(S)-(+)-1-(4-methoxyphenyl)-2-benzylaminopropane | 67346-59-2

• 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-(4-methoxyphenyl)-2-benzylaminopropane
• 英文别名: (2S)-N-benzyl-1-(4-methoxyphenyl)propan-2-amine
• CAS: 67346-59-2
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: CVGPWMGXKOKNFD-AWEZNQCLSA-N

物化性质

• 沸点：
  377.8±22.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-1-(4-methoxyphenyl)-2-benzylaminopropane 在 platinum(IV) oxide 氢气 作用下， 生成 (S)-1-(3-Amino-4-benzyloxy-phenyl)-2-{benzyl-[(S)-2-(4-methoxy-phenyl)-1-methyl-ethyl]-amino}-ethanol
  参考文献：
  名称：

  Enantio- and diastereoselective synthesis of all four stereoisomers of formoterol

  摘要：

  Enantioselective syntheses of all four stereoisomers of formoterol are accomplished using asymmetric catalytic borane reductions with chiral oxazaborolidines as reducing agents. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00088-9
• 作为产物：
  描述：

  1-(4-甲氧苯基)-2-苄胺基丙烷 在 D-扁桃酸 作用下， 以 甲醇 为溶剂， 以44%的产率得到(S)-(+)-1-(4-methoxyphenyl)-2-benzylaminopropane
  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

文献信息

• METHOD FOR PRODUCING NOVEL ORGANOMETALLIC COMPLEX AND AMINE COMPOUND
  申请人：KANTO KAGAKU KABUSHIKI KAISHA

  公开号：US20160060282A1

  公开（公告）日：2016-03-03

  The purpose of the invention is to provide a novel organometallic compound that can be utilized as a catalyst having high generality, high activity, and excellent functional group selectivity. The invention pertains to a novel organometallic compound represented by general formula (1) that catalyzes a reductive amination reaction.

  该发明的目的是提供一种新型有机金属化合物，可用作具有高普适性、高活性和优异官能团选择性的催化剂。该发明涉及一种由一般式（1）表示的新型有机金属化合物，其催化还原胺化反应。
• Direct Asymmetric Reductive Amination for the Synthesis of Chiral β-Arylamines
  作者：Haizhou Huang、Xiaoyan Liu、Le Zhou、Mingxin Chang、Xumu Zhang

  DOI：10.1002/anie.201601025

  日期：2016.4.18

  The highly efficient and direct asymmetric reductive amination of arylacetones catalyzed by an iridium complex for the preparation of enantiomerically pure β‐arylamines is described. The monodentate phosphoramidite ligand exhibits superb reactivity (TONs of up to 20 000) and enantioselectivity (up to 99 % ee). Additives played important roles in this reductive coupling reaction.

  描述了一种铱络合物催化制备对映体纯的β-芳基胺的高效，直接不对称还原芳酰胺的胺化反应。单齿亚磷酰胺配体表现出极好的反应性（TONs高达20 000）和对映选择性（高达99％ee）。添加剂在该还原偶联反应中起重要作用。
• 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。
• イリジウム錯体
  申请人：日本曹達株式会社

  公开号：JP2017014195A

  公开（公告）日：2017-01-19

  【課題】本発明の目的は、工業的な触媒反応に適用し得るイリジウム錯体を提供することである。【解決手段】 下記式〔Ｉ〕で表されるイリジウム錯体。【化１】 当該イリジウム錯体の存在下に、水素供与性化合物と、イミン類を反応させて、アミン類を製造することができる。【選択図】なし

  本发明的目的是提供可应用于工业催化反应的铱配合物。解决方案是提供下述式[I]所示的铱配合物。在该铱配合物存在的情况下，可以将氢供体化合物和亚胺类化合物反应，制备胺类化合物。【选择图】无
• PREPARATION OF (R,R)-FENOTEROL AND (R,R)-OR (R,S)-FENOTEROL ANALOGUES AND THEIR USE IN TREATING CONGESTIVE HEART FAILURE
  申请人：Wainer Irving W.

  公开号：US20120157543A1

  公开（公告）日：2012-06-21

  This disclosure concerns the discovery of (R,R)- and (R,S)-fenoterol analogues which are highly effective at binding β2-adrenergic receptors. Exemplary chemical structures for these analogues are provided. Also provided are pharmaceutical compositions including the disclosed (R,R)-fenoterol and fenoterol analogues, and methods of using such compounds and compositions for the treatment of cardiac disorders such as congestive heart failure and pulmonary disorders such as asthma or chronic obstructive pulmonary disease.

  本公开涉及(R,R)-和(R,S)-芬特罗类似物的发现，它们在结合β2-肾上腺素受体方面具有高度有效性。提供了这些类似物的示例化学结构。还提供了包括所披露的(R,R)-芬特罗和芬特罗类似物的制药组合物，以及使用这些化合物和组合物治疗心脏疾病，如充血性心力衰竭和肺部疾病，如哮喘或慢性阻塞性肺疾病的方法。