2-Phenyl-2-(1,1,3,3-tetramethyl-2-indanyliden)essigsaeure | 75501-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-Phenyl-2-(1,1,3,3-tetramethyl-2-indanyliden)essigsaeure
• 英文别名: 2-Phenyl-2-(1,1,3,3-tetramethylinden-2-ylidene)acetic acid
• CAS: 75501-37-0
• 化学式: C₂₁H₂₂O₂
• 分子量: 306.404
• InChiKey: APUYYESPGRHFTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,1,3,4-四甲基-2-茚酮 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 偶氮二异丁腈 、 溴 、 magnesium 、 1,2-二溴乙烷 作用下， 以 吡啶 、 四氯化碳 为溶剂， 反应 15.5h， 生成 2-Phenyl-2-(1,1,3,3-tetramethyl-2-indanyliden)essigsaeure
  参考文献：
  名称：

  Knorr, Rudolf; Lattke, Ernst; Raepple, Edith, Liebigs Annalen der Chemie, 1980, # 8, p. 1207 - 1215

  摘要：

  DOI：

文献信息

• Carbenoid Chain Reactions through Proton, Deuteron, or Bromine Transfer from Unactivated 1-Bromo-1-alkenes to Organolithium Compounds
  作者：Rudolf Knorr、Claudio Pires、Johannes Freudenreich

  DOI：10.1021/jo070623w

  日期：2007.8.1

  The deceptively simple vinylic substitution reactions Alk(2)CCABr + RLi -> Alk(2)CCAR + LiBr (A = H, D, or Br) occur via an alkylidenecarbenoid chain mechanism (three steps) without transition metal catalysis. 2-(Bromomethylidene)-1,1,3,3-tetramethylindan (Alk(2)CCH-Br, 2a) is deprotonated (step 1) by phenyllithium (PhLi) to give the Br,Li-alkylidenecarbenoid Alk(2)CCLi-Br (3). In the ensuing chain cycle, 3 and PhLi (step 2) form the observable alkenyllithium intermediate Alk(2)CCLiPh that characterizes the carbenoid mechanism in Et2O and is able to propagate the chain (step 3) through deprotonation of 2a, furnishing carbenoid 3 and the product Alk(2)CCHPh. The related 2-(dibromomethylidene)-1,1,3,3-tetramethylindan (Alk(2)CCBr(2), 2c) and methyllithium (MeLi) generate carbenoid 3 (step 1), which incorporates MeLi (step 2) to give Alk(2)CCLiCH(3), which reacts with 2c by bromine transfer producing Alk(2)CCBrCH(3) and carbenoid 3 (step 3). PhCCLi cannot carry out step 1, but MeLi can initiate (step 1) the carbenoid chain cycle (steps 2 and 3) of 2c with PhCCLi leading to Alk(2)CCBrCC-Ph. Reagent 2a may perform both proton and bromine transfer toward Alk(2)CCLiCH(3), feeding two coupled carbenoid chain processes in a ratio that depends on the solvent and on a primary kinetic H/D isotope effect.