1-(4-chlorophenyl)-N-[2-[(4-chlorophenyl)methylideneamino]ethyl]methanimine | 60434-95-9

• 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-(4-chlorophenyl)-N-[2-[(4-chlorophenyl)methylideneamino]ethyl]methanimine
• 英文别名: (1E,1'E)-N,N'-(ethane-1,2-diyl)bis(1-(4-chlorophenyl)methanimine)；(E,E)-N1,N2-bis(4-chlorobenzylidene)ethane-1,2-diamine；di-(4-chlorobenzal)-ethylenediamine
• CAS: 60434-95-9
• 化学式: C₁₆H₁₄Cl₂N₂
• 分子量: 305.207
• InChiKey: VMWYCJFPSDIEJB-AYKLPDECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  24.72
• 氢给体数：
  0.0
• 氢受体数：
  2.0

安全信息

• 海关编码：
  2921590090

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-N-[2-[(4-chlorophenyl)methylideneamino]ethyl]methanimine 在 锰 、 三氟乙酸 作用下， 以 甲苯 、 乙腈 为溶剂， 以99%的产率得到trans-2,3-bis(4-chlorophenyl)piperazine
  参考文献：
  名称：

  通过锰介导的还原环化的非对映选择性合成哌嗪。

  摘要：

  描述了一种使用布朗斯台德酸和锰（0）的简单有效的合成反式芳基取代的哌嗪的方法。[反应：看文字]

  DOI：

  10.1021/ol034469l
• 作为产物：
  描述：

  4-氯苯甲醛 、 乙二胺 在 polymer supported zinc(II)-salen complex 作用下， 以 水 为溶剂， 反应 2.0h， 以76%的产率得到1-(4-chlorophenyl)-N-[2-[(4-chlorophenyl)methylideneamino]ethyl]methanimine
  参考文献：
  名称：

  容易获得聚合物支撑的锌－salen配合物：高效的非均相催化剂，用于在水性介质中合成乙内酰脲，巯基乙内酰脲和席夫碱

  摘要：

  描述了聚合物负载的锌－salen复合物（PS－Zn－salen）的合成。单核锌（II）–salen配合物的特征在于傅立叶变换NMR光谱，能量色散X射线光谱，傅立叶变换红外光谱（FT-IR），热重分析，扫描电子显微镜，表面积和孔径分布布鲁诺尔-埃米特-特勒。合成的PS-Zn-salen配合物可用作可循环利用的非均相催化剂，用于在水性介质中有效合成乙内酰脲，巯基乙内酰脲和席夫碱。乙内酰脲，巯基乙内酰脲和席夫碱的分离产率分别达到89％，95％和94％。尽管使用了传统的非均相催化剂，目前的PS-Zn-salen配合物仍显示出高达280°C的热稳定性。此外，通过简单的过滤就可以很容易地回收催化剂，并在连续六次运行中活性稍有下降的情况下再用于下一次运行。第6次运行后，循环催化剂的FT-IR光谱证实该催化剂在反应过程中是稳定的。通过AAS和热过滤测试可以确认，从PS-Zn-salen中浸出的金属可以忽略不计。

  DOI：

  10.1007/s11164-017-3215-x

文献信息

• Synthesis and Structural Characterization of (2E,3E)-N1,N2-Bis(4-chlorobenzylidene)ethane-1,2-diamine
  作者：Zu-Pei Liang、Jian Li

  DOI：10.14233/ajchem.2013.12108b

  日期：——

  Present compound (2E,3E)-N1,N2-bis(4-chlorobenzylidene)ethane-1,2-diamine (C16H14Cl4N2, Mr = 305.19) was synthesized and characterized by elemental analysis, FT-IR, 1H NMR and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group Cc, with a = 10.166(2), b = 10.345(2), c = 26.650(5) Å, b = 91.91(3)º, V = 2801.1(10) Å3, Z = 8, Dc = 1.447 g/cm3, l = 0.71073 Å, μ(MoKa) = 0.454 mm-1, F(000) = 1264. The final refinement gave R = 0.0652, wR(F2) = 0.1582 for 4,578 observed reflections with I > 2s(I). X-Ray diffraction analysis reveals that the asymmetric unit of the title compound consists of two independent molecules. Each independent molecule adopts an E configuration about the central C=N functional bond. The dihedral angles between the two benzene rings are 2.3(2) and 0.5(2)º, respectively in two independent molecules. The molecules are linked through C-H···Cl hydrogen bonds interactions.

  合成了化合物(2E,3E)-N1,N2-双(4-氯亚苄基)乙烷-1,2-二胺(C16H14Cl4N2, Mr = 305.19)，并通过元素分析、FT-IR、1H NMR和单晶X进行表征射线衍射。该晶体属于单斜晶系，空间群Cc，a = 10.166(2)，b = 10.345(2)，c = 26.650(5) Å，b = 91.91(3)º，V = 2801.1(10) Å3，Z = 8，Dc = 1.447 g/cm3，l = 0.71073 Å，μ(MoKa) = 0.454 mm-1，F(000) = 1264。对于 4,578 个观察到的反射，最终精修得出 R = 0.0652、wR(F2) = 0.1582 I > 2s(I)。 X射线衍射分析表明标题化合物的不对称单元由两个独立的分子组成。每个独立分子均采用围绕中心 C=N 功能键的 E 构型。两个独立分子中两个苯环之间的二面角分别为 2.3(2) 和 0.5(2)°。分子通过C-H·Cl氢键相互作用连接。
• Electroorganic chemistry. 129. Electroreductive synthesis of chiral piperazines and enantioselective addition of diethylzinc to aldehydes in the presence of the chiral piperazines
  作者：Tatsuya Shono、Naoki Kise、Eiji Shirakawa、Hideshi Matsumoto、Eiichi Okazaki

  DOI：10.1021/jo00009a026

  日期：1991.4

  Electroreduction of diimines, prepared from 1,2-diamines and aromatic aldehydes, in acidic media gave intramolecularly coupled products, 2,3-diarylpiperazines, stereoselectively. Chiral tri- and tetrasubstituted piperazines were synthesized effectively from chiral 1,2-diamines by the same electroreductive method. Chiral piperazines, prepared from 1(R),2(R)-diaminocyclohexane were effective chiral ligands of catalysts for the enantioselective addition of diethylzinc to aldehydes.
• 3,3′-Di [1,3-thiazolidine-4-one] system. II. Anti-inflammatory and anti-histaminic properties in new substituted derivatives
  作者：Tindara Previtera、Maria Basile、Maria Gabriella Vigorita、Giovanna Fenech、Francesco Occhiuto、Clara Circosta、Rita Costa de Pasquale

  DOI：10.1016/0223-5234(87)90175-9

  日期：1987.1
• A New Family of Doubly Cyclopalladated Diimines. A Remarkable Effect of the Linker between the Metalated Units on Their Cytotoxicity
  作者：Joan Albert、Ramon Bosque、Magali Cadena、Lucía D’Andrea、Jaume Granell、Asensio González、Josefina Quirante、Carmen Calvis、Ramon Messeguer、Josefa Badía、Laura Baldomà、Teresa Calvet、Mercè Font-Bardia

  DOI：10.1021/om500382f

  日期：2014.6.9

  The cyclopalladation of a series of symmetric diimines with the formula (RC6H4CH=NZ)(2), where Z = CH2 or (CH2)(2)OCH2 and R = p-Cl, p-OMe, p-NO2, and o-Cl, is described. Optimal conditions to obtain the dimetalated compounds were found to be palladium(II) acetate, in toluene, at 60 degrees C and with a reaction time of 2-4 h. The reactivity of the dimetalated compounds with monodentate, bidentate, and bis(monodentate) Lewis bases was also studied. The cytotoxic activity of some selected compounds was evaluated against a panel of adenocarcinoma cell lines (colon HCT116 and breast MCF7 and MDA-MB231). Compounds containing the fragment NCH2CH2OCH2CH2OCH2CH2N exhibited a remarkable cytotoxic activity in the three cancer cells assayed, but complexes containing the NCH2CH2N fragment showed no activity. It seems that the length and flexibility of the central saturated chain in the imine molecule, as well as its lipophilicity and hydrophilicity, explain the different cytotoxicity of the two series of coordination compounds here reported.
• A Simple Method of Synthesis of (±)-2,3-Diarylpiperazines and a Novel Method of Resolution of (±)-2,3-Diphenylpiperazine
  作者：Pothiappan Vairaprakash、Mariappan Periasamy

  DOI：10.1021/jo060083n

  日期：2006.4.1

  Intramolecular reductive coupling of diimines in the presence of Zn/Ti((OPr)-Pr-i)(2)Cl-2 gives the corresponding (+/-)-2,3-diarylpiperazines in 73-83% yields with dl/meso ratio > 99%: < 1%. The (+/-)-2,3-diphenylpiperazine obtained in this way was readily resolved partially using L-(+)-tartaric acid, and the enantiomeric purity was enhanced to > 99% ee via preparation of hydrogen-bonded salt aggregates using oxalic acid.