl 1-(4-cyano-3-hydroxypent-4-enyl)-2-methoxy-4-oxo-3-propan-2-ylcyclopent-2-ene-1-carboxylate 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 12.5h， 生成 Methyl 1-[3-[tert-butyl(dimethyl)silyl]oxy-4-cyanopent-4-enyl]-2-cyano-4-oxo-3-propan-2-ylcyclopent-2-ene-1-carboxylate
  参考文献：
  名称：

  An Avenue to the Sordarin Core Adaptable to Analog Synthesis

  摘要：

  We describe a synthesis of ketones 3 (X = O-R or CN; Y = H or alkyl), which are useful building blocks for the preparation of analogs of the potent antifungal agent sordarin, 1. Congeners of 1 constructed from 3 should permit detailed SAR investigations of the terpenoid core of the natural product.

  DOI：

  10.1021/ol701547r

文献信息

• Synthetic Studies toward Sordarin: Building Blocks for the Terpenoid Core and for Analogues Thereof
  作者：Arnaud Schulé、Huan Liang、Jean-Pierre Vors、Marco A. Ciufolini

  DOI：10.1021/jo801911s

  日期：2009.2.20

  bi- and tricyclic building blocks for the elaboration of sordaricin and its analogues are described. The target molecules were obtained through inter- and intramolecular Diels−Alder reactions of a number of previously unknown cyclopentadienes. Unusual properties of 3-cyanoenones and 1-cyanocyclopentadienes have been unveiled and circumvented.

  描述了用于制造索达霉素及其类似物的双环和三环结构单元的途径。目标分子是通过许多先前未知的环戊二烯的分子间和分子内Diels-Alder反应获得的。3-氰基烯酮和1-氰基环戊二烯的不寻常特性已经被揭开并被规避。
• An Avenue to the Sordarin Core Adaptable to Analog Synthesis
  作者：Huan Liang、Arnaud Schulé、Jean-Pierre Vors、Marco A. Ciufolini

  DOI：10.1021/ol701547r

  日期：2007.10.1

  We describe a synthesis of ketones 3 (X = O-R or CN; Y = H or alkyl), which are useful building blocks for the preparation of analogs of the potent antifungal agent sordarin, 1. Congeners of 1 constructed from 3 should permit detailed SAR investigations of the terpenoid core of the natural product.