4t,4't-methanediyl-bis-cyclohex-r-ylamine | 6693-29-4

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4t,4't-methanediyl-bis-cyclohex-r-ylamine
• 英文别名: trans,trans-4,4′-diaminocyclohexylmethane；(trans,trans)-4,4'-diamino(dicyclohexylmethane)；trans,trans-4,4'-methylenebis(cyclohexylamine)；trans,trans-4,4'-diaminodicyclohexylmethane；4,4'-diaminodicyclohexylmethane；4t,4't-methanediyl-bis-cyclohex-r-ylamine；4t,4't-Methandiyl-bis-cyclohex-r-ylamin
• CAS: 6693-29-4
• 化学式: C₁₃H₂₆N₂
• 分子量: 210.363
• InChiKey: DZIHTWJGPDVSGE-NGBBIHDVSA-N

物化性质

• 熔点：
  64.7°C
• 沸点：
  339.9°C (rough estimate)
• 密度：
  0.9578 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.04
• 氢给体数：
  2.0
• 氢受体数：
  2.0

安全信息

• 海关编码：
  2921300090

反应信息

• 作为反应物：
  描述：

  4t,4't-methanediyl-bis-cyclohex-r-ylamine 在 甲酸 、 sodium nitrite 作用下， 反应 2.0h， 生成 3,3'-(methanediyldicyclohexane-4,1-diyl)bis[1-(2-chloroethyl)-1-nitrosourea]
  参考文献：
  名称：

  Synthesis of analogs of N-(2-chloroethyl)-N'-(trans-4-methylcyclohexyl)-N-nitrosourea for evaluation as anticancer agents

  摘要：

  The superior activity of N-(2-chloroethyl)-N'-(trans-4-methylcyclohexyl)-N-nitrosourea (MeCCNU) against advanced murine Lewis lung carcinoma in comparisons with the cis form and other nitrosoureas prompted the synthesis of a number of MeCCNU analogues, including several cis-trans pairs. The methyl group was replaced by a variety of substituents (CO2H, CH2CO2H, CO2Me, CH2OAc, CH2Cl, OMe); the trans-3-methylcyclohexyl, cis-2-methyl-1,3-dithian-5-yl, cis- and trans-2-methyl-1,3-dithian-5-yl-tetraoxide, and 1-methylhexyl (open-chain) analogues were also prepared. Preliminary tests against murine leukemia L1210 revealed therapeutic indices (ED50/LD10) ranging from 0.26 to 0.79; all but three analogues effected 50% cure rates at nontoxic doses, the open-chain analogue being one of the least active. In terms of therapeutic index, diequatorial (trans-4) isomers were, with one exception, as active as or, in four of the eight examples, somewhat more active than the corresponding axial-equatorial (cis-4) isomers. In this series, four of the five 2-fluoroethyl analogues prepared were clearly inferior to the corresponding 2-chloroethyl analogues.

  DOI：

  10.1021/jm00212a019
• 作为产物：
  描述：

  4,4'-二氨基二环己基甲烷 生成 4t,4't-methanediyl-bis-cyclohex-r-ylamine
  参考文献：
  名称：

  Mesch, Chemiker-Zeitung, Chemische Apparatur, 1971, p. 554

  摘要：

  DOI：

文献信息

• Ceria supported Ru0-Ru+ clusters as efficient catalyst for arenes hydrogenation
  作者：Yanwei Cao、Huan Zheng、Gangli Zhu、Haihong Wu、Lin He

  DOI：10.1016/j.cclet.2020.05.045

  日期：2021.2

  was developed for aromatic amines hydrogenation with excellent activity and selectivity under relative milder conditions. The morphology, electronic and chemical properties, especially the Ru0-Ruδ+ clusters and reducible ceria were characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electronic microscopy (SEM), X-ray photoelectron spectroscopy (XPS), CO2 temperature

  由于广泛的应用，芳香胺的选择性加氢特别是非黄变聚氨酯的化学加成尤其受到关注，例如苯胺和双（4-氨基环己基）甲烷等化学物质。征服在选择性氢化存在的困难，在Ru 0 -Ru δ + /的CeO 2催化剂用固体沮丧路易斯对是为芳香胺氢化相对较温和的条件下具有优异的活性和选择性显影。形态，电子和化学性能，尤其是在Ru 0 -Ru δ +通过X射线衍射（XRD），透射电子显微镜（TEM），扫描电子显微镜（SEM），X射线光电子能谱（XPS），CO 2程序升温脱附（CO 2 -TPD）对簇和可还原二氧化铈进行了表征H 2程序升温还原（H 2 -TPR），H 2漫反射傅里叶变换红外光谱（H 2 -DRIFT），拉曼等。2％Ru / CeO 2催化剂显示出对环己胺的95％的良好转化率和大于99％的选择性。发现描述活动和Ru状态的火山曲线。由于周围碱性位点的“酸性位点隔离”，可以有效地抑制相邻胺分子之间的缩
• Novel bisnaphthalimidopropyl (BNIPs) derivatives as anticancer compounds targeting DNA in human breast cancer cells
  作者：Maria Kopsida、Gemma A. Barron、Giovanna Bermano、Paul Kong Thoo Lin、Marie Goua

  DOI：10.1039/c6ob01850e

  日期：——

  (72.3–29.5% yield) and characterised by nuclear magnetic resonance spectroscopy (NMR) and mass spectrometry (MS). Competitive displacement of ethidium bromide (EtBr) and UV binding studies were used to study the interactions of BNIP derivatives with Calf Thymus DNA. The cytotoxicity of these derivatives was assessed against human breast cancer MDA-MB-231 and SKBR-3 cells by MTT assay. Propidium iodide

  双萘二甲酰亚胺丙基（BNIP）衍生物是一类在体外发挥抗癌活性的化合物，根据以前的研究，接头序列的变化增加了其DNA结合和细胞毒性活性。通过修改双萘二甲酰亚胺丙基二氨基二环己基甲烷（BNIPDaCHM），一种先前合成的具有抗癌特性的BNIP衍生物的接头序列，设计了三种新型的BNIP衍生物。Bisnaphthalimidopropyl-piperidylpropane（BNIPPiProp），BNIPDaCHM的结构异构体，bisnaphthalimidopropyl ethylenedipiperidine二氢溴酸盐（BNIPPiEth），BNIPDaCHM的用较短的连接基团链，和（同种型反式（反式）） -二氨基bisnaphthalimidopropyl（反式，反式-BNIPDaCHM）是BNIPDaCHM的立体异构体，已成功合成（收率72.3–29.5％），并通过核磁共振波谱（NMR）和
• Ni-Catalyzed reductive amination of phenols with ammonia or amines into cyclohexylamines
  作者：Thomas Cuypers、Thomas Morias、Simon Windels、Carlos Marquez、Cédric Van Goethem、Ivo Vankelecom、Dirk E. De Vos

  DOI：10.1039/c9gc02625h

  日期：——

  for alicyclic compounds, such as primary and N-substituted cyclohexylamines. So far, the latter are mostly produced from non-renewable starting materials like benzene via problematic nitration/reduction or cross-coupling routes. Herein, an efficient reductive amination of phenol with ammonia or amines is demonstrated, for the first time without the need for rare and expensive noble metals and without

  天然存在于木质纤维素中的苯酚及其衍生物不仅可以用于芳族化合物，还可以用于脂环族化合物（例如伯和N-取代的环己胺）作为可再生原料。到目前为止，后者主要由不可再生的原材料（例如苯）经硝化/还原或交叉偶联途径有问题。在本文中，首次证明了苯酚与氨或胺的有效还原胺化，而无需稀有和昂贵的贵金属且无需使用任何添加剂。筛选了各种负载型Ni催化剂，我们阐明了关键参数的影响，包括载体材料的酸碱性质。然后将获得的知识应用于不同的苯酚-氨/胺组合，从而以相当高的收率合成了各种伯，仲和叔环己胺。
• METHOD FOR PREPARING DIAMINO-DICYCLOHEXYL METHANE
  申请人：WANHUA CHEMICAL GROUP CO., LTD.

  公开号：US20160068472A1

  公开（公告）日：2016-03-10

  Disclosed is a method for preparing diamino-dicyclohexyl methane (H 12 MDA) by hydrogenation of diamino-diphenyl methane (MDA). In the process, 4,4′-MDA used as the starting material is firstly hydrogenated to prepare 4,4′-H 12 MDA. When the activity of the catalyst is reduced, the feed is switched from 4,4′-MDA to the mixture of 2,4′-MDA and 4,4′-MDA, and then when the conversion is stabilized, the feed is switched to 4,4′-MDA again. The deactivated catalyst is activated on line by switching the feed to the mixture of 2,4′-MDA and 4,4′-MDA. 4,4′-H 12 MDA having the trans-trans isomer content of 16˜24 wt % is produced, and the mixture of 2,4′-H 12 MDA and 4,4′-H 12 MDA is also produced, wherein the content of 2,4′-H 12 MDA in the mixture is 4˜15 wt %.

  本发明公开了一种通过氢化二氨基二苯甲烷（MDA）制备二氨基二环己基甲烷（H12MDA）的方法。在该过程中，首先将起始材料4,4'-MDA氢化制备4,4'-H12MDA。当催化剂活性降低时，将进料从4,4'-MDA切换到2,4'-MDA和4,4'-MDA的混合物，当转化稳定后，再将进料切换回4,4'-MDA。失活的催化剂通过将进料切换到2,4'-MDA和4,4'-MDA的混合物上线活化。制备出具有16~24重量％的顺式-顺式异构体含量的4,4'-H12MDA，以及2,4'-H12MDA和4,4'-H12MDA的混合物，其中混合物中2,4'-H12MDA的含量为4~15重量％。
• PROCESS FOR HYDROGENATING 4,4'-METHYLENEDIANILINE
  申请人：BASF SE

  公开号：US20160326094A1

  公开（公告）日：2016-11-10

  The present invention relates to a process for hydrogenating 4,4′-methylenedianiline and/or polymeric MDA with hydrogen in the presence of a catalyst comprising ruthenium on a zirconium oxide support material, and also to the use of a catalyst comprising ruthenium on a zirconium oxide support material for hydrogenating 4,4′-methylenedianiline and/or polymeric MDA.

  本发明涉及一种在氢气存在下使用以锆氧化物支撑材料上的钌为催化剂对4,4'-亚甲基二苯胺和/或聚合物MDA进行氢化的过程，以及使用含有锆氧化物支撑材料上的钌作为催化剂对4,4'-亚甲基二苯胺和/或聚合物MDA进行氢化的方法。