(R)-2,3-二氢-1,4-苯并二恶烷-2-甲胺 | 46049-48-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 中文名称: (R)-2,3-二氢-1,4-苯并二恶烷-2-甲胺
• 中文别名: (R)-2,3-二氢-1,4-苯并二噁英-2-甲胺
• 英文名称: (R)-2-((amino)methyl)-1,4-benzodioxane
• 英文别名: (2R)-2(aminomethyl)-1,4-benzodioxane；(2S)-2-aminomethyl-1,4-benzodioxane；(R)-2-aminomethyl-1,4-benzodioxane；(R)-2-(aminomethyl)benzodioxane；2,3-Dihydro-1,4-benzodioxin-2(R)-methanamine；(R)-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanamine；[(3R)-2,3-dihydro-1,4-benzodioxin-3-yl]methanamine
• CAS: 46049-48-3
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: JHNURUNMNRSGRO-SSDOTTSWSA-N

物化性质

• 沸点：
  266.0±19.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P310,P332+P313,P362,P403+P233,P405,P501
• 危险品运输编号：
  2735
• 危险性描述：
  H315,H318,H335

反应信息

• 作为反应物：
  描述：

  (R)-2,3-二氢-1,4-苯并二恶烷-2-甲胺 在 sodium tetrahydroborate 、 sodium meta bi sulfate 、 三氯异氰尿酸 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 5.25h， 生成 (R)-2-(羟基甲基)-1,4-苯并二噁烷
  参考文献：
  名称：

  From 2-Aminomethyl-1,4-benzodioxane Enantiomers to Unichiral 2-Cyano- and 2-Carbonyl-Substituted Benzodioxanes via Dichloroamine

  摘要：

  2-Substituted 1,4-benzodioxanes, such as 2-cyano-, 2-methoxycarbonyl-, 2-aminocarbonyl-, and 2-formyl-1,4-benzodioxane, are key synthons that for the most part are never described as enantiomers or are inadequately characterized for enantiomeric purity. They were prepared by quantitative N,N-dichlorination of (R)- and (S)-2-aminomethyl-1,4-benzodioxane and successive functional group conversions in high yields without any racemization of the stereogenic benzodioxane C(2).

  DOI：

  10.1021/jo500964y
• 作为产物：
  描述：

  (R)-2-(羟基甲基)-1,4-苯并二噁烷 在 吡啶 、 一水合肼 作用下， 以 乙二醇甲醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-2,3-二氢-1,4-苯并二恶烷-2-甲胺
  参考文献：
  名称：

  Ferri; Pallavicini; Piccini, Farmaco, Edizione Scientifica, 1988, vol. 43, # 12 SUPPL., p. 1153 - 1163

  摘要：

  DOI：

文献信息

• Crystallization-based resolution of 1,4-benzodioxane-2-carboxylic acid enantiomers via diastereomeric 1-phenylethylamides
  作者：Laura Fumagalli、Cristiano Bolchi、Francesco Bavo、Marco Pallavicini

  DOI：10.1016/j.tetlet.2016.03.100

  日期：2016.5

  Unlike the diastereomeric 1-phenylethylammonium salts, the diastereomeric N-1-phenylethylamides of (S)- and (R)-1,4-benzodioxane-2-carboxylic acid show significant differences in fusibility and solubility so as to be efficiently resolved by precipitation of the less soluble diastereomer (>98% de), while chromatographic purification of the unprecipitated fraction affords the more soluble one (>99% de)

  与（S）-和（R）-1,4-苯并二恶烷-2-羧酸的非对映异构体N -- 1-苯基乙酰胺不同，在熔解性和溶解度方面存在显着差异，因此可以通过沉淀有效地拆分溶解度较低的非对映异构体（> 98％de），而未沉淀级分的色谱纯化得到溶解度更高的（> 99％de）。总体而言，前者的95％和后者的80％得到了恢复。两种拆分的酰胺的水解以定量收率提供了两种酸对映体和拆分胺，且立体异构体纯度不变。
• Serotonin 5HT1A and 5HT1D antagonists
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0478954A1

  公开（公告）日：1992-04-08

  The present invention is directed to a new class of serotonin 5HT1A agonists and pharmaceutical compositions containing them.

  本发明涉及一类新的血清素 5HT1A 激动剂和含有它们的药物组合物。
• Targeted drugs associated with trimethylamine and/or trimeihylamine-n-oxide
  申请人：Psomagen, Inc.

  公开号：US11424006B2

  公开（公告）日：2022-08-23

  Embodiments of a method and/or system can include administering, to a patient with one or more conditions associated with at least one of TMA, TMAO, and/or derivatives thereof, a therapeutically effective amount of a compound for affecting inhibiting one or more CutC enzymes and/or CntA enzymes associated with microorganisms from at least one taxon from a set of microorganism taxa.

  方法和/或系统的实施方案可包括向患有与 TMA、TMAO 和/或其衍生物中的至少一种相关的一种或多种疾病的患者施用治疗有效量的化合物，以影响抑制与一组微生物类群中至少一个类群的微生物相关的一种或多种 CutC 酶和/或 CntA 酶。
• [EN] COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR DES CYCLOFRUCTANES EN TANT QU'AGENTS DE SÉPARATION
  申请人：UNIV TEXAS

  公开号：WO2010148191A3

  公开（公告）日：2011-05-19
• WB4101-Related Compounds:  New, Subtype-Selective α₁-Adrenoreceptor Antagonists (or Inverse Agonists?)
  作者：Marco Pallavicini、Roberta Budriesi、Laura Fumagalli、Pierfranco Ioan、Alberto Chiarini、Cristiano Bolchi、Maria Paola Ugenti、Simona Colleoni、Marco Gobbi、Ermanno Valoti

  DOI：10.1021/jm060358r

  日期：2006.11.30

  Our previous structure-affinity relationship study had considered the enantiomers of the naphthodioxane, tetrahydronaphthodioxane, and 2-methoxy-1-naphthoxy analogues ( compounds 1, 3, and 2, respectively) of 2-(2,6-dimethoxyphenoxyethylaminomethyl)-1,4-benzodioxane, the well-known alpha(1)-adrenoceptor (alpha(1)-AR) antagonist WB4101, showing that such modifications significantly modulate the affinity and selectivity profile for alpha(1)-AR subtypes and 5-HT1A receptor. Here, we extend investigations to antagonist activity enclosing new enantiomeric pairs, namely those of the methoxytetrahydronaphthoxy and methoxybiphenyloxy WB4101 analogues (4 and 5-7, respectively) and of a double- modified WB4101 derivative ( 8) resulting from hybridization between 2 and 3. We found that (S)-2 is a very potent (pA(2) 10.68) and moderately selective alpha(1D)-AR antagonist and the hybrid (S)-8 is a potent (pA(2) 7.98) and highly selective alpha(1A)-AR antagonist. Both of these compounds and (S)-WB4101 seem to act as inverse agonists in a vascular model. The results, which generally validate the logic we followed in designing these eight compounds, are acceptably rationalized by comparative SAR analysis of binding and functional affinities.