(S)-(+)-octan-2-amine hydrochloride | 61289-25-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-(+)-octan-2-amine hydrochloride
• 英文别名: (S)-(-)-2-Octanamine hydrochloride；(S)-octan-2-amine hydrochloride；(S)-2-ammoniumoctane chloride；(S)-aminooctane hydrochloride；(S)-2-amino-octane; hydro chloride；(S)-2-Amino-octan; Hydrochlord；(+)-2-Octylamine hydrochloride；(2S)-octan-2-amine;hydrochloride
• CAS: 61289-25-6
• 化学式: C₈H₁₉N*ClH
• 分子量: 165.706
• InChiKey: AXTDZHQPXGKMIB-QRPNPIFTSA-N

物化性质

• 熔点：
  85-86 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-(+)-octan-2-amine hydrochloride 、 氯甲酸三氯甲酯 在 甲烷 作用下， 以 乙酸乙酯 为溶剂， 生成 (S)-(+)-2-辛基异氰酸酯
  参考文献：
  名称：

  Histamine H3 and H4 receptor affinity of branched 3-(1H-imidazol-4-yl)propyl N-alkylcarbamates

  摘要：

  A series of imidazole-containing (non-)chiral carbamates were tested at human histamine H-3 receptor (H3R). All compounds displayed K-i values below 100 nM. A trend for a stereoselectivity at human H3R was observed for the chiral alpha-branched ligands. Selected compounds were also tested at human histamine H-4 receptor and showed moderate to weak affinities (118-1460 nM). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.005
• 作为产物：
  描述：

  N-(S)-(+)-2-octylphthalimide 在 肼 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 (S)-(+)-octan-2-amine hydrochloride
  参考文献：
  名称：

  Histamine H3 and H4 receptor affinity of branched 3-(1H-imidazol-4-yl)propyl N-alkylcarbamates

  摘要：

  A series of imidazole-containing (non-)chiral carbamates were tested at human histamine H-3 receptor (H3R). All compounds displayed K-i values below 100 nM. A trend for a stereoselectivity at human H3R was observed for the chiral alpha-branched ligands. Selected compounds were also tested at human histamine H-4 receptor and showed moderate to weak affinities (118-1460 nM). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.005

文献信息

• Sequential Reductive Amination-Hydrogenolysis: A One-Pot Synthesis of Challenging Chiral Primary Amines
  作者：Thomas C. Nugent、Daniela E. Negru、Mohamed El-Shazly、Dan Hu、Abdul Sadiq、Ahtaram Bibi、M. Naveed Umar

  DOI：10.1002/adsc.201100250

  日期：2011.8

  Difficult-to-access chiral primary amines were formed in good to high yield and ee using a rare example of a one-pot synthesis from prochiral ketones (sequential reductive amination-hydrogenloysis). As a highlight we also demonstrate a one-pot reductive amination-hydrogenolysis-reductive amination (five reactions) of ortho-methoxyacetophenone resulting in the chiral diamine 1-(2-methoxyphenyl)ethy

  以良好至高产率并且形成难以访问手性伯胺EE使用一锅合成从前手性酮的一个罕见的例子（顺序还原性胺化-hydrogenloysis）。作为亮点，我们还证明了邻甲氧基苯乙酮的一锅还原胺化-氢解还原还原胺化（五个反应）产生了手性二胺1-（2-甲氧基苯基）乙基-（2-吡啶基甲基）-胺（4）（ 58％的总收率，> 99％ee），这是一种用于水性对映选择性羟醛反应的新型有机催化剂。
• Donor Amine Salt‐Based Continuous <i>in</i>   <i>situ‐</i> Product Crystallization in Amine Transaminase‐Catalyzed Reactions
  作者：Dennis Hülsewede、Jan‐Niklas Dohm、Jan von Langermann

  DOI：10.1002/adsc.201900217

  日期：——

  The unfavorable reaction equilibrium of transaminase‐catalyzed reactions is a major challenge for the efficient biocatalytic synthesis of chiral amines. In this study the synthetic utilization of a salt‐based, continuous in situ‐product crystallization is described to overcome the thermodynamic limit in amine transaminase‐reactions using only the commonly used amine donor isopropylamine. The simultaneous

  转氨酶催化反应的不利反应平衡是有效生物催化合成手性胺的主要挑战。在这项研究中，盐基连续原位的合成利用产品结晶被描述为仅使用常用的胺供体异丙胺克服了胺转氨酶反应的热力学极限。3,3-二苯基丙酸异丙基铵（施主盐）的同时溶解与产物盐的结晶一起促进了连续胺转氨酶催化反应的热力学转变。与施加的施主盐相比，主要的工艺必要性是较低的产物盐溶解度。该概念促进了化学计量使用异丙胺与溶液中胺的浓度显着降低的组合。
• Asymmetric Intermolecular Hydroamination of Unactivated Alkenes with Simple Amines
  作者：Alexander L. Reznichenko、Hiep N. Nguyen、Kai C. Hultzsch

  DOI：10.1002/anie.201004570

  日期：2010.11.15

  A hard nut to crack: The asymmetric intermolecular Markovnikov addition of simple amines to unactivated alkenes can be achieved utilizing binaphtholate rare‐earth‐metal catalysts with up to 61 % ee and 73 % de in the case where R2 contains a stereogenic center.

  难以破解的难题：在R 2包含立体中心的情况下，可以使用双萘甲酸酯稀土金属催化剂（ee高达61％ee和de高达73％） 将简单的胺不对称分子间Markovnikov加成到未活化的烯烃上 。
• Expanding the Substrate Scope of Native Amine Dehydrogenases through <i>In Silico</i> Structural Exploration and Targeted Protein Engineering
  作者：Laurine Ducrot、Megan Bennett、Gwenaëlle André‐Leroux、Eddy Elisée、Sacha Marynberg、Aurélie Fossey‐Jouenne、Anne Zaparucha、Gideon Grogan、Carine Vergne‐Vaxelaire

  DOI：10.1002/cctc.202200880

  日期：2022.11.22

  mutation in the active site of diverse native Amine Dehydrogenases allowed to extend their substrate scope to linear aliphatic aldehydes and ketones up to C8. The structure and dynamics of these enzymes are now better understood thanks to crystal structure of the mutant and molecular dynamics studies.

  生物多样性是蛋白质工程的良好灵感来源。多种天然胺脱氢酶活性位点的靶向突变允许将其底物范围扩展到线性脂肪醛和高达 C8 的酮。由于突变体的晶体结构和分子动力学研究，现在可以更好地理解这些酶的结构和动力学。
• Step-Efficient Access to Chiral Primary Amines
  作者：Thomas Nugent、Sofiya Marinova

  DOI：10.1055/s-0032-1317589

  日期：——

  Routes to enantioenriched amines are outlined that employ reductive amination and carbanion addition methods. The strategies require either one or two reaction steps from prochiral carbonyl compounds for the synthesis of the corresponding chiral primary amines.