(R)-(-)-3-(4-甲氧基苯基)-1-甲基丙胺 | 66264-83-3

• 物质功能分类: 化学试剂 - 有机试剂 - 胺盐（铵盐）
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (R)-(-)-3-(4-甲氧基苯基)-1-甲基丙胺
• 中文别名: （R）-（-）-3-（4-甲氧基-苯基）-1-甲基丙胺
• 英文名称: 4-(4-methoxyphenyl)butan-2-amine
• 英文别名: (+)-(R)-1-Methyl-3-(4-methoxyphenyl)-1-propylamine；(2R)-4-(4-methoxyphenyl)butan-2-amine
• CAS: 66264-83-3
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: JMHAKVPFYWWNOW-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  (R)-(-)-3-(4-甲氧基苯基)-1-甲基丙胺 、 (R)-2-((4-(benzyloxy)phenoxy)methyl)oxirane 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Potent, selective benzenesulfonamide agonists of the human β3 adrenergic receptor

  摘要：

  A cloned human beta(3) adrenergic receptor assay was used to identify phenoxypropanolamine agonist 1. SAR studies led to the identification of benzenesulfonamide derivative 20, a 6.3 nM beta(3) agonist which shows 30-fold selectivity for beta(3) agonist activity over beta(1) and beta(2) receptor binding. Further refinement of this lead provided 4-bromo derivative 39, a subnanomolar agonist with 660-fold and 230-fold selectivity over beta(1) and beta(2), respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00169-3
• 作为产物：
  描述：

  杜鹃醇 在 palladium on activated charcoal sodium azide 、 氢溴酸 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 16.0h， 生成 (R)-(-)-3-(4-甲氧基苯基)-1-甲基丙胺
  参考文献：
  名称：

  Betuligenol derivative with growth inhibition and antifeedant activity

  摘要：

  The title chiral amine, 3-(4-methoxyphenyl)-1-methylpropylamine 5 has been synthesized from naturally abundant betuligenol 1 in three steps and also in good yield. Furthermore, the versatile intermediate 3 could be manipulated for the preparation of chiral disulphide 7. The amine derivative 5 prepared from (-)-betuligenol showed significant growth inhibition and antifeedant activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.040

文献信息

• Enzymatic Asymmetric Synthesis of Enantiomerically Pure Aliphatic, Aromatic and Arylaliphatic Amines with (R)-Selective Amine Transaminases
  作者：Sebastian Schätzle、Fabian Steffen-Munsberg、Ahmad Thontowi、Matthias Höhne、Karen Robins、Uwe T. Bornscheuer

  DOI：10.1002/adsc.201100435

  日期：2011.9

  between pH 7.5–9. These R‐ATAs were then applied in the asymmetric synthesis of twelve aliphatic, aromatic and arylaliphatic (R)‐amines starting from the corresponding prochiral ketones using a lactate dehydrogenase/glucose dehydrogenase system to shift the equilibrium. For all ketones, at least one enzyme was found that allows complete conversion to the corresponding chiral amine having excellent optical

  最近在序列数据库中通过基于计算机的方法发现的七种（R）-选择性胺转氨酶（R-ATAs）在大肠杆菌中重组生产，并通过硫酸铵沉淀进行了部分纯化。研究了各种添加剂和各种缓冲液，以确定最佳条件，以确保生物催化过程中良好的储存稳定性和稳定的活性。所有酶在pH值7.5–9之间显示最佳的pH值。然后将这些R‐ATA用于十二种脂族，芳族和芳基脂族化合物（R）-从相应的手性酮开始，使用乳酸脱氢酶/葡萄糖脱氢酶系统转移平衡的胺。对于所有酮，发现至少一种酶可以将其完全转化为相应的手性胺，其光学纯度> 99％ee。还根据七个R-ATA之间的系统发育关系讨论了底物谱的变化。因此，我们确定了一种多功能的（R）-胺转氨酶工具箱，其在生物催化中的应用具有非凡的性能。
• Iterative Alanine Scanning Mutagenesis Confers Aromatic Ketone Specificity and Activity of L‐Amine Dehydrogenases
  作者：Xiaoqing Mu、Tao Wu、Yong Mao、Yilei Zhao、Yan Xu、Yao Nie

  DOI：10.1002/cctc.202101558

  日期：2021.12.15

  Enzyme catalysis: Protein engineering based on iterative alanine scanning mutagenesis significantly expanded the synthetically useful aromatic ketone scope of L-Bacillus cereus amine dehydrogenase. The eventual mutant (A115G/T136A/L42A/V296A/V293A) acquired after five rounds of mutagenesis successfully showed specificity toward substrates 12 a and 13 a, which have not been reported to serve as targets

  酶催化：基于迭代丙氨酸扫描诱变的蛋白质工程显着扩大了 L-蜡状芽孢杆菌胺脱氢酶的合成有用芳香酮范围。最终突变体（A115G / T136A / L42A / V296A / V293A）经过五轮诱变成功表明特异性的朝向基板获取12和13中的，还没有被报道作为由目前可用的胺脱氢酶还原胺化的目标。
• Producing optically active amino compounds
  申请人：Kaneka Corporation

  公开号：US20020192786A1

  公开（公告）日：2002-12-19

  To provide a method for preparing optically active compounds, which mainly contain (R)-amino compounds, by microbial enzymes efficiently and inexpensively; a polypeptide having stereoselective transaminase activity which can be suitably used for the above preparation method; and a DNA encoding the polypeptide. A method for preparing an optically active amino compound, characterized in stereoselectively transaminating by acting a transaminase on an amino group acceptor, a ketone compound in the presence of an amino group donor, a primary amine; a DNA comprising a nucleotide sequence encoding a polypeptide having stereoselective transaminase activity; and a polypeptide having stereoselective transaminase activity obtainable from a culture of a microorganism belonging to the genus Arthrobacter.

  提供一种通过微生物酶高效、低成本地制备主要含有(R)-氨基化合物的手段；一种具有立体选择性转氨酶活性的多肽，适用于上述制备方法；以及编码该多肽的DNA。一种制备光学活性氨基化合物的方法，其特征在于，在存在氨基供体——一种初级胺的情况下，通过作用转氨酶对氨基受体进行立体选择性转氨，将酮化合物转化为目标化合物；一种包含编码具有立体选择性转氨酶活性的多肽的核苷酸序列的DNA；以及从属于芽孢杆菌属的微生物培养物中获得的具有立体选择性转氨酶活性的多肽。
• Process for producing optically active amino compounds
  申请人：Kaneka Corporation

  公开号：US20010031487A1

  公开（公告）日：2001-10-18

  The method for preparing an optically active (R)-amino compound characterized by the method comprising stereoselectively carrying out amino group transfer by action of an (R)-form-specific transaminase in the co-presence of a ketone compound (amino acceptor), and an amino compound (amino donor) of a racemic form or an (R)-form, to give an optically active (R)-amino compound. According to the present invention, it is made possible to easily prepare at a high yield the optically active (R)-amino compounds and the like having an aryl group and the like at their 1-position, which have been conventionally difficult to prepare.

  制备光学活性(R)-氨基化合物的方法特征在于，在(R)-型特异性转氨酶的作用下，在酮化合物（氨基受体）和一个外消旋或(R)-型的氨基化合物（氨基供体）的共存下，立体选择性地进行氨基基团转移，从而获得光学活性(R)-氨基化合物。根据本发明，可以轻松高产地制备传统上难以制备的在其1-位置具有芳基等基团的光学活性(R)-氨基化合物等。
• Enantiomeric enrichment and stereoselective synthesis of chiral amines
  申请人：CELGENE CORPORATION

  公开号：EP0404146A2

  公开（公告）日：1990-12-27

  Amines in which the amino group is on a secondary car­bon atom which is chirally substituted can be enantiomeri­cally enriched by the action of an omega-amino acid transaminase which has the property of preferentially con­verting one of the two chiral forms to a ketone. The pro­cess also can be used to stereoselectively synthesize one chiral form from ketones substantially to the exclusion of the other.

  氨基位于被手性取代的仲碳原子上的胺可以通过欧米伽-氨基酸转氨酶的作用进行对映体富集，这种转氨酶具有将两种手性形式中的一种优先转化为酮的特性。该工艺还可用于从酮中立体选择性地合成一种手性形式，基本上排除另一种手性形式。