4-bromo-N,N-bis(2-chloroethyl)aniline | 13165-32-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-bromo-N,N-bis(2-chloroethyl)aniline
• 英文别名: N,N-Bis-(2-chlorethyl)-4-bromanilin；4-Bromo-N,N-bis(2-chloroethyl)anilinato
• CAS: 13165-32-7
• 化学式: C₁₀H₁₂BrCl₂N
• 分子量: 297.022
• InChiKey: PNYUBOYGGJQKJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-N,N-bis(2-chloroethyl)aniline 在 仲丁基锂 、 氧气 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 1.5h， 以35%的产率得到N,N-双(2-氯乙基)-4-羟基苯胺
  参考文献：
  名称：

  [EN] METHODS FOR INDUCING BIOORTHOGONAL REACTIVITY
  [FR] PROCÉDÉS POUR INDUIRE UNE RÉACTIVITÉ BIO-ORTHOGONALE

  摘要：

  将二氢四氮唑1催化转化为四氮唑2的方法，其中二氢四氮唑1上的一个R基团是取代或未取代的芳基、杂环芳基、烷基、烯基、炔基、羰基或含杂原子的基团，另一个R基团选自H和取代或未取代的芳基、杂环芳基、烷基、烯基、炔基、羰基或含杂原子的基团；其中该方法包括在反应介质中在催化剂和化学计量氧化剂的存在下氧化二氢四氮唑1。

  公开号：

  WO2017106427A1
• 作为产物：
  描述：

  N,N-双(2-氯乙基)苯胺 在 tetra-N-butylammonium tribromide 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以65.8%的产率得到4-bromo-N,N-bis(2-chloroethyl)aniline
  参考文献：
  名称：

  4′ DIPHENYLPHOSPHINO AND BROMO DERIVATIVES OF 10-PHENYL-1,4,7-TRITHIA-10-AZA-CYCLODODECANE 4-R- C₆H₄ N(CH₂CH₂S)₂CH₂CH₂SCH₂CH₂

  摘要：

  4-Br-C6H4N(CH2CH2S)(2)CH2CH2SCH2CH2 and 4-Ph2P-C6H4N(CH2CH2S)(2)CH2CH2SCH2CH2 have been synthesized and characterized. The former cyclododcane has been obtained from the reaction between 4-BrC6H4N(CH2CH2Cl)(2) and S(CH2CH2SH)(2) in N,N-dimethylformamide containing Cs2CO3. The latter has been obtained from the former by way of a low temperature lithiumbromine exchange reaction (butyllithium) that provided the carbanion which was subsequently reacted with chlorodiphenylphosphine. In regard to characterization, X-ray methods have been used to study the former (P2(1), a = 8.356(3) Angstrom, b = 12.325(5) Angstrom, c = 16.012 (7), beta = 100.81, Z = 4), and two crystallographically independent molecules were found. In both molecules, the nitrogen atoms are nearly planar with short N-C(sp(2)) bond lengths, and, second, the sulfur atoms are in exodenate positions. For the phosphine, a P-31 signal was observed at -7.1 ppm, and this peak position was considered to be indicative of a structure involving a planar nitrogen atom.

  DOI：

  10.1080/10426509708043504

文献信息

• ANTI-CANCER AGENTS
  申请人：Peng Xiaohua

  公开号：US20130045949A1

  公开（公告）日：2013-02-21

  Described herein are compounds that may be selectively activated to produce active anti-cancer agents in tumor cells. Also disclosed are pharmaceutical compositions comprising the compounds, and methods of treating cancer using the compounds.

  本文描述了一些化合物，这些化合物可以被选择性地激活，以在肿瘤细胞中产生活性抗癌剂。还公开了包括这些化合物的药物组合物，以及使用这些化合物治疗癌症的方法。
• Twofold photoswitching of NIR fluorescence and EPR based on the PMI–N–HABI for optical nanoimaging of electrospun polymer nanowires
  作者：Wen-Liang Gong、Zu-Jing Xiong、Bo Xin、Hong Yin、Jia-Shun Duan、Jie Yan、Tao Chen、Qiong-Xin Hua、Bin Hu、Zhen-Li Huang、Ming-Qiang Zhu

  DOI：10.1039/c6tc00542j

  日期：——

  time (τ1/2) of 1.3 s in toluene at 297 K. The radical nature of the colored species is verified by EPR measurements. The emission of the perylenemonoimide could be reversibly quenched by the photo-induced radicals through the Forster resonance energy transfer (FRET) mechanism. The fluorescence-switching dye is applied to the optical nanoimaging of polymer nanowires prepared using the typical electrospinning

  在本文中，我们报告了基于per单酰亚胺-六芳基联咪唑二聚体（PMI–N–HABI）的荧光分子开关的设计和合成，该开关不仅表现出光可开关的近红外（NIR）荧光，而且表现出光可开关的电子顺磁共振（EPR）是由光诱导的双自由基引起的。由于D–π–A分子结构，PMI–N–HABI的发射随溶剂极性的不同而变化，在二氯甲烷中显示出强的NIR发射（715 nm），荧光量子产率高达0.29。两个咪唑基团之间的C–N键的光诱导裂解在紫外线照射下有效地产生了两个自由基，并且有色物质由于两个分子内TPIR在几秒钟内的碰撞而自发地恢复了初始状态，297 K在甲苯中1.3 s的τ1 /2）。有色物质的自由基性质通过EPR测量得到证实。通过Forster共振能量转移（FRET）机理，光诱导的自由基可逆地猝灭per一酰亚胺的发射。将荧光转换染料应用于使用典型电纺丝方法制备的聚合物纳米线的光学纳米成像中。约160nm的平
• 一种合成苯丁酸氮芥的方法
  申请人：南京工业大学

  公开号：CN113121373B

  公开（公告）日：2022-06-24

  本发明公开了一种合成苯丁酸氮芥的方法，涉及有机化学技术领域，包括以下步骤：S1、将配比含量为10.83％：10.83％－32.50％：0.22％－2.17％：0.43％－2.17％：10.83％－54.17％：10.83％－54.17％的4‑溴‑N，N‑双(2‑氯乙基)苯胺、N‑(喹啉‑8‑基)丁‑3‑烯酰胺、氯化钯、三正丁基膦四氟硼酸盐、碳酸钾、苯甲酸所制成的混合物和二甲基亚砜按摩尔体积比0.1mmol：2mL加入到反应容器中混匀；S2、将反应容器置于135～145℃油浴中剧烈搅拌反应24小时。本发明通过偶联反应，设计8‑氨基喹啉作为可离去基团的化合物来控制反应中的区域和化学选择性，有效解决了现有苯丁酸氮芥的合成过程中步骤过多的问题，且本发明具有反应区域选择性及得率高、反应条件温和、反应及后处理纯化过程简单的特点。
• Methods for inducing bioorthogonal reactivity
  申请人：Fox Joseph

  公开号：US10875840B2

  公开（公告）日：2020-12-29

  A method for catalytically converting a dihydrotetrazine 1 into a tetrazine 2, wherein one R group on the dihydrotetrazine 1 is a substituted or unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl, or heteroatom-containing group, and the other R group is selected from the group consisting of H and substituted or unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl,- or heteroatom-containing groups; 1, 2 wherein the method comprises oxidizing dihydrotetrazine 1 in a reaction medium in the presence of a catalyst and a stoichiometric oxidant.

  一种催化二氢四嗪1转化为四嗪2的方法，其中二氢四嗪1上的一个R基团是取代或未取代的芳基、杂芳基、烷基、烯基、炔基、羰基或含杂原子的基团，另一个R基团选自由H和取代或未取代的芳基、杂芳基、烷基、烯基、炔基、羰基或含杂原子的基团组成的组；1, 2 其中该方法包括在催化剂和定量氧化剂存在下，在反应介质中氧化二氢四嗪 1。
• Reactive Oxygen Species (ROS) Inducible DNA Cross-Linking Agents and Their Effect on Cancer Cells and Normal Lymphocytes
  作者：Wenbing Chen、Kumudha Balakrishnan、Yunyan Kuang、Yanyan Han、Min Fu、Varsha Gandhi、Xiaohua Peng

  DOI：10.1021/jm401349g

  日期：2014.6.12

  Reducing host toxicity is one of the main challenges of cancer chemotherapy. Many tumor cells contain high levels of ROS that make them distinctively different from normal cells. We report a series of ROS-activated aromatic nitrogen mustards that selectively kill chronic lymphocytic leukemia (CLL) over normal lymphocytes. These agents showed powerful DNA cross-linking abilities when coupled with H2O2, one of the most common ROS in cancer cells, whereas little DNA cross-linking was detected without H2O2. Consistent with chemistry observation, in vitro cytotoxicity assay demonstrated that these agents induced 40-80% apoptosis in primary leukemic lymphocytes isolated from CLL patients but less than 25% cell death to normal lymphocytes from healthy donors. The IC50 for the most potent compound (2) was similar to 5 mu M in CLL cells, while the IC50 was not achieved in normal lymphocytes. Collectively, these data provide utility and selectivity of these agents that will inspire further and effective applications.