6-Methoxy-2,2-dimethyl-1-indanyl acetate | 165072-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-Methoxy-2,2-dimethyl-1-indanyl acetate
• 英文别名: (6-Methoxy-2,2-dimethyl-1,3-dihydroinden-1-yl) acetate
• CAS: 165072-43-5
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: ONRFTGIVLNLHNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Methoxy-2,2-dimethyl-1-indanyl acetate 在 甲醇 作用下， 以60%的产率得到6-Methoxy-2,2-dimethyl-1-indanyl methyl ether
  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
• 作为产物：
  描述：

  乙酰氯 、 6-甲氧基-2,2-二甲基-1-茚满醇 在 吡啶 作用下， 以 苯 为溶剂， 生成 6-Methoxy-2,2-dimethyl-1-indanyl acetate
  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

文献信息

• The Photochemistry of Conformationally Rigid Benzylic Esters: 2,2-Dimethyl-1-indanyl Acetates and Pivalates
  作者：J. A. Pincock、P. J. Wedge

  DOI：10.1021/jo00118a024

  日期：1995.6

  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.