2-nitrobenzyl bromoacetate | 159538-04-2

• 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: 2-nitrobenzyl bromoacetate
• 英文别名: (2-Nitrophenyl)methyl 2-bromoacetate
• CAS: 159538-04-2
• 化学式: C₉H₈BrNO₄
• 分子量: 274.071
• InChiKey: FYIWBFGOVUHYCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-nitrobenzyl bromoacetate 在 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 2-nitrobenzyl penta-2,3-dienoate
  参考文献：
  名称：

  区域和立体选择性铜（II）催化的水中活化丙二烯的氢化硅烷化：获得乙烯基硅烷

  摘要：

  通过使用催化量的铜（II），4-甲基吡啶和二甲基苯基甲硅烷基萘烷硼烷，一系列的脲基甲酸酯以良好至极佳的收率和高（E）选择性被甲硅烷基化在β碳上。温和有效的甲硅烷基化方法是在水中在大气条件下进行的，以提供乙烯基硅烷。

  DOI：

  10.1021/acs.orglett.6b00981
• 作为产物：
  描述：

  邻硝基苯甲醇 、 溴乙酸 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以89%的产率得到2-nitrobenzyl bromoacetate
  参考文献：
  名称：

  Engineering Buffering and Hydrolytic or Photolabile Charge Shifting in a Polycarboxybetaine Ester Gene Delivery Platform

  摘要：

  Polycarboxybetaine esters (PCB-esters) can condense plasmid DNA into nanosized polyplexes for highly effective gene delivery with low toxicity. The design and characterization of tertiary CB-ester monomers and PCB-ester polymers are presented here to study the effects of molecular variation on functions important to nonviral gene transfer. Both buffering capacity and charge-shifting behavior can be tuned by modifying the distance between the charged groups and the ester size or type. A carbon spacer length (CSL) of one was found to bring the pK(a) of the tertiary amine into the optimal range for proton buffering. Ester hydrolytic degradation switches this polymer from cationic (DNA binding) to zwitterionic (DNA releasing) form while conferring nontoxicity. To allow rapid and externally controlled degradation, the effect of this charge-switching behavior on DNA release from polyplexes was directly studied with a novel photolabile PCB-nitrobenzyl ester (PCB-NBE). Photoinitiated ester degradation precipitated the rapid release of 72 +/- 5% of complexed DNA from PCB-NBE polyplexes. These insights reveal the key parameters important for the PCB-ester platform and the significance of charge switching to an effective and nontoxic nonviral gene delivery platform.

  DOI：

  10.1021/bm400221r

文献信息

• Process for preparing carbapenem compounds
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0679652A1

  公开（公告）日：1995-11-02

  Novel and effective process for preparing a carbapenem compound of the formula (III): wherein R₁ and R₂ are each H or lower alkyl, R₃ is lower alkyl, R₄ is protecting group, L is substituted or unsubstituted arylsulfonyloxy, lower alkanesulfonyloxy, halogeno-lower alkanesulfonyloxy, di-lower alkylphosphoryloxy, etc., and X is H or protected hydroxy, which comprises reacting β-lactam compound (I) with acetic acid ester derivative (II), in the presence of base, followed by treating the product with active esterifying agent for hydroxy group, said compound (III) being useful as intermediate for 1β-alkylcarbapenem compound having antibacterial activity.

  制备式（III）碳青霉烯类化合物的新颖有效的工艺： 其中 R₁ 和 R₂ 均为 H 或低级烷基，R₃ 为低级烷基，R₄ 为保护基，L 为取代或未取代的芳基磺酰氧基、低级烷基磺酰氧基、卤代低级烷基磺酰氧基、二低级烷基磷酰氧基等、和 X 是 H 或受保护的羟基，其中包括在碱存在下使β-内酰胺化合物（I）与乙酸酯衍生物（II）反应，然后用活性酯化剂处理羟基产物，所述化合物（III）可用作具有抗菌活性的 1β- 烷基碳青霉烯化合物的中间体。
• US5578722A
  申请人：——

  公开号：US5578722A

  公开（公告）日：1996-11-26
• Regio- and Stereoselective Copper(II)-Catalyzed Hydrosilylation of Activated Allenes in Water: Access to Vinylsilanes
  作者：Srinath Pashikanti、Joseph A. Calderone、Matthew K. Nguyen、Christopher D. Sibley、Webster L. Santos

  DOI：10.1021/acs.orglett.6b00981

  日期：2016.5.20

  By using catalytic amounts of copper(II), 4-picoline, and dimethylphenylsilylpinacol borane, a series of allenoates were silylated on the β carbon in good to excellent yields and high (E)-selectivity. The mild and efficient silylation method is conducted in water under atmospheric conditions to afford vinylsilanes.

  通过使用催化量的铜（II），4-甲基吡啶和二甲基苯基甲硅烷基萘烷硼烷，一系列的脲基甲酸酯以良好至极佳的收率和高（E）选择性被甲硅烷基化在β碳上。温和有效的甲硅烷基化方法是在水中在大气条件下进行的，以提供乙烯基硅烷。
• Engineering Buffering and Hydrolytic or Photolabile Charge Shifting in a Polycarboxybetaine Ester Gene Delivery Platform
  作者：Andrew Sinclair、Tao Bai、Louisa R. Carr、Jean-Rene Ella-Menye、Lei Zhang、Shaoyi Jiang

  DOI：10.1021/bm400221r

  日期：2013.5.13

  Polycarboxybetaine esters (PCB-esters) can condense plasmid DNA into nanosized polyplexes for highly effective gene delivery with low toxicity. The design and characterization of tertiary CB-ester monomers and PCB-ester polymers are presented here to study the effects of molecular variation on functions important to nonviral gene transfer. Both buffering capacity and charge-shifting behavior can be tuned by modifying the distance between the charged groups and the ester size or type. A carbon spacer length (CSL) of one was found to bring the pK(a) of the tertiary amine into the optimal range for proton buffering. Ester hydrolytic degradation switches this polymer from cationic (DNA binding) to zwitterionic (DNA releasing) form while conferring nontoxicity. To allow rapid and externally controlled degradation, the effect of this charge-switching behavior on DNA release from polyplexes was directly studied with a novel photolabile PCB-nitrobenzyl ester (PCB-NBE). Photoinitiated ester degradation precipitated the rapid release of 72 +/- 5% of complexed DNA from PCB-NBE polyplexes. These insights reveal the key parameters important for the PCB-ester platform and the significance of charge switching to an effective and nontoxic nonviral gene delivery platform.