4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl 4-formylphenylcarbamate | 1349832-91-2

• 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: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl 4-formylphenylcarbamate
• 英文别名: [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl N-(4-formylphenyl)carbamate
• CAS: 1349832-91-2
• 化学式: C₂₁H₂₄BNO₅
• 分子量: 381.236
• InChiKey: XXTPLGPFJPNNEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  40 °C
• 沸点：
  503.7±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl 4-formylphenylcarbamate 在 三氟甲磺酸三甲基硅酯 、 过氧化脲素 作用下， 以 water-d2 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 对羟基苯甲醇
  参考文献：
  名称：

  A Structurally Simple Self-Immolative Reagent That Provides Three Distinct, Simultaneous Responses per Detection Event

  摘要：

  A general design is presented for a stimulus-responsive small molecule that is capable of responding to a specific applied chemical or physical signal by releasing two different types of pendant small molecules and a colorimetric indicator simultaneously. A key aspect of this design is the ease with which these reagents are prepared: typically, only four synthetic steps are required. Moreover, the modular construction strategy provides access to stimuli-responsive reagents that are capable of (i) responding to a variety of applied signals and (ii) releasing a number of different small molecules that contain primary alcohols, secondary alcohols, or phenols. These stimuli-responsive reagents are stable under physiological conditions (neither hydrolysis nor thermal degradation of the reagent occurs in significant quantity), and when they are exposed to the appropriate applied signal, they release both pendant small molecules and the colorimetric indicator completely within hours. Finally, unlike other functional groups, such as carbonates, that are used to connect alcohol-bearing molecules to controlled-release reagents, the linkage described in this article increases in hydrolytic stability (rather than decreases) as the plc of the pendant alcohol decreases.

  DOI：

  10.1021/jo2018763
• 作为产物：
  描述：

  4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl 4-(dimethoxymethyl)phenylcarbamate 以 water-d2 、 氘代乙腈 为溶剂， 反应 6.0h， 以100%的产率得到4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl 4-formylphenylcarbamate
  参考文献：
  名称：

  A Structurally Simple Self-Immolative Reagent That Provides Three Distinct, Simultaneous Responses per Detection Event

  摘要：

  A general design is presented for a stimulus-responsive small molecule that is capable of responding to a specific applied chemical or physical signal by releasing two different types of pendant small molecules and a colorimetric indicator simultaneously. A key aspect of this design is the ease with which these reagents are prepared: typically, only four synthetic steps are required. Moreover, the modular construction strategy provides access to stimuli-responsive reagents that are capable of (i) responding to a variety of applied signals and (ii) releasing a number of different small molecules that contain primary alcohols, secondary alcohols, or phenols. These stimuli-responsive reagents are stable under physiological conditions (neither hydrolysis nor thermal degradation of the reagent occurs in significant quantity), and when they are exposed to the appropriate applied signal, they release both pendant small molecules and the colorimetric indicator completely within hours. Finally, unlike other functional groups, such as carbonates, that are used to connect alcohol-bearing molecules to controlled-release reagents, the linkage described in this article increases in hydrolytic stability (rather than decreases) as the plc of the pendant alcohol decreases.

  DOI：

  10.1021/jo2018763

文献信息

• A Structurally Simple Self-Immolative Reagent That Provides Three Distinct, Simultaneous Responses per Detection Event
  作者：Sean A. Nuñez、Kimy Yeung、Nicole S. Fox、Scott T. Phillips

  DOI：10.1021/jo2018763

  日期：2011.12.16

  A general design is presented for a stimulus-responsive small molecule that is capable of responding to a specific applied chemical or physical signal by releasing two different types of pendant small molecules and a colorimetric indicator simultaneously. A key aspect of this design is the ease with which these reagents are prepared: typically, only four synthetic steps are required. Moreover, the modular construction strategy provides access to stimuli-responsive reagents that are capable of (i) responding to a variety of applied signals and (ii) releasing a number of different small molecules that contain primary alcohols, secondary alcohols, or phenols. These stimuli-responsive reagents are stable under physiological conditions (neither hydrolysis nor thermal degradation of the reagent occurs in significant quantity), and when they are exposed to the appropriate applied signal, they release both pendant small molecules and the colorimetric indicator completely within hours. Finally, unlike other functional groups, such as carbonates, that are used to connect alcohol-bearing molecules to controlled-release reagents, the linkage described in this article increases in hydrolytic stability (rather than decreases) as the plc of the pendant alcohol decreases.