9-benzyl-9-tert-butylfluorene | 85535-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-benzyl-9-tert-butylfluorene
• CAS: 85535-35-9
• 化学式: C₂₄H₂₄
• 分子量: 312.455
• InChiKey: FSRHBGUNFVTCRA-UHFFFAOYSA-N

物化性质

• 沸点：
  439.0±15.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.24
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  氯化苄 、 potassium salt of 9-tert-butylfluorene 在 tetrabutylammonium tetrafluoroborate 作用下， 以 二甲基亚砜 为溶剂， 生成 9-benzyl-9-tert-butylfluorene
  参考文献：
  名称：

  Systematic Ranking of Nucleophiles as Electron Donors.

  摘要：

  A systematic ranking of different nucleophiles (including enolates, phenolates, thiophenolates, hydroxide, cyanide) with respect to their ability to stabilise the transition state of substitution reactions has been carried out in acetonitrile and dimethyl sulfoxide. The method is based on a comparison of the rate constant, k(SUB), for the substitution reaction between a given nucleophile and benzyl chloride with the rate constant, ka(ET), for the corresponding electron transfer from an aromatic radical anion to benzyl chloride. The ratio k(SUB)/k(ET) expresses the rate enhancement due to electronic interaction in the transition state, Delta G(sta), of the substitution reaction. In this study, k(SUB)/k(ET) ratios between 5 and 10(31) were determined corresponding to Delta G(Sta)-values of 4-175 kJ mol(-1). These values cover substitution reactions going from outer-sphere electron transfer to S(N)2 with partial bond formation in the transition state. The k(SUB)/k(ET) values are round to be largest for nucleophiles such as OH- and CN- with very poor electron-donating abilities thigh oxidation potentials). When different. types of nucleophile with similar oxidation potentials are compared, a decrease in k(SUB)/k(ET) is observed going from sulfur- to carbon- and further to oxygen-centred nucleophiles. The ranking of nucleophiles in reactions involving electrophiles other than benzyl chloride is discussed with emphasis on steric hindrance and electronic effects.

  DOI：

  10.3891/acta.chem.scand.53-0938

文献信息

• Reactions of 9-substituted fluorenide carbanions with allyl chlorides by SN2 and SN2' mechanisms
  作者：Frederick G. Bordwell、Anthony H. Clemens、Jin Pei Cheng

  DOI：10.1021/ja00240a029

  日期：1987.3
• Role of single electron transfer in SN2-type substitution reactions of anions with alkyl halides
  作者：F. G. Bordwell、John A. Harrelson

  DOI：10.1021/jo00281a035

  日期：1989.9
• Steric and electronic effects in SN2 reactions of 9-substituted fluorenyl and .alpha.-cyano carbanions with benzyl chloride in dimethyl sulfoxide solution
  作者：Frederick G. Bordwell、David L. Hughes

  DOI：10.1021/jo00161a015

  日期：1983.7
• Direct relationship between nucleophilicity and basicity in SN2 reactions of fluorenyl anions with benzyl chloride in dimethyl sulfoxide solution
  作者：Frederick G. Bordwell、David L. Hughes

  DOI：10.1021/jo01304a035

  日期：1980.8
• BORDWELL F. G.; HUGHES D. L., J. ORG. CHEM., 1980, 45, NO 16, 3314-3320
  作者：BORDWELL F. G.、 HUGHES D. L.

  DOI：——

  日期：——