Methyl benzonorbornene-1-carboxylate | 31859-49-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl benzonorbornene-1-carboxylate
• 英文别名: Methyl tricyclo[6.2.1.02,7]undeca-2,4,6-triene-1-carboxylate
• CAS: 31859-49-1
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: MYJBORQRJQDDPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,6,7,8-Tetrachloro-3,4-dihydro-2H-1,4-methano-naphthalene-1-carboxylic acid 在 镍 氢氧化钾 作用下， 生成 Methyl benzonorbornene-1-carboxylate
  参考文献：
  名称：

  Benzonorbornene and derivatives. IV. Bridgehead and 1-carbinyl derivatives

  摘要：

  DOI：

  10.1021/jo00832a066

文献信息

• Spectroscopy and Photochemistry of Phenylacetic Acid Esters and Related Substrates. The Stereoelectronic Dependence of the Aryl/Carboxyl Bichromophore Interaction
  作者：Annette M. Kasper、John J. Nash、Harry Morrison

  DOI：10.1021/jo00089a025

  日期：1994.5

  The 254-nm-initiated Norrish Type II photofragmentation of the ethoxyethyl esters of a series of phenylacetic acids (1b-4b) has been studied in order to further elaborate the aryl/ester interaction that is photochemically and photophysically evident in these systems. The ethoxyethyl ester of benzonorbornene-1-carboxylic acid (5) has also been prepared and studied, as has a rigid tricyclic lactone (6) which places the chromophores in an optimal stereoelectronic relationship for interaction. The experimental work is accompanied by Hartree-Fock (HF), Natural Bond Orbital (NBO), and Configuration Interaction with Single Excitations (CIS) calculations on the methyl esters of phenylacetic acid (1a) and alpha-methoxyphenylacetic acid (4a). The calculations confirm extensive through-space (TS) and through-bond (TB) interactions between the aryl and ester pi* orbitals but fail to provide conformational or electronic arguments to explain the unusually high reactivity of the alpha-methoxy series.