3,4-diethylnylmethylbenzoate | 302346-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-diethylnylmethylbenzoate
• 英文别名: methyl 3,4-diethynylbenzoate
• CAS: 302346-42-5
• 化学式: C₁₂H₈O₂
• 分子量: 184.194
• InChiKey: WRDOIKOMAVRCCC-UHFFFAOYSA-N

物化性质

• 沸点：
  300.9±37.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  3,4-diethylnylmethylbenzoate 在 1,2-cyclohexadiene 作用下， 以 氯苯 为溶剂， 以78%的产率得到2-萘甲酸甲酯
  参考文献：
  名称：

  Linear free energy relationships in the Bergman cyclization of 4-substituted-1,2-diethynylbenzenes

  摘要：

  A series of 4-substituted- 1,2-diethylnylbenzenes were prepared (1a-f) and subjected to Bergman cyclization. Bulk cyclization proceeded to produce the corresponding 2-substituted naphthalenes (2a-f) in good yields (59-78%). Kinetic experiments show a linear free energy relationship between the cyclization rate and the Hammett sigma(m) substituent coefficient and the Swain-Lupton field and resonance parameters. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01181-3
• 作为产物：
  描述：

  原儿茶酸 在 copper(l) iodide 、 四(三苯基膦)钯 、 sodium methylate 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 170.25h， 生成 3,4-diethylnylmethylbenzoate
  参考文献：
  名称：

  AFM-Induced Amine Deprotection:  Triggering Localized Bond Cleavage by Application of Tip/Substrate Voltage Bias for the Surface Self-Assembly of Nanosized Dendritic Objects

  摘要：

  An alpha,alpha-dimethyl-3,5-dimethoxybenzyloxycarbonyl (DDZ)-protected amine monolayer can be selectively deprotected by the application of a voltage bias from a conducting AFM tip to afford localized nanoscale patterns that can be visualized by self-assembly of dendritic molecular objects with terminal carboxylic acid groups and different aspect ratios.

  DOI：

  10.1021/ja047774q

文献信息

• AFM-Induced Amine Deprotection:  Triggering Localized Bond Cleavage by Application of Tip/Substrate Voltage Bias for the Surface Self-Assembly of Nanosized Dendritic Objects
  作者：Zachary M. Fresco、Itai Suez、Scott A. Backer、Jean M. J. Fréchet

  DOI：10.1021/ja047774q

  日期：2004.7.14

  An alpha,alpha-dimethyl-3,5-dimethoxybenzyloxycarbonyl (DDZ)-protected amine monolayer can be selectively deprotected by the application of a voltage bias from a conducting AFM tip to afford localized nanoscale patterns that can be visualized by self-assembly of dendritic molecular objects with terminal carboxylic acid groups and different aspect ratios.
• Linear free energy relationships in the Bergman cyclization of 4-substituted-1,2-diethynylbenzenes
  作者：Nakyen Choy、Chang-Sik Kim、Cynthia Ballestero、Leanne Artigas、Christian Diez、Frank Lichtenberger、Jed Shapiro、K.C Russell

  DOI：10.1016/s0040-4039(00)01181-3

  日期：2000.9

  A series of 4-substituted- 1,2-diethylnylbenzenes were prepared (1a-f) and subjected to Bergman cyclization. Bulk cyclization proceeded to produce the corresponding 2-substituted naphthalenes (2a-f) in good yields (59-78%). Kinetic experiments show a linear free energy relationship between the cyclization rate and the Hammett sigma(m) substituent coefficient and the Swain-Lupton field and resonance parameters. (C) 2000 Elsevier Science Ltd. All rights reserved.