(R)-(-)-1-(8-bromobenzo[1,2-b;4,5-b']difuran-4-yl)-2-aminopropane | 502759-67-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (R)-(-)-1-(8-bromobenzo[1,2-b;4,5-b']difuran-4-yl)-2-aminopropane
• 英文别名: 2-amino-1-(8-bromobenzo[1,2-b:4,5-b']difuran-4-yl)propane；bromodragonfly；BDF；Bromo-DragonFLY；(2R)-1-(4-bromofuro[2,3-f][1]benzofuran-8-yl)propan-2-amine
• CAS: 502759-67-3
• 化学式: C₁₃H₁₂BrNO₂
• 分子量: 294.148
• InChiKey: GIKPTWKWYXCBEC-SSDOTTSWSA-N

物化性质

• 沸点：
  390.2±37.0 °C(Predicted)
• 密度：
  1.525±0.06 g/cm3(Predicted)
• 碰撞截面：
  158.1 Ų [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-二硝基水杨酸 、 (R)-(-)-1-(8-bromobenzo[1,2-b;4,5-b']difuran-4-yl)-2-aminopropane 以 乙醇 、 水 为溶剂， 反应 0.17h， 生成 1-(8-bromobenzo[1,2-b:5,4-b']difuran-4-yl)propan-2-aminium 2-carboxy-4,6-dinitrophenolate
  参考文献：
  名称：

  Crystallographic characterization of the first reported crystalline form of the potent hallucinogen (R)-2-amino-1-(8-bromobenzo[1,2-b;5,4-b′]difuran-4-yl)propane or `bromodragonfly': the 1:1 anhydrous proton-transfer compound with 3,5-dinitrosalicylic acid

  摘要：

  The 1: 1 proton-transfer compound of the potent substituted amphetamine hallucinogen (R)-2-amino-1-(8-bromobenzo[1,2-b;5,4-b']difuran-4-yl)propane (common trivial name 'bromodragonfly') with 3,5-dinitrosalicylic acid, namely 1-(8-bromobenzo[1,2-b;5,4-b']difuran-4-yl)propan-2-aminium 2-carboxy-4,6-dinitrophenolate, C13H13BrNO2+center dot C7H3N2O7-, forms hydrogen-bonded cation-anion chain substructures comprising undulating head-to-tail anion chains formed through C(8) carboxyl-nitro O-H center dot center dot center dot O associations and incorporating the aminium groups of the cations. The intrachain cation-anion hydrogen-bonding associations feature proximal cyclic R-3(3)(8) interactions involving both an N+-H center dot center dot center dot O-phenolate and the carboxyl-nitro O-H center dot center dot center dot O associations and aromatic pi-pi ring interactions [minimum ring centroid separation = 3.566 (2) angstrom]. A lateral hydrogen-bonding interaction between the third aminium H atom and a carboxyl O-atom acceptor links the chain substructures, giving a two-dimensional sheet structure. This determination represents the first of any form of this compound and is in the (R) absolute configuration. The atypical crystal stability is attributed both to the hydrogen-bonded chain substructures provided by the anions, which accommodate the aminium proton-donor groups of the cations and give crosslinking, and to the presence of the cation-anion aromatic ring pi-pi interactions.

  DOI：

  10.1107/s0108270110012850
• 作为产物：
  描述：

  2,3,6,7-四氢呋喃并[2,3-f][1]苯并呋喃 在 三乙基硅烷 、 sodium hydroxide 、 三氯化铝 、 溴 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 50.5h， 生成 (R)-(-)-1-(8-bromobenzo[1,2-b;4,5-b']difuran-4-yl)-2-aminopropane
  参考文献：
  名称：

  对映体的合成和一系列超强，构象受限的5-HT（2A / 2C）受体激动剂的药理学评价。

  摘要：

  配体对5-HT（2A）或5-HT（2C）激动剂结合位点的亲和力通过修饰典型的致幻性苯丙胺（如4b（DOB））中的2,5-氧取代基来增强。相对于母体2，5-二甲氧基化合物，构象柔性的2，5-二甲氧基取代基限制为稠合的二氢呋喃环通常导致效力增加。这些芳基烷基胺的纯对映体是通过对映体特异性合成得到的，该合成涉及用N-三氟乙酰基保护的D-或L-丙氨酰氯对杂环核7进行酰化，然后进行酮还原和N-脱保护。对映异构体在两个受体上显示适度的立体选择性。在它们的药理研究过程中，观察到了这些新化合物类别中的一些一般趋势。对于大多数测试的光学异构体对，在5-HT（2A）和5-HT（2C）受体上，含杂环7的化合物的R-对映体仅比其S-对映体具有更高的亲和力。同样，功能研究表明，与S-对映体相比，R-对映体通常显示出更高的效价。这些芳基烷基胺的二氢呋喃环的芳香化进一步增加了亲和力和效力。仅有少数化合物是完全激动剂，其

  DOI：

  10.1021/jm000491y

文献信息

• Enantiospecific Synthesis and Pharmacological Evaluation of a Series of Super-Potent, Conformationally Restricted 5-HT_2A/2C Receptor Agonists
  作者：James J. Chambers、Deborah M. Kurrasch-Orbaugh、Matthew A. Parker、David E. Nichols

  DOI：10.1021/jm000491y

  日期：2001.3.1

  D- or L-alanyl chloride, followed by ketone reduction and N-deprotection. The enantiomers demonstrated modest stereoselectivity at the two receptors. Several general trends within these classes of new compounds were observed during their pharmacological investigation. For most pairs of optical isomers tested, the R-enantiomers of the compounds containing heterocycle 7 bound with only slightly higher

  配体对5-HT（2A）或5-HT（2C）激动剂结合位点的亲和力通过修饰典型的致幻性苯丙胺（如4b（DOB））中的2,5-氧取代基来增强。相对于母体2，5-二甲氧基化合物，构象柔性的2，5-二甲氧基取代基限制为稠合的二氢呋喃环通常导致效力增加。这些芳基烷基胺的纯对映体是通过对映体特异性合成得到的，该合成涉及用N-三氟乙酰基保护的D-或L-丙氨酰氯对杂环核7进行酰化，然后进行酮还原和N-脱保护。对映异构体在两个受体上显示适度的立体选择性。在它们的药理研究过程中，观察到了这些新化合物类别中的一些一般趋势。对于大多数测试的光学异构体对，在5-HT（2A）和5-HT（2C）受体上，含杂环7的化合物的R-对映体仅比其S-对映体具有更高的亲和力。同样，功能研究表明，与S-对映体相比，R-对映体通常显示出更高的效价。这些芳基烷基胺的二氢呋喃环的芳香化进一步增加了亲和力和效力。仅有少数化合物是完全激动剂，其
• Crystallographic characterization of the first reported crystalline form of the potent hallucinogen (<i>R</i>)-2-amino-1-(8-bromobenzo[1,2-<i>b</i>;5,4-<i>b</i>′]difuran-4-yl)propane or `bromodragonfly': the 1:1 anhydrous proton-transfer compound with 3,5-dinitrosalicylic acid
  作者：Graham Smith、Marcus S. Cotton、Urs D. Wermuth、Sue E. Boyd

  DOI：10.1107/s0108270110012850

  日期：2010.5.15

  The 1: 1 proton-transfer compound of the potent substituted amphetamine hallucinogen (R)-2-amino-1-(8-bromobenzo[1,2-b;5,4-b']difuran-4-yl)propane (common trivial name 'bromodragonfly') with 3,5-dinitrosalicylic acid, namely 1-(8-bromobenzo[1,2-b;5,4-b']difuran-4-yl)propan-2-aminium 2-carboxy-4,6-dinitrophenolate, C13H13BrNO2+center dot C7H3N2O7-, forms hydrogen-bonded cation-anion chain substructures comprising undulating head-to-tail anion chains formed through C(8) carboxyl-nitro O-H center dot center dot center dot O associations and incorporating the aminium groups of the cations. The intrachain cation-anion hydrogen-bonding associations feature proximal cyclic R-3(3)(8) interactions involving both an N+-H center dot center dot center dot O-phenolate and the carboxyl-nitro O-H center dot center dot center dot O associations and aromatic pi-pi ring interactions [minimum ring centroid separation = 3.566 (2) angstrom]. A lateral hydrogen-bonding interaction between the third aminium H atom and a carboxyl O-atom acceptor links the chain substructures, giving a two-dimensional sheet structure. This determination represents the first of any form of this compound and is in the (R) absolute configuration. The atypical crystal stability is attributed both to the hydrogen-bonded chain substructures provided by the anions, which accommodate the aminium proton-donor groups of the cations and give crosslinking, and to the presence of the cation-anion aromatic ring pi-pi interactions.