trans-(2-phenyl-[1,3]dioxan-5-yl)-amine | 13042-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: trans-(2-phenyl-[1,3]dioxan-5-yl)-amine
• 英文别名: trans-(2-phenyl-1,3-dioxan-5-yl)amine
• CAS: 13042-45-0
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: XXLVLPPHZWTLGD-MGCOHNPYSA-N

物化性质

• 熔点：
  58-60 °C
• 沸点：
  296.6±40.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trans-(2-phenyl-[1,3]dioxan-5-yl)-amine 、 苯甲酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 N-(trans-2-phenyl-1,3-dioxan-5-yl)benzamide
  参考文献：
  名称：

  Toward the development of chemoprevention agents. Part II: Chemo-enzymatic synthesis and anti-inflammatory activities of a new class of 5-amino-2-substitutedphenyl-1,3-dioxacycloalkanes

  摘要：

  A new series of optically pure 5-amino-2-substitutedphenyl-1,3-dioxacyclozilkanes were designed and synthesized via a chemo-enzymatic combined method to develop new chemoprevention agents. Twenty-four of newly synthesized compounds significantly inhibited xylene-induced rat ear edema and exhibited comparable or better anti-inflammatory activities than the reference drug aspirin. Treatment of these anti-inflammatory agents did not prolong the tail bleeding time in rat. In addition, 5-amino-2-substitutedphenyl- I 3-dioxacycloalkanes exhibited good membrane permeability based on in vitro Caco-2 cell monolayer permeability assay. Furthermore, some preliminary structure-activity relationships were further analyzed among these compounds. Taken together, 5-amino-2-substitutedphenyl-1,3-dioxacycloalkanes may represent a new class of anti-inflammatory drugs with safer pharmacological profile. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.018
• 作为产物：
  描述：

  N-(trans-2-phenyl-1,3-dioxan-5-yl)phenylacetamide 在 盐酸 、 penicillin acylase 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 trans-(2-phenyl-[1,3]dioxan-5-yl)-amine
  参考文献：
  名称：

  Toward the development of chemoprevention agents. Part II: Chemo-enzymatic synthesis and anti-inflammatory activities of a new class of 5-amino-2-substitutedphenyl-1,3-dioxacycloalkanes

  摘要：

  A new series of optically pure 5-amino-2-substitutedphenyl-1,3-dioxacyclozilkanes were designed and synthesized via a chemo-enzymatic combined method to develop new chemoprevention agents. Twenty-four of newly synthesized compounds significantly inhibited xylene-induced rat ear edema and exhibited comparable or better anti-inflammatory activities than the reference drug aspirin. Treatment of these anti-inflammatory agents did not prolong the tail bleeding time in rat. In addition, 5-amino-2-substitutedphenyl- I 3-dioxacycloalkanes exhibited good membrane permeability based on in vitro Caco-2 cell monolayer permeability assay. Furthermore, some preliminary structure-activity relationships were further analyzed among these compounds. Taken together, 5-amino-2-substitutedphenyl-1,3-dioxacycloalkanes may represent a new class of anti-inflammatory drugs with safer pharmacological profile. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.018

文献信息

• Ammonium Chloride‐Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation
  作者：Chunling Blue Lan、Karine Auclair

  DOI：10.1002/ejoc.202101059

  日期：2021.10.7

  Ammonium chloride promotes the selective formation of monosubstituted ureas under microwave irradiation. Most nucleophiles, acid-labile functionalities, and protecting groups are well tolerated in this reaction. By avoiding transition metals and mineral acids, this methodology offers a more sustainable alternative for the synthesis of monosubstituted ureas and their analogs.

  氯化铵在微波辐射下促进单取代脲的选择性形成。大多数亲核试剂、酸不稳定官能团和保护基团在该反应中具有良好的耐受性。通过避免过渡金属和无机酸，该方法为合成单取代脲及其类似物提供了一种更可持续的替代方案。
• Conformational Analysis of 5-Substituted 1,3-Dioxanes. 7. Effect of Lithium Bromide Addition^,¹
  作者：Eusebio Juaristi、Francisco Díaz、Geiser Cuéllar、Hugo A. Jiménez-Vázquez

  DOI：10.1021/jo9610117

  日期：1997.6.13

  The position of equilibria, established by means of BF3, between diastereomeric cis- and trans-5-substituted-2-phenyl-1,3-dioxanes, in solvents THF and CHCl3, and in the presence of 0, 1, and 10 equiv of LiBr has been determined. The observed Delta G degrees values show that the addition of salt to the reaction medium influences the position of equilibrium. Lithium bromide effects on the conformational behavior are discussed in terms of lithium ion complexation events that lead to increased stability of the axial isomers when the substituent at C(5) is CO2H, CO2CH3, CONHCH3, and CH2OH. By contrast, disruption of the intramolecular hydrogen bond present in the axial 5-acetamido derivative (cis-9 substituent equal to NHCOCH3) modifies the preference for the axial conformation in salt-free 9 to a net dominance of the equatorial isomer in the presence of LiBr. Interpretation of the experimental observations was based on models that are apparently supported by semiempirical AM1 calculations. The results derived from the present study contribute to our understanding of the processes involved in molecular recognition and may model salt effects in physiological events.
• Synthesis and CB1 receptor activities of dimethylheptyl derivatives of 2-arachidonoyl glycerol (2-AG) and 2-arachidonyl glyceryl ether (2-AGE)
  作者：Teija Parkkari、Outi M.H. Salo、Kristiina M. Huttunen、Juha R. Savinainen、Jarmo T. Laitinen、Antti Poso、Tapio Nevalainen、Tomi Järvinen

  DOI：10.1016/j.bmc.2005.12.007

  日期：2006.4

  Results from a factor analysis and activity studies of commercially available endocannabinoid-type compounds set the starting point for the current study where dimethylheptyl (DMH) analogues of two endocannabinoids, 2-arachidonoyl glycerol (2-AG) and 2-arachidonyl glyceryl ether (2-AGE), were synthesized and their ability to activate the CB1 receptors was determined by the [S-35]GTP gamma S binding assay using rat cerebellar membranes. The main goal of the study was to examine how the DMH end tail affects the activity properties of 2-AG (1) and its stable ether (2) and Urea analogues (5). The importance of the chain length was also explored by synthesizing 2-AG and 2-AGE derivatives (3 and 4) possessing the chain length C-21 instead of C-22. Replacement of the pentyl end chain with the DMH resulted in distinct potency decrease as compared to the reference compounds. The modification did not have Such a strong impact on the efficacy values. In fact, the efficacy of the derivatives of 2-AGE (2 and 4) was comparable or even improved. Introducing a more stable and hydrophilic urea bond led to a dramatic decrease in biological activity. (c) 2005 Elsevier Ltd. All rights reserved.
• Toward the development of chemoprevention agents. Part II: Chemo-enzymatic synthesis and anti-inflammatory activities of a new class of 5-amino-2-substitutedphenyl-1,3-dioxacycloalkanes
  作者：Keli Gu、Lanrong Bi、Ming Zhao、Chao Wang、Jingfang Ju、Shiqi Peng

  DOI：10.1016/j.bmc.2007.06.018

  日期：2007.9

  A new series of optically pure 5-amino-2-substitutedphenyl-1,3-dioxacyclozilkanes were designed and synthesized via a chemo-enzymatic combined method to develop new chemoprevention agents. Twenty-four of newly synthesized compounds significantly inhibited xylene-induced rat ear edema and exhibited comparable or better anti-inflammatory activities than the reference drug aspirin. Treatment of these anti-inflammatory agents did not prolong the tail bleeding time in rat. In addition, 5-amino-2-substitutedphenyl- I 3-dioxacycloalkanes exhibited good membrane permeability based on in vitro Caco-2 cell monolayer permeability assay. Furthermore, some preliminary structure-activity relationships were further analyzed among these compounds. Taken together, 5-amino-2-substitutedphenyl-1,3-dioxacycloalkanes may represent a new class of anti-inflammatory drugs with safer pharmacological profile. (c) 2007 Elsevier Ltd. All rights reserved.