1,3,5-tris(2'-fluorophenyl)-hexahydro-1,3,5-triazine | 83734-38-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,3,5-tris(2'-fluorophenyl)-hexahydro-1,3,5-triazine
• 英文别名: 1,3,5-tris-(o-fluorophenyl)-1,3,5-triazacyclohexane；1,3,5-tris(2-fluorophenyl)-1,3,5-triazinane；1,3,5-tris(2-fluorophenyl)-hexahydro-s-triazine
• CAS: 83734-38-7
• 化学式: C₂₁H₁₈F₃N₃
• 分子量: 369.389
• InChiKey: ODIAJWCYDCCBMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3,5-tris(2'-fluorophenyl)-hexahydro-1,3,5-triazine 生成 N-(2-fluorophenyl)methanimine
  参考文献：
  名称：

  Giumanini, Angelo G.; Verardo, Giancarlo; Zangrando, Ennio, Journal fur praktische Chemie (Leipzig 1954), 1987, vol. 329, # 6, p. 1087 - 1103

  摘要：

  DOI：
• 作为产物：
  描述：

  聚合甲醛 、 2-氟苯胺 以 水 为溶剂， 反应 0.42h， 以93%的产率得到1,3,5-tris(2'-fluorophenyl)-hexahydro-1,3,5-triazine
  参考文献：
  名称：

  Task-specific Ionic Liquid-mediated Facile Synthesis of 1,3,5-Triaryltriazines by Cyclotrimerization of Imines and Their Biological Evaluation

  摘要：

  高效合成氟化1,3,5-三芳基三嗪衍生物的方法是通过芳香胺与甲醛的缩合反应，随后在室温下使用特定任务的1,1,3,3-四甲基胍三氟乙酸盐[TMG][Tfa]离子液体作为环境友好型溶剂进行自发环三聚化，产率优异。所合成的化合物在Löwenstein-Jensen培养基中针对结核分枝杆菌H37Rv株进行了体外抗结核活性测试。

  DOI：

  10.1246/cl.130839

文献信息

• 一种手性α-季碳-α-羟基-β-氨基酮衍生物及 其合成方法
  申请人：华东师范大学

  公开号：CN109896969B

  公开（公告）日：2021-12-07

  本发明公开了一种手性α‑季碳‑α‑羟基‑β‑氨基酮的合成方法，以醇、重氮化合物及1,3,5‑三芳基‑1,3,5‑三嗪为原料，Rh2(esp)2为催化剂，手性磷酸(CPA)作为共催化剂，在有机溶剂中，分子筛为添加剂，经过一步三组分反应高立体选择性、高收率的得到产物。本发明的方法具有原子经济性高、立体选择性好、反应条件温和、收率高、操作简单安全等优点。实现了羟基叶立德的不对称胺甲基化反应，合成了一系列光学纯的α‑季碳‑α‑羟基‑β‑氨基酮衍生物。
• Task-specific Ionic Liquid-mediated Facile Synthesis of 1,3,5-Triaryltriazines by Cyclotrimerization of Imines and Their Biological Evaluation
  作者：Anshu Dandia、Anuj K. Jain、Sonam Sharma

  DOI：10.1246/cl.130839

  日期：2014.4.5

  A highly efficient method for the synthesis of fluorinated 1,3,5-triaryltriazine derivatives is developed by the condensation reaction of aromatic amines and formaldehyde followed by spontaneous cyclotrimerization using task-specific 1,1,3,3-tetramethylguanidine trifluoroacetate [TMG][Tfa] ionic liquid as a environmentally benign solvent in excellent yields at room temperature. The synthesized compounds were subjected for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv strain using the Löwenstein–Jensen medium.

  高效合成氟化1,3,5-三芳基三嗪衍生物的方法是通过芳香胺与甲醛的缩合反应，随后在室温下使用特定任务的1,1,3,3-四甲基胍三氟乙酸盐[TMG][Tfa]离子液体作为环境友好型溶剂进行自发环三聚化，产率优异。所合成的化合物在Löwenstein-Jensen培养基中针对结核分枝杆菌H37Rv株进行了体外抗结核活性测试。
• Synthesis, molecular structure, conformation and biological activity of Ad-substituted N-aryl-tetraoxaspiroalkanes
  作者：Tatyana V. Tyumkina、Nataliya N. Makhmudiyarova、Guzeliya M. Kiyamutdinova、Ekaterina S. Meshcheryakova、Kamil Sh. Bikmukhametov、Marat F. Abdullin、Leonard M. Khalilov、Askhat G. Ibragimov、Usein M. Dzhemilev

  DOI：10.1016/j.tet.2018.01.045

  日期：2018.4

  An efficient method has been developed for the synthesis of 7′-arylspiroadamantane-[2,3′]-(1′,2′,4′,5′,7′-tetraoxazocanes)} by the ring transformation reaction of spiroadamantane-[2,3’]-(1′,2′,4′,5′,7′-pentaoxacane)} with arylamines in the presence of Sm(NO3)3·6H2O as the catalyst. NMR signals of the synthesized compounds were assigned considering the conformation dynamics of the tetraoxazocane ring

  通过螺环的环转化反应，已开发出一种有效的方法来合成7'-芳基螺adamantane- [2,3']-（1'，2'，4'，5'，7'-四恶唑烷）}在Sm（NO 3）3 ·6H 2存在下，用芳基胺adamantane- [2,3']-（1'，2'，4'，5'，7'-五氧六环）}}以O为催化剂。考虑到具有两个刚性过氧化物键的四恶唑烷环的构象动力学，对合成化合物的NMR信号进行了分配。通过X射线衍射研究了某些化合物的结构。用DSC法测定单晶的热稳定性。化合物7'-（2-甲基苯基）螺金刚烷-[2,3']-（1'，2'，4'，5'，7'-四恶唑烷）}和7'-（4-氟苯基）螺金刚烷-[2,3']-（1'，2'，4'，5'，7'-四恶唑烷）}对癌细胞具有细胞毒性。
• Thiadiazines, and insecticidal and acaricidal preparations
  申请人：Mitsui Toatsu Chemicals, Inc.

  公开号：US05021412A1

  公开（公告）日：1991-06-04

  Novel tetrahydro-1,3,5-thiadiazin-4-ones of the following general formula (I) or their salts which are useful as an insecticidal and acaricidal agent. ##STR1## In the formula, each of R.sup.1 and R.sup.2 represents a halogen atom or a C.sub.1 -C.sub.4 alkyl group; R.sup.3 represents a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.1 -C.sub.4 alkoxy group, an acetyl group, a phenoxy group, a halo-substituted phenoxy group, a benzyl group, a benzyloxy group, a phenylcarbonyl group, a C.sub.1 -C.sub.4 haloalkyloxy group, a C.sub.1 -C.sub.4 haloalkyloxymethyl group, a C.sub.2 -C.sub.4 haloalkenyloxy group, a C.sub.1 -C.sub.4 haloalkylthio group, a C.sub.1 -C.sub.4 haloalkylthiomethyl group, a C.sub.2 -C.sub.4 haloalkenylthio group, a C.sub.1 -C.sub.8 haloalkyl group, a C.sub.2 -C.sub.8 haloalkenyl group, a C.sub.1 -C.sub.8 alkyloxycarbonyl group, a substituted phenoxycarbonyl group, or a substituted pyridyloxy group; m represents 0, 1, 2 or 3; and n represents 0, 1, 2 or 3. These novel thiadiazines are produced by reacting a compound of general formula (II) ##STR2## wherein R.sup.1 and m are as defined above, with a compound of general formula (III) ##STR3## wherein R.sup.2, R.sup.3 and n are as defined above.

  以下是通用公式（I）的新型四氢-1,3,5-噻二唑-4-酮或其盐，可用作杀虫剂和杀螨剂。在该公式中，R.sup.1和R.sup.2中的每一个代表卤素原子或C.sub.1-C.sub.4烷基；R.sup.3代表卤素原子，C.sub.1-C.sub.4烷基，C.sub.3-C.sub.6环烷基，C.sub.1-C.sub.4烷氧基，乙酰基，苯氧基，卤素取代的苯氧基，苄基，苄氧基，苯甲酰基，C.sub.1-C.sub.4卤代烷氧基，C.sub.1-C.sub.4卤代烷氧甲基，C.sub.2-C.sub.4卤代烯基氧基，C.sub.1-C.sub.4卤代烷硫基，C.sub.1-C.sub.4卤代烷硫甲基，C.sub.2-C.sub.4卤代烯基硫基，C.sub.1-C.sub.8卤代烷基，C.sub.2-C.sub.8卤代烯基，C.sub.1-C.sub.8烷氧羰基，取代的苯氧羰基，或取代的吡啶氧基；m代表0, 1, 2或3；n代表0, 1, 2或3。这些新型噻二唑通过将通用公式（II）的化合物与通用公式（III）的化合物反应而制备而成。
• <i>N</i>-Nitroso-<i>N</i>-(<i>n</i>-butoxymethyl)arylamines
  作者：Giancarlo Verardo、Angelo G. Giumanini、Fausto Gorassini、Paolo Strazzolini

  DOI：10.1246/bcsj.68.1361

  日期：1995.5

  The title compounds were promptly obtained in fair to good yields as distillable liquids by admixing 1,3,5-triarylhexahydro-1,3,5-triazines (1) with n-butyl nitrite (2) in anhydrous CH2Cl2 and were fully characterized by 1H and 13C NMR, IR, and MS. The pure products were invariably made up of geometric isomers which did not interconvert rapidly at room temperature. o-Substituents could cause difficulties in the free rotations of the aryl substituent about the C–N bond as well of the α-butoxymethyl group. The reaction is believed to occur on the monomeric imines derived from the thermal equilibration of their trimeric and dimeric precursors. Aliphatic hexahydrotriazines were found to be unreactive under the present conditions.

  标题化合物以适中的至良好的产率迅速获得，作为可蒸馏液体，通过在无水CH2Cl2中将1,3,5-三芳基六氢-1,3,5-三嗪（1）与正丁基亚硝酸酯（2）混合，并通过1H和13C NMR、IR和质谱进行了全面表征。纯产品始终由几何异构体组成，这些异构体在室温下不会快速相互转化。邻位取代基可能会导致芳基取代基绕C–N键的自由旋转和α-丁氧基甲基团的自由旋转出现困难。反应被认为发生在从其三聚体和二聚体前体的热平衡中衍生的单体亚胺上。在现有条件下，脂肪族六氢三嗪被发现不活泼。