6-amino-6-methylpentafulvene | 694-74-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-amino-6-methylpentafulvene
• 英文别名: 6-amino-6-methylfulvene；1-cyclopenta-2,4-dien-1-ylideneethanamine
• CAS: 694-74-6
• 化学式: C₇H₉N
• 分子量: 107.155
• InChiKey: NQMAZILNWHLNBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-amino-6-methylpentafulvene 、 (S)-2-phthalimidopropionyl chloride 在 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以53%的产率得到rac-6-amino-6-methyl-2-(N-phthaloylalaninyl)pentafulvene
  参考文献：
  名称：

  Structural Features of Primary 6-Aminopentafulvenes and Some of Their Derivatives

  摘要：

  Starting from 6-amino-6-methylpentafulvene (2) 'ortho"-C-acylation or N-acylation can be achieved selectively. Treatment of 2 with phthaloyl-protected amino acid chlorides derived from alanine (3a) or valine (3b) leads exclusively to the formation of the "ortho"-C-acylated derivatives 4, isolated as racemates. Optically active N-acylated products 7 were prepared by coupling 5, obtained by NH deprotonation of 2, with the 1-hydroxybenzotriazole (HOBt) active-esters of alanine (6a), valine (6b), or leucine (6c) bearing benzylprotected amino groups, Complexes 2, 4a, 4b, and 7a were characterized by X-ray diffraction. Electron-withdrawing groups attached at the "ortho" ring position lead to a shortening of the external C6-N bond, whereas electron-withdrawing groups bound to the nitrogen atom lead to an elongation of the C6-N bond, compared to the parent system 2.

  DOI：

  10.1002/1099-0690(200109)2001:18<3531::aid-ejoc3531>3.0.co;2-9
• 作为产物：
  描述：

  6-methyl-6-dimethylaminofulvene 在 ammonium hydroxide 作用下， 生成 6-amino-6-methylpentafulvene
  参考文献：
  名称：

  Hafner,K. et al., Justus Liebigs Annalen der Chemie, 1964, vol. 678, p. 39 - 53

  摘要：

  DOI：

文献信息

• [DE] ÜBERGANGSMETALLVERBINDUNG<br/>[EN] TRANSITION METAL COMPOUND<br/>[FR] COMPOSE DE METAL DE TRANSITION
  申请人：TARGOR GMBH

  公开号：WO1999015536A1

  公开（公告）日：1999-04-01

  (DE) Übergangsmetallverbindung der Formel (I), worin L, m, M, X, n, R1, R2 und p die in der Beschreibung gegebene Bedeutung haben.(EN) The invention relates to a transition metal compound of formula (I), wherein L, m, M, X, n, R1, R2 and p have the meaning cited in the description.(FR) L'invention concerne un composé de métal de transition de formule (I), dans laquelle L, m, M, X, n, R1, R2 et p ont la signification mentionnée dans la description.

  (DE) 含 Transitionmetall化合物的化学式(I)，其中 L, m, M, X, n, R1, R2 和 p 分别表示描述中给出的含义。 (EN) The invention relates to a transition metal compound of formula (I), wherein L, m, M, X, n, R1, R2 and p have the significance cited in the description. (_FR) L'invention concerne un composé de métal de transition de formule (I), dans laquelle L, m, M, X, n, R1, R2 et p ont la signification mentionnée dans la description. 翻译后的中文文本： (DE) 含 Transitionmetall化合物的化学式(I)，其中 L, m, M, X, n, R1, R2 和 p 分别表示描述中给出的含义。 (EN) 该发明涉及一种含 Transitionmetall化合物的化学式(I)，其中 L, m, M, X, n, R1, R2 和 p 的含义如描述中所指出的。
• Hafner,K. et al., Justus Liebigs Annalen der Chemie, 1964, vol. 678, p. 39 - 53
  作者：Hafner,K. et al.

  DOI：——

  日期：——
• Reactions of Functional Groups at the Periphery of Group 4 Metallocene Frameworks: Selective Formation of a Cp-Bonded Azaboretidine Derivative by a Hydroboration Route
  作者：Doris Kunz、Gerhard Erker、Roland Fröhlich、Gerald Kehr

  DOI：10.1002/(sici)1099-0682(200003)2000:3<409::aid-ejic409>3.0.co;2-6

  日期：2000.3
• Structural Features of Primary 6-Aminopentafulvenes and Some of Their Derivatives
  作者：Doris Kunz、Roland Fröhlich、Gerhard Erker

  DOI：10.1002/1099-0690(200109)2001:18<3531::aid-ejoc3531>3.0.co;2-9

  日期：2001.9

  Starting from 6-amino-6-methylpentafulvene (2) 'ortho"-C-acylation or N-acylation can be achieved selectively. Treatment of 2 with phthaloyl-protected amino acid chlorides derived from alanine (3a) or valine (3b) leads exclusively to the formation of the "ortho"-C-acylated derivatives 4, isolated as racemates. Optically active N-acylated products 7 were prepared by coupling 5, obtained by NH deprotonation of 2, with the 1-hydroxybenzotriazole (HOBt) active-esters of alanine (6a), valine (6b), or leucine (6c) bearing benzylprotected amino groups, Complexes 2, 4a, 4b, and 7a were characterized by X-ray diffraction. Electron-withdrawing groups attached at the "ortho" ring position lead to a shortening of the external C6-N bond, whereas electron-withdrawing groups bound to the nitrogen atom lead to an elongation of the C6-N bond, compared to the parent system 2.
• Formation of a Constrained-Geometry Ziegler Catalyst System Containing a C1 Instead of the Usual Si1 Connection Between the Cyclopentadienyl and Amido Ligand Components
  作者：Lothar Duda、Gerhard Erker、Roland Fröhlich、Frank Zippel

  DOI：10.1002/(sici)1099-0682(199808)1998:8<1153::aid-ejic1153>3.0.co;2-r

  日期：1998.8