N-(9H-fluoren-9-ylidene)ethanamine | 64605-46-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9H-fluoren-9-ylidene)ethanamine
• 英文别名: N-ethyl-9H-fluoren-9-imine；ethyl-fluoren-9-yliden-amine；Aethyl-fluoren-9-yliden-amin；N-Ethylfluorenimin；N-ethylfluoren-9-imine
• CAS: 64605-46-5
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: YFJHEQQVFDYFCY-UHFFFAOYSA-N

物化性质

• 熔点：
  206 °C (decomp)
• 沸点：
  339.1±15.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(9H-fluoren-9-ylidene)ethanamine 在 间氯过氧苯甲酸 作用下， 以 氘代甲醇 为溶剂， 反应 2.0h， 以100%的产率得到2'-Ethylspiro[fluorene-9,3'-oxaziridine]
  参考文献：
  名称：

  Boyd, Derek R.; Coulter, Peter B.; McGuckin, M. Rosaleen, Journal of the Chemical Society. Perkin transactions I, 1990, # 2, p. 301 - 306

  摘要：

  DOI：
• 作为产物：
  描述：

  9,9-联亚茀 在 乙醇 作用下， 生成 N-(9H-fluoren-9-ylidene)ethanamine
  参考文献：
  名称：

  Interaction of Amines and Ammonia with Dibiphenyleneethylene

  摘要：

  DOI：

  10.1021/ja01315a022

文献信息

• Boyd, Derek R.; Coulter, Peter B.; Hamilton, Robert, Journal of the Chemical Society. Perkin transactions I, 1985, p. 2123 - 2128
  作者：Boyd, Derek R.、Coulter, Peter B.、Hamilton, Robert、Thompson, Norris T.、Sharma, Narain D.、Stubbs, Michael E.

  DOI：——

  日期：——
• Chen, Yi-Jing; Seki, Kazutaka; Yamashita, Yasuhiro, Journal of the American Chemical Society, 2010, vol. 132, p. 3244 - 3245
  作者：Chen, Yi-Jing、Seki, Kazutaka、Yamashita, Yasuhiro、Kobayashi, Shu

  DOI：——

  日期：——
• Normal, abnormal and pseudo-abnormal reaction pathways for the imine-peroxyacid reaction
  作者：Derek R. Boyd、Peter B. Coulter、Narain D. Sharma、W.Brian Jennings、Valerie E. Wilson

  DOI：10.1016/s0040-4039(00)98582-4

  日期：1985.1
• Regioselectivity of the 1,3-dipolar cycloaddition of fluorinated fluoren-9-iminium ylides to heteroelement-containing dipolarophiles: Experimental and quantum-chemical study
  作者：M. S. Novikov、A. F. Khlebnikov、M. A. Egarmin、M. V. Shevchenko、V. A. Khlebnikov、R. R. Kostikov、D. Vidovic

  DOI：10.1134/s1070428006120086

  日期：2006.12

  N-Substituted 9H-fluoren-9-imines react with difluorocarbene to give the corresponding iminium ylides whose further transformations in the absence of active dipolarophiles depend on the substituent at the nitrogen atom and reaction conditions. N-Ethyl-, N-benzyl-, and N-(2-phenylethyl)-9H-fluoren-9-imines are thus converted in low yield into the formal cyclodimerization products and/or 9H-fluorene-9-carboxamides. N-Methyl-substituted fluoreniminium ylide readily adds at the C=N bond of initial N-(9H-fluoren-9-ylidene)methanamine with formation of spiro-fused imidazolidine derivative; in the presence of fluorenone, acetaldehyde, or benzaldehyde, addition at the C=O group of the dipolarophile occurs to give the corresponding oxazolidine derivatives. The regioselectivity of the cycloaddition of iminium ylides having a fluorene fragment at a double carbon-heteroelement bond can be described by quantum-chemical calculations in terms of the density functional theory (DFT; local hard and soft acids and bases concept): the cycloaddition leads preferentially to the 2,2-difluoro-substituted adduct.
• BOYD, D. R.;COULTER, P. B.;SHARMA, NARAIN, D.;JENNINGS, W. B.;WILSON, V. +, TETRAHEDRON LETT., 1985, 26, N 13, 1673-1676
  作者：BOYD, D. R.、COULTER, P. B.、SHARMA, NARAIN, D.、JENNINGS, W. B.、WILSON, V. +

  DOI：——

  日期：——