1-Indanyl pivalate | 165072-66-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1-Indanyl pivalate
• 英文别名: 2,3-dihydro-1H-inden-1-yl 2,2-dimethylpropanoate
• CAS: 165072-66-2
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: PJESZKMVKBRKCT-UHFFFAOYSA-N

物化性质

• 沸点：
  295.2±19.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Indanyl pivalate 在 R,R-Jacobsen's catalyst 、 亚碘酰苯 、 silver fluoride 、 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 以51%的产率得到C₁₄H₁₇FO₂
  参考文献：
  名称：

  氟离子对锰催化的氧化型苯甲酰CH的氟化反应

  摘要：

  描述了一种有效的苄基CH键选择性氟化的方案。该方法由锰塞伦络合物催化，并使用亲核氟源，例如三乙胺三氟化氢和KF。反应速率足够高（30分钟），可允许将18 F氟化物源用于PET成像应用。

  DOI：

  10.1002/anie.201301097
• 作为产物：
  描述：

  2,3-二氢-1H-茚-1-醇 、 三甲基乙酰氯 在 吡啶 作用下， 以 苯 为溶剂， 生成 1-Indanyl pivalate
  参考文献：
  名称：

  The Photochemistry of Conformationally Rigid Benzylic Esters: 2,2-Dimethyl-1-indanyl Acetates and Pivalates

  摘要：

  The photochemistry, in methanol, of substituted 2,2-dimethyl-1-indanyl acetates 9a-c and pivalates 10a-c has been studied. In agreement with previous studies on benzylic esters, the results show that the substituents change the yield of products derived from the ion pair. The mechanistic conclusion reached is that the substituents change the oxidation potential of the indanyl radicals and thus the rate constant of electron transfer for converting the radical pair to the ion pair. The results also reveal two other substituent effects. First, substituents can increase the overall efficiency of the photoreaction by enhancing homolytic cleavage, The second effect is conformational. In compounds where the bond that is cleaving is conformationally mobile, such as the C-O bond in benzylic esters, substituents on the ring can change the population of the reactive conformer and thus the overall efficiency of the reaction. For the indanyl acetate esters, the difference in excited-state reaction rate between the m- and p-methoxy substituted ester is 15:1. For the m- and p-methoxy substituted benzyl acetates, this difference in reaction rate is 48:1. The larger difference in reaction rate for the conformationally mobile benzylic esters is attributed to a higher population of the unreactive conformer for the p-methoxy substituted ester.

  DOI：

  10.1021/jo00118a024