Oct-7-en-4-one N,N-Dimethylhydrazone | 117959-80-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Oct-7-en-4-one N,N-Dimethylhydrazone
• 英文别名: N-methyl-N-(oct-7-en-4-ylideneamino)methanamine
• CAS: 117959-80-5
• 化学式: C₁₀H₂₀N₂
• 分子量: 168.282
• InChiKey: HULXKNCPZZBJAX-UHFFFAOYSA-N

物化性质

• 沸点：
  220.8±33.0 °C(Predicted)
• 密度：
  0.81±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  12.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  15.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Oct-7-en-4-one N,N-Dimethylhydrazone 在 amberlyst-15 、 水 、 对苯醌 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.0h， 生成 octane-2,5-dione
  参考文献：
  名称：

  相邻基团参与路易斯酸促进的 [3 + 4] 和 [3 + 5] 环化。氧杂双环[3.n.1]烷-3-酮的合成

  摘要：

  路易斯酸用作 1,4- 和 1,5- 二羰基亲电试剂与 β-二酮和 β-酮酯的双（三甲基甲硅烷基）烯醇醚环化的催化剂。多种 2-(烷氧基碳)-m-氧杂双环[3.n.1]alkan-3-ones 可以通过该过程构建，其中产生两个新的碳-碳键。观察到异常高的区域控制，并且几乎可以在新碳环的每个位置实现良好到出色的立体化学控制。提出分子内相邻基团参与来解释在环化反应中获得的异常高的选择性

  DOI：

  10.1021/ja00056a002
• 作为产物：
  描述：

  2-戊酮 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 Oct-7-en-4-one N,N-Dimethylhydrazone
  参考文献：
  名称：

  Stereoselective synthesis of (.+-.)-indolizidines 167B, 205A, and 207A. Enantioselective synthesis of (-)-indolizidine 209B

  摘要：

  The first syntheses of the dendrobatid indolizidine alkaloids 167B (3), 205A (4), and 207A (5) are described using as a key step the highly stereoselective intramolecular nitrone cycloaddition of the (Z)-N-alkenylnitrone 10 to prepare the isoxazolidine 11. Mesylate-promoted cyclization of the alcohol 12, followed by reductive cleavage of the resulting mesylate salt, afforded the key axial hydroxymethyl compound 13, which was epimerized via the aldehyde to the equatorial alcohol, and was subsequently reduced to the required 8-methyl-substituted indolizidine. The feasibility of extending this strategy to the enantioselective synthesis of such alkaloids was demonstrated in the first synthesis of (-)-indolizidine 209B (6), whose nitrone precursor 10d was obtained from the (S)-glutamate-derived amine 40.

  DOI：

  10.1021/jo00004a012

文献信息

• Stereoselective synthesis of (.+-.)-indolizidines 167B, 205A, and 207A. Enantioselective synthesis of (-)-indolizidine 209B
  作者：Adrian L. Smith、Simon F. Williams、Andrew B. Holmes、Leslie R. Hughes、Colin. Swithenbank、Zev. Lidert

  DOI：10.1021/ja00234a021

  日期：1988.12
• Neighboring group participation in Lewis acid-promoted [3 + 4] and [3 + 5] annulations. The synthesis of oxabicyclo[3.n.1]alkan-3-ones
  作者：Gary A. Molander、Kimberly O. Cameron

  DOI：10.1021/ja00056a002

  日期：1993.2

  2-(alkoxycarbon)-m-oxabicyclo[3.n.1]alkan-3-ones can be constructed by this process in which two new carbon-carbon bonds are generated. Unusually high regioncontrol is observed, and good to excellent stereochemical control can be achieved at virtually every position on the new carbocycles. Intramolecular neighboring group participation is proposed to explain the unusually high selectivities attained in the annulation

  路易斯酸用作 1,4- 和 1,5- 二羰基亲电试剂与 β-二酮和 β-酮酯的双（三甲基甲硅烷基）烯醇醚环化的催化剂。多种 2-(烷氧基碳)-m-氧杂双环[3.n.1]alkan-3-ones 可以通过该过程构建，其中产生两个新的碳-碳键。观察到异常高的区域控制，并且几乎可以在新碳环的每个位置实现良好到出色的立体化学控制。提出分子内相邻基团参与来解释在环化反应中获得的异常高的选择性
• Stereoselective synthesis of (.+-.)-indolizidines 167B, 205A, and 207A. Enantioselective synthesis of (-)-indolizidine 209B
  作者：Andrew B. Holmes、Adrian L. Smith、Simon F. Williams、Leslie R. Hughes、Zev Lidert、Colin Swithenbank

  DOI：10.1021/jo00004a012

  日期：1991.2

  The first syntheses of the dendrobatid indolizidine alkaloids 167B (3), 205A (4), and 207A (5) are described using as a key step the highly stereoselective intramolecular nitrone cycloaddition of the (Z)-N-alkenylnitrone 10 to prepare the isoxazolidine 11. Mesylate-promoted cyclization of the alcohol 12, followed by reductive cleavage of the resulting mesylate salt, afforded the key axial hydroxymethyl compound 13, which was epimerized via the aldehyde to the equatorial alcohol, and was subsequently reduced to the required 8-methyl-substituted indolizidine. The feasibility of extending this strategy to the enantioselective synthesis of such alkaloids was demonstrated in the first synthesis of (-)-indolizidine 209B (6), whose nitrone precursor 10d was obtained from the (S)-glutamate-derived amine 40.