9-(2-(dimethylamino)ethyl)fluorene | 57722-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-(2-(dimethylamino)ethyl)fluorene
• 英文别名: [9-(2-dimethylamino)ethyl]fluorene；(2-fluoren-9-yl-ethyl)-dimethyl-amine；(2-Fluoren-9-yl-aethyl)-dimethyl-amin；2-Dimethylaminoethyl-fluoren；2-(9H-fluoren-9-yl)-N,N-dimethylethanamine
• CAS: 57722-08-4
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: QOPYDBARFANKDB-UHFFFAOYSA-N

物化性质

• 沸点：
  159-161 °C(Press: 2 Torr)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-(2-(dimethylamino)ethyl)fluorene 在 (三苯基甲基)-锂 作用下， 以 四氢呋喃 为溶剂， 生成 9-(2-(dimethylamino)ethyl)fluorenyllithium
  参考文献：
  名称：

  碳酸度。75.杂取代的侧基对碳负离子反应性的影响。9-取代芴在四氢呋喃中的动力学酸度。游离离子在离域碳负离子盐反应中的重要性

  摘要：

  取代基：甲氧基乙基-、二甲氨基乙基-、甲硫基乙基-、等正丁基-

  DOI：

  10.1021/ja00217a025
• 作为产物：
  描述：

  芴 在 sodium amide 、 甲苯 作用下， 生成 9-(2-(dimethylamino)ethyl)fluorene
  参考文献：
  名称：

  The Synthesis of Some Fluorene Derivatives¹

  摘要：

  DOI：

  10.1021/ja01613a058

文献信息

• Carbon acidity. 74. The effects of hetero-substituted pendant groups on carbanion reactivity. Solvent separated-contact ion pair equilibria and relative pKLi/THF's for 9-substituted fluorenyllithiums in tetrahydrofuran. The importance of internal chelation
  作者：Scott. Gronert、Andrew. Streitwieser

  DOI：10.1021/ja00217a024

  日期：1988.4

  Les substituants sont les groupes: methoxyethyl-, dimethylaminoethyl-, methylthioethyl-, butyl-, CH 3 OCH 2 CH 2 OCH 2 CH 2 -, H-

  取代基：甲氧基乙基-、二甲氨基乙基-、甲硫基乙基-、丁基-、CH 3 OCH 2 CH 2 OCH 2 CH 2 -、H-
• Ca‐Mediated Styrene Polymerization: Tacticity Control by Ligand Design
  作者：Dirk F.‐J. Piesik、Karin Häbe、Sjoerd Harder

  DOI：10.1002/ejic.200700802

  日期：2007.12

  for inversion at the chiral benzylic carbon atom [18.7(2)–19.2(2) kcal/mol]. Complex 4 does not initiate styrene polymerization, which underscores the importance of a free coordination site at calcium. Complexes 5–9 initiate styrene polymerization, and the syndiotacticity of the obtained polymers increases with the bulkiness of the substituents on the fluorenyl ligands. Syndiotacticities up to r = 95 %

  制备了具有修饰芴基配体的新型杂配苄基钙配合物，其中包括具有螯合二甲氨基取代基的配合物，[9-(2-Me2N-乙基)芴基][2-Me2N-α-Me3Si-苄基]Ca(4)，以及在芴基配体的 2 位和 7 位具有大量取代基的一系列配合物，如 tBu-、Ph(Me)2C-、Me(Ph)2C- 和 Me(4-tBuC6H4)2C-（配合物 5 到 9，分别）。4、[(2,7-tBu-9-Me3Si-芴基)(2-Me2N-苄基)Ca]2(5)和[2,7-Ph(Me)2C-9-Me3Si-芴基]的晶体结构[2-Me2N-α-Me3Si-苄基]Ca·THF (6) 表明芴基配体的修饰几乎不影响苄基配体的配位模式。此外，在溶液中，所有化合物都具有杂配性质，并且表明芴基修饰几乎不会影响手性苄基碳原子上的反转势垒[18.7(2)-19。2(2) 千卡/摩尔]。配合物 4 不会引发苯乙烯聚合，这强调了钙处自由配位点的重要性。配合物
• Bis-ammonium Salts. Derivatives of Fluorene, Carbazole and Phenothiazine
  作者：Chester J. Cavallito、Allan P. Gray、Ernest E. Spinner

  DOI：10.1021/ja01636a037

  日期：1954.4
• Aluminum Effects in the Syndiospecific Copolymerization of Styrene with Ethylene by Cationic Fluorenyl Scandium Alkyl Catalysts
  作者：Xiaofang Li、Xiaoying Wang、Xin Tong、Hongxia Zhang、Yuanyuan Chen、Ying Liu、Hui Liu、Xiaojie Wang、Masayoshi Nishiura、Huan He、Zhenguo Lin、Shaowen Zhang、Zhaomin Hou

  DOI：10.1021/om3011036

  日期：2013.3.11

  A series of half-sandwich fluorenyl (Flu') scandium dialkyl complexes Flu'Sc(CH2SiMe3)(2)(THF)(n) (1, Flu' = C13H9, n = 1; 2, Flu' = 2,7-(Bu2C13H7)-Bu-t, n = 1; 3, Flu' = 9-SiMe3C13H8, n = 1; 4, Flu' = 2,7-Bu-t(2)-9-SiMe3C13H6, n = 1; 5, Flu' = 9-CH2CH2NMe2C13H6, n = 0; 6, Flu' = 2,7-Bu-t(2)-9-CH2CH2NMe2C13H6, n = 0) have been synthesized and structurally characterized. In comparison with the well-known cyclopentadienyl-ligated scandium catalyst system [(C5Me4SiMe3)Sc-(CH2SiMe3)(2)(THF)]/[Ph3C][B(C6F5)(4)], the analogous combinations of the fluorenyl-ligated, THF-containing complexes 1-4 with [Ph3C] [B(C6F5)(4)] show relatively low activities, albeit with similar syndioselectivities for styrene polymerization and styrene-ethylene copolymerization. However, on treatment with 15 equiv of (AlBu3)-Bu-t, the 1-4/[Ph3C][B(C6F5)(4)] combinations show a dramatic increase in catalytic activity without changes in the stereoselectivity. In contrast, the combinations of complexes 5 and 6, which have an amino group attached to the fluorenyl ring and intramolecularly bonded to the metal center, exhibit very low activity, no matter whether or not All3u3 is present, affording syndiotactic polystyrenes with broad molecular weight distributions. The DFT calculations of the activation mechanism by using the representative catalysts suggest that Arl3u3 can capture the THF molecule from the catalyst precursors 1-4 at first,and then the new, THF-free cationic half-sandwich scandium active species [Flu'Sc(CH2SiMe3)][B(C6F5)(4)] with less steric hindrance around the metal center is generated in the presence of an activator such as [Ph3C][B(C6F5)(4)]. The DFT calculations on the syndioselectivity of styrene (co)polymerization catalyzed by [Flu'Sc(CH2SiMe3)][B(C6F5)(4)] have also been carried out, thus shedding new light on the mechanistic aspects of the (co)polymerization processes.
• Base-Catalyzed Alkylations with Alcohols. IV
  作者：STEPHEN S. HIRSCH、DONALD H. LORENZ、ERNEST I. BECKER

  DOI：10.1021/jo01106a003

  日期：1958.12