(S)-(+)-1-phenyl-2-benzylaminopropane | 15062-72-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(+)-1-phenyl-2-benzylaminopropane
• 英文别名: (S)-N-benzyl-1-phenylpropan-2-amine；N-Demethylbenzphetamine；(2S)-N-benzyl-1-phenylpropan-2-amine
• CAS: 15062-72-3
• 化学式: C₁₆H₁₉N
• 分子量: 225.334
• InChiKey: JLCDKDGHTWGGQM-AWEZNQCLSA-N

物化性质

• 沸点：
  339.0±11.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-(+)-1-phenyl-2-benzylaminopropane 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 120.0 ℃ 、344.75 kPa 条件下， 反应 44.0h， 生成 5-[(R)-1-hydroxy-2-((S)-1-methyl-2-phenylethylamino)ethyl]-1,3-benzenediol
  参考文献：
  名称：

  Comparative Molecular Field Analysis of the Binding of the Stereoisomers of Fenoterol and Fenoterol Derivatives to the β₂ Adrenergic Receptor

  摘要：

  Stereoisomers of fenoterol and six fenoterol derivatives have been synthesized and their binding affinities for the beta(2) adrenergic receptor (K-i beta(2)-AR), the subtype selectivity relative to the beta(1)-AR (K-i beta(1)-AR/K-i beta(2)-AR) and their functional activities were determined. Of the 26 compounds synthesized in the study, submicromolar binding affinities were observed for (R,R)-fenoterol, the (R,R)-isomer of the p-methoxy, and (R,R)- and (R,S)-isomers of 1-naphthyl derivatives and all of these compounds were active at submicromolar concentrations in cardiomyocyte contractility tests. The K-i beta(1)-AR/K-i beta(2)-AR ratios were > 40 for (R,R)-fenoterol and the (R,R)-p-methoxy and (R,S)-1-naphthyl derivatives and 14 for the (R,R)-1-napthyl derivative. The binding data was analyzed using comparative molecular field analysis (CoMFA), and the resulting model indicated that the fenoterol derivatives interacted with two separate binding sites and one steric restricted site on the pseudo-receptor and that the chirality of the second stereogenic center affected K-i beta(2) and subtype selectivity.

  DOI：

  10.1021/jm070030d
• 作为产物：
  描述：

  D-苯丙氨酸 在 sodium tetrahydroborate 、 硫酸 、 三乙胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 71.0h， 生成 (S)-(+)-1-phenyl-2-benzylaminopropane
  参考文献：
  名称：

  一种盐酸苄非他明的制备方法

  摘要：

  本发明涉及化学制药领域，具体涉及盐酸苄非他明的制备方法。本发明方法避免了使用麻黄碱、伪麻黄碱、脱氧麻黄碱等管控品；本发明的原料廉价易得，降低了合成成本。使用本发明制备方法，可以高收率得到高纯度的目标化合物，易于工业化的大规模生产。

  公开号：

  CN110668952B

文献信息

• Hair Analysis for Drugs of Abuse. XI. Disposition of Benzphetamine and Its Metabolites into Hair and Comparison of Benzphetamine Use and Methamphetamine Use by Hair Analysis.
  作者：Ruri KIKURA、Yuji NAKAHARA

  DOI：10.1248/bpb.18.1694

  日期：——

  In order to study the disposition of benzphetamine (BZP) and its metabolites, desmethyl benzphetamine (norBZP), p-hydroxy desmethyl benzphetamine (OHnorBZP), methamphetamine (MA) and amphetamine (AP), from plasma to hair in rats, an analytical method for identifying these drugs in plasma, urine and hair was developed with selected ion monitoring of gas chromatograph/mass spectrometry (GC/MS-SIM) results. After the intraperitoneal administration of BZP to rats (10 mg/kg/d, 10d, n=3), concentrations of BZP and its metabolites in rat hair newly grown for 4 weeks were compared to the areas under the concentration versus time curve (AUCs) of these drugs in the rat plasma. The concentrations of BZP, norBZP, OHnorBZP, MA and AP in the rat hair were 14.8±1.4, 6.1±0.3, 2.6±0.5, 2.3±0.1 and 9.2±0.3 ng/mg, and the ratio of the concentrations in the hair to AUCs in the rat plasma was 3.0 : 0.1 : 0.1 : 0.6 : 0.2, respectively. This fact suggested that BZP tends to be readily incorporated into hair from blood. The method was applied to the determination of the metabolites in scalp hair and pubic hair of humans who orally ingested BZP (30 mg/d, 5d, n=2). BZP, norBZP, MA and AP were detected at 0.14-0.56, 0.29-0.63, 0.10 and 1.06-1.66 ng/mg in the scalp hair and at 0.10-0.20, 0.13-0.18, trace-0.15 and 0.23 ng/mg in the pubic hair, respectively. It was shown that BZP use could be retrospectively distinguished from MA use by the detection of BZP and/or norBZP in hair.

  为了研究苯丙甲庚嗪(BZP)及其代谢物去甲基苯丙甲庚嗪(norBZP)、对羟基去甲基苯丙甲庚嗪(OHnorBZP)、甲基苯丙胺(MA)和苯丙胺(AP)从大鼠血浆到毛发的转运情况，开发了一种分析方法，采用气相色谱/质谱选择离子监测(GC/MS-SIM)结果来鉴定血浆、尿液和毛发中的这些药物。在大鼠腹腔注射BZP(10 mg/kg/d, 10d, n=3)后，比较了新生长4周的大鼠毛发中BZP及其代谢物的浓度与大鼠血浆中这些药物的浓度-时间曲线下面积(AUCs)。大鼠毛发中BZP、norBZP、OHnorBZP、MA和AP的浓度分别为14.8±1.4、6.1±0.3、2.6±0.5、2.3±0.1和9.2±0.3 ng/mg，毛发浓度与大鼠血浆AUCs的比率为3.0 : 0.1 : 0.1 : 0.6 : 0.2。这一事实表明，BZP倾向于从血液中容易地进入毛发。该方法应用于测定口服摄入BZP(30 mg/d, 5d, n=2)的人的头皮毛发和阴毛中的代谢物。在头皮毛发中检测到BZP、norBZP、MA和AP的浓度分别为0.14-0.56、0.29-0.63、0.10和1.06-1.66 ng/mg，而在阴毛中分别为0.10-0.20、0.13-0.18、痕量-0.15和0.23 ng/mg。结果表明，通过检测毛发中的BZP和/或norBZP，可以回顾性地区分BZP使用和MA使用。
• 盐酸苄非他明的制备方法
  申请人：安徽贝克制药股份有限公司

  公开号：CN110655466B

  公开（公告）日：2023-02-24

  本发明涉及化学制药领域，具体涉及盐酸苄非他明（Benzphetamine Hydrochloride）的制备方法。本发明方法避免了使用麻黄碱、伪麻黄碱、脱氧麻黄碱等管控品；本发明的原料廉价易得，降低了合成成本；使用本发明制备方法，可以高收率得到高纯度的目标化合物，易于工业化的大规模生产。
• Rh‐Catalyzed Asymmetric Hydrogenation of α,β‐ and β,β‐Disubstituted Unsaturated Boronate Esters
  作者：Qiaozhi Yan、Xin Shen、Guofu Zi、Guohua Hou

  DOI：10.1002/chem.202000703

  日期：2020.5.12

  A highly enantioselective hydrogenation of α,β-unsaturated boronate esters catalyzed by Rh-(S)-DTBM-Segphos complex has been developed. Both (Z)-α,β- and β,β-disubstituted substrates can be successfully hydrogenated to afford chiral boronates with excellent enantioselectivities, up to 98 % ee. Furthermore, the obtained chiral boronate esters, as important versatile synthetic intermediates are successfully

  已经开发了由Rh-（S）-DTBM-Segphos络合物催化的α，β-不饱和硼酸酯的高度对映选择性氢化。（Z）-α，β-和β，β-二取代的底物都可以成功氢化，以提供具有优异对映选择性（最高ee为98％）的手性硼酸酯。此外，将获得的手性硼酸酯作为重要的通用合成中间体成功地转化为相应的手性醇，胺和其他重要的具有对映选择性的重要衍生物。
• DUAL CHARGING SYSTEM FOR SELECTIVELY INTRODUCING NON-NATIVE AMINO ACIDS INTO PROTEINS USING AN IN VITRO SYNTHESIS METHOD
  申请人：Voloshin Alexei M.

  公开号：US20100184134A1

  公开（公告）日：2010-07-22

  This invention provides for a novel means of incorporating non-native amino acids into preselected positions of a protein using a cell-free synthesis system. The methods involve the use of non-orthogonal, native isoaccepting sense tRNAs that are encoded by the genetic code. Such methods allow for numerous non-native amino acids to be incorporated through the use of sense codons without having to rely upon orthogonal tRNA-synthetase pairs.

  这项发明提供了一种新的方法，利用无细胞合成系统将非天然氨基酸并入蛋白质的预选位点。该方法涉及使用非正交的、由遗传密码编码的本地同义tRNA，以实现通过使用同义密码子并不依赖于正交tRNA合成酶对的情况下并入多种非天然氨基酸的目的。
• MONO CHARGING SYSTEM FOR SELECTIVELY INTRODUCING NON-NATIVE AMINO ACIDS INTO PROTEINS USING AN IN VITRO PROTEIN SYNTHESIS SYSTEM
  申请人：Voloshin Alexei M.

  公开号：US20100184135A1

  公开（公告）日：2010-07-22

  This invention provides for a novel means of incorporating non-native amino acids into preselected positions of a protein using a cell-free synthesis system. The methods involve the use of non-orthogonal, native isoaccepting sense tRNAs that are encoded by the genetic code. Such methods allow for numerous non-native amino acids to be incorporated through the use of sense codons without having to rely upon orthogonal tRNA-synthetase pairs.

  这项发明提供了一种新颖的方法，利用无细胞合成系统将非天然氨基酸纳入蛋白质的预选位点。该方法涉及使用由基因密码编码的非正交、本地同义tRNA，这些tRNA可接受相同的氨基酸。这种方法允许通过使用同义密码子纳入许多非天然氨基酸，而无需依赖正交tRNA合成酶对。