1,2-bis(p-chlorobenzylamino)ethane | 58015-08-0

• 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: 1,2-bis(p-chlorobenzylamino)ethane
• 英文别名: N¹,N²-bis(4-chlorobenzyl)ethane-1,2-diamine；N,N'-bis(4-chlorobenzyl)ethylenediamine；N,N'-bis[(4-chlorophenyl)methyl]ethane-1,2-diamine
• CAS: 58015-08-0
• 化学式: C₁₆H₁₈Cl₂N₂
• 分子量: 309.238
• InChiKey: CYMQHJTXFPRIMG-UHFFFAOYSA-N

物化性质

• 沸点：
  174-176 °C(Press: 0.1 Torr)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-bis(p-chlorobenzylamino)ethane 生成 1,2-Bis-(N-acetyl-N-p-chlorbenzyl-amino)-aethan
  参考文献：
  名称：

  SINGH, SERJINDER;SHARMA, VIJAY, K.;GILL, SARBJEET;SAHOTA, RAVJIT, INDER, +, J. CHEM. SOC. PERKIN TRANS., 1985, N 3, 437-440

  摘要：

  DOI：
• 作为产物：
  描述：

  N1,N2-二[(4-氯苯基)亚甲基]-1,2-乙二胺 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 1,2-bis(p-chlorobenzylamino)ethane
  参考文献：
  名称：

  N,N'-二取代乙二胺选择性单烷基化的便捷“一锅法”反应

  摘要：

  摘要 研究了N,N'-二取代乙二胺I单烷基化“一锅法”制备N,N,N'-三取代乙二胺III的方法范围。它涉及化合物 I 与醛的缩合，然后在没有预先分离的情况下还原形成的咪唑烷 II。

  DOI：

  10.1081/scc-120023441

文献信息

• Heterocyclic derivative and pharmaceutical composition comprising the same
  申请人：Kai Hiroyuki

  公开号：US09212130B2

  公开（公告）日：2015-12-15

  The present invention provides novel compounds having a P2X3 and/or P2X2/3 receptor antagonistic effect. A pharmaceutical composition having a P2X3 and/or P2X2/3 receptor antagonistic effect comprising a compound of the formula (I): wherein ring A is substituted or unsubstituted 5 to 7-membered cycloalkane, substituted or unsubstituted 5 to 7-membered cycloalkene or the like; C is a carbon atom; —X— is —N(R16)— or the like; R16 is hydrogen, substituted or unsubstituted alkyl or the like; R7 is substituted or unsubstituted 5- or 6-membered heteroaryl, substituted or unsubstituted 6 to 10 membered aryl; Q1 and Q2 are each independently a carbon atom or a nitrogen atom; -L- is —O—, —S— or the like; R6 is substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl or the like; R2 is hydrogen, hydroxy or the like, or its pharmaceutically acceptable salt or a solvate thereof.

  本发明提供了具有P2X3和/或P2X2/3受体拮抗作用的新化合物。具有P2X3和/或P2X2/3受体拮抗作用的药物组合物包括式(I)的化合物：其中环A是取代或未取代的5至7成员环烷烃，取代或未取代的5至7成员环烯烃等；C是碳原子；-X-是-N(R16)-等；R16是氢、取代或未取代的烷基等；R7是取代或未取代的5-或6-成员杂芳基，取代或未取代的6至10成员芳基；Q1和Q2分别是碳原子或氮原子；-L-是-O-、-S-等；R6是取代或未取代的环烷基，取代或未取代的环烯基等；R2是氢、羟基等，或其药学上可接受的盐或溶剂化合物。
• Enantioselective Organocatalytic Synthesis of 2-Oxopiperazines from Aldehydes: Identification of the Elusive Epoxy Lactone Intermediate
  作者：Nikolaos Kaplaneris、Constantinos Spyropoulos、Maroula G. Kokotou、Christoforos G. Kokotos

  DOI：10.1021/acs.orglett.6b02699

  日期：2016.11.18

  organocatalytic linchpin catalysis approach was envisaged to convert simple aldehydes into enantioenriched 2-oxopiperazines. A four-step reaction sequence (chlorination, oxidation, substitution, and cyclization) was developed and led to different substitution patterns in high yields and selectivities. The reaction mechanism was studied, and the previously elusive epoxy lactone intermediate was identified by

  设想了一种有机催化的关键催化方法，将简单的醛转化为对映体富集的2-氧代哌嗪。开发了四步反应序列（氯化，氧化，取代和环化），并以高收率和选择性导致了不同的取代方式。研究了反应机理，并通过HRMS鉴定了以前难以捉摸的环氧内酯中间体。
• Synthesis, antimicrobial activity and structure–activity relationship study of N,N-dibenzyl-cyclohexane-1,2-diamine derivatives
  作者：Mukul Sharma、Penny Joshi、Nitin Kumar、Seema Joshi、Rajesh K. Rohilla、Nilanjan Roy、Diwan S. Rawat

  DOI：10.1016/j.ejmech.2010.11.027

  日期：2011.2

  We report herein synthesis and antimicrobial activity of a series of N,N-dibenzyl-cyclohexane-1,2-diamine derivatives. In order to study the structure–activity relationship of substituted dibenzyl-cyclohexane-1,2-diamine derivatives, 44 structurally diverse compounds were synthesized and tested against Gram-positive and Gram-negative bacterial strains. Among them, compounds 17-20, 26, 37, 38 were found

  我们在本文中报道了一系列N，N-二苄基-环己烷-1,2-二胺衍生物的合成和抗菌活性。为了研究取代的二苄基-环己烷-1，2-二胺衍生物的结构-活性关系，合成了44种结构多样的化合物，并针对革兰氏阳性和革兰氏阴性细菌菌株进行了测试。其中，化合物17-20，26，37，38被发现是比MIC值范围0.0005-0.032微克/毫升四环素和在哺乳动物红细胞不溶血高达1024微克/毫升，观察到更活跃。一些化合物还显示出对白念珠菌非常有希望的抗真菌活性，光滑念珠菌和Geotrichum念珠菌。
• Titanium isopropoxide complexes of a series of sterically demanding aryloxo based [N2O2]2− ligands as precatalysts for ethylene polymerization
  作者：Manas K. Panda、Sukhdeep Kaur、Annapureddy Rajasekhar Reddy、Mobin M. Shaikh、Ray J. Butcher、Virendrakumar Gupta、Prasenjit Ghosh

  DOI：10.1039/c0dt00407c

  日期：——

  Several titanium isopropoxide complexes [N,N′-bis(2-oxo-3-R1-5-R2-phenylmethyl)-N,N′-bis(methylene-p-R3-C6H4)-ethylenediamine]Ti(OiPr)2 [R1 = t-Bu, R2 = Me, R3 = H (1b); R1 = R2 = t-Bu, R3 = H, (2b); R1 = R2 = Cl, R3 = H, (3b), R1 = t-Bu, R2 = Me, R3 = Cl (4b); R1 = R2 = t-Bu, R3 = Cl, (5b); R1 = R2 = R3 = Cl, (6b)] supported over sterically demanding aryloxy based [N2O2]H2 ligands have been designed as precatalysts for the ethylene polymerization. Specifically, the 1b–6b complexes, when treated with methylaluminoxane (MAO) under 88 ± 0.5 psi of ethylene at 30 °C for 3 h, produced polyethylene polymers of high molecular weight (Mw = ca. 7.2–8.3 × 105 g mol−1) having broad molecular weight distribution (PDI = ca. 13.1–14.6). The 1b–6b complexes were conveniently synthesized from the direct reaction of the [N2O2]H2 ligands, 1a–6a, with Ti(OiPr)4 in 69–86% yield.

  几种异丙醇钛络合物[N,N²-双(2-氧代-3-R1-5-R2-苯甲基)-N,N²-双(亚甲基-p-R3-C6H4)-乙二胺]Ti(OiPr)2 [R1 = t-Bu，R2 = Me，R3 = H (1b)；R1 = R2 = t-Bu，R3 = H，(2b)；R1 = R2 = Cl, R3 = H, (3b), R1 = t-Bu, R2 = Me, R3 = Cl (4b); R1 = R2 = t-Bu, R3 = Cl, (5b); R1 = R2 = R3 = Cl, (6b)] 已被设计为乙烯聚合的前催化剂。具体来说，当 1bâ6b 复合物与甲基铝氧烷（MAO）在 88 ± 0.5 psi 的乙烯条件下于 30 °C 处理 3 小时后，可生成具有宽分子量分布（PDI = 约 13.1â14.6）的高分子量聚乙烯聚合物（Mw = 约 7.2â8.3 à 105 g molâ1）。1bâ6b配合物是由[N2O2]H2配体1aâ6a与Ti(OiPr)4直接反应合成的，产率为69.86%。
• Systematic research of H2dedpa derivatives as potent inhibitors of New Delhi Metallo-β-lactamase-1
  作者：De-Yun Cui、Yi Yang、Meng-Meng Bai、Jiang-Xue Han、Cong-Cong Wang、Hong-Tao Kong、Bo-Yuan Shen、Da-Chao Yan、Chun-Ling Xiao、Yi-Shuang Liu、En Zhang

  DOI：10.1016/j.bioorg.2020.103965

  日期：2020.8

  New Delhi Metallo-β-lactamase-1 (NDM-1), a Zn (II)-dependent enzyme, can catalyze the hydrolysis of almost all β-lactam antibiotics including carbapenems, resulting in bacterial antibiotic resistance, which threatens public health globally. Based on our finding that H2dedpa is as an efficient NDM-1 inhibitor, a series of H2dedpa derivatives was systematically prepared. These compounds exhibited significant

  新德里Metallo-β-内酰胺酶-1（NDM-1）是一种依赖锌（II）的酶，可以催化几乎所有β-内酰胺抗生素（包括碳青霉烯）的水解，导致细菌对抗生素的耐药性，这在全球范围内威胁着公众健康。基于我们的发现，H 2 dedpa是有效的NDM-1抑制剂，系统地制备了一系列H 2 dedpa衍生物。这些化合物对NDM-1表现出显着的活性，IC 50值为0.06-0.94μM。在体外，化合物6k和6n可以恢复美罗培南对肺炎克雷伯菌，大肠杆菌和变形杆菌的活性。拥有NDM或IMP。特别地，当使用这两种化合物时，美罗培南对产生大肠杆菌的NDM-4的活性可提高至5333倍。基于时间杀伤的细胞分析表明，美罗培南与化合物6k或6n联合使用可杀死99.9％的奇异疟原虫。此外，化合物6k和6n具有非溶血性（HC 50  > 1280μg/ mL），并且对哺乳动物（HeLa）细胞毒性低。机理研究表明，化合物6k和6n通过螯合酶的Zn