(R)-6-amino-2-methylheptan-2-ol | 165962-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-6-amino-2-methylheptan-2-ol
• 英文别名: (6R)-6-amino-2-methylheptan-2-ol
• CAS: 165962-54-9
• 化学式: C₈H₁₉NO
• 分子量: 145.245
• InChiKey: LREQLEBVOXIEOM-SSDOTTSWSA-N

物化性质

• 沸点：
  250.1±13.0 °C(Predicted)
• 密度：
  0.895±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-6-amino-2-methylheptan-2-ol 在 2,2,2-三氟乙硫醇 作用下， 以 四氢呋喃 、 3-甲基-3-戊醇 为溶剂， 反应 2.0h， 生成 6-氨基-2-甲基-2-庚醇
  参考文献：
  名称：

  En Route to (S)-Selective Chemoenzymatic Dynamic Kinetic Resolution of Aliphatic Amines. One-Pot KR/Racemization/KR Sequence Leading to (S)-Amides

  摘要：

  A one-pot sequential process, involving a radical racemization and an enzymatic resolution, provides access to (S)-amides, from racemic amines, with ee and yields ranging from 78 to 94% and 58 to 80%, respectively.

  DOI：

  10.1021/jo900074w
• 作为产物：
  描述：

  6-氨基-2-甲基-2-庚醇 在 Candida antarctica lipase B 作用下， 以 正庚烷 为溶剂， 反应 72.0h， 生成 (S)-6-amino-2-methylheptan-2-ol 、 (R)-6-amino-2-methylheptan-2-ol
  参考文献：
  名称：

  在30°C下高效光化学诱导的硫胺基自由基介导的脂肪胺消旋

  摘要：

  在30°C的温和条件下，在硫醇的存在下进行UV辐照可实现高效脂肪族胺的消旋化。该反应通过前手性α-氨基烷基自由基的可逆生成而进行。后者可能是由于噻吩基和胺之间的氧化还原过程或由噻吩基直接提取氢原子引起的。作为氢原子供体，硫醇起着至关重要的作用。虽然伯胺和仲胺的外消旋都是快速的过程，但叔胺的外消旋却很缓慢。暂定原理是基于光刺激的胺催化的硫醇氧化成相应的二硫化物，这使得反应介质中氢原子供体的浓度以取决于胺的性质的速率下降至痕量。

  DOI：

  10.1021/jo702241y

文献信息

• N-Acyl glycinates as acyl donors in serine protease-catalyzed kinetic resolution of amines. Improvement of selectivity and reaction rate
  作者：Malek Nechab、Lahssen El Blidi、Nicolas Vanthuyne、Stéphane Gastaldi、Michèle P. Bertrand、Gérard Gil

  DOI：10.1039/b812089g

  日期：——

  Enzymatic kinetic resolution of aliphatic and benzylic amines leading to (S)-amides was achieved by using alkaline protease as the catalyst and N-octanoyl glycine trifluoroethyl ester as the acyl donor; enantioselectivity ranged between 4 to 244, while reaction times were dramatically shortened and ranged between 15 min to 6 h.

  通过使用碱性蛋白酶作为催化剂，N-辛酰基甘氨酸三氟乙基酯作为酰基供体，可以实现脂肪族和苄基胺类的酶动力学拆分，从而生成（S）-酰胺。对映选择性在4至244之间，而反应时间则大大缩短，在15分钟至6小时之间。
• N-Octanoyldimethylglycine Trifluoroethyl Ester, an Acyl Donor Leading to Highly Enantioselective Protease-Catalysed Kinetic Resolution of Amines
  作者：Severine Queyroy、Nicolas Vanthuyne、Stéphane Gastaldi、Michèle P. Bertrand、Gérard Gil

  DOI：10.1002/adsc.201100993

  日期：2012.6.18

  The use of N‐octanoyldimethylglycine trifluoroethyl ester as acyl donor in the kinetic resolution of aliphatic amines catalysed by proteases led to enantiomeric ratios >200 in most cases. The resolutions mediated by Protex 6L were shown to be much faster than the resolutions achieved with the most efficient commercially available serine proteases, i.e., alkaline protease, Properase 1600L, and Subtilisin

  在大多数情况下，在蛋白酶催化的脂肪族胺的动力学拆分中，使用N-辛酰基二甲基甘氨酸三氟乙基酯作为酰基供体会导致对映体比率> 200。已证明，由Protex 6L介导的分辨率比使用最有效的市售丝氨酸蛋白酶（即碱性蛋白酶，Properase 1600L和枯草杆菌蛋白酶）获得的分辨率快得多。
• [EN] PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED AMINES<br/>[FR] PROCEDE DE PREPARATION D'AMINES ENANTIOMERIQUEMENT ENRICHIES
  申请人：DSM NV

  公开号：WO2002020821A2

  公开（公告）日：2002-03-14

  Process for the preparation of an enantiomerically enriched acylated amine, wherein an enantiomerically enriched, substituted or unsubstituted phenylglycine amide is contacted with a mixture of enantiomers of the corresponding amine H2NCR1R2R3 where R1, R2 and R3 are not the same and each independently stands for H, CN, a substituted (cyclo)alkyl group, aryl group, alkylaryl group or arylalkyl group, a cyclic or non-cyclic heteroaryl group or heteroaryl group with one or more N, O of S atoms or (CH2)n-COR4, where n=0, 1 ...6 and R4 is OH or a substituted or unsubstituted alkyl group, aryl group, alkoxy group or amino group or where R1 and R2 (and R3) together with the C atom to which they are bound form a (bi)cyclic group which may or may not contain one or more N, O of S atoms, in the presence of a Pen-G acylase. A process for the preparation of enantiomerically enriched amine with formula H2NCR1R2R3 where R1, R2 and R3 are as defined above, wherein an acylated amine is contacted with a Pen-G acylase. Preferably a Pen-G acylase derived from Alcaligenes faecalis is applied.
• En Route to (<i>S</i>)-Selective Chemoenzymatic Dynamic Kinetic Resolution of Aliphatic Amines. One-Pot KR/Racemization/KR Sequence Leading to (<i>S</i>)-Amides
  作者：Lahssen El Blidi、Malek Nechab、Nicolas Vanthuyne、Stéphane Gastaldi、Michèle P. Bertrand、Gérard Gil

  DOI：10.1021/jo900074w

  日期：2009.4.3

  A one-pot sequential process, involving a radical racemization and an enzymatic resolution, provides access to (S)-amides, from racemic amines, with ee and yields ranging from 78 to 94% and 58 to 80%, respectively.
• Highly Efficient Photochemically Induced Thiyl Radical-Mediated Racemization of Aliphatic Amines at 30 °C
  作者：Lucie Routaboul、Nicolas Vanthuyne、Stéphane Gastaldi、Gérard Gil、Michèle Bertrand

  DOI：10.1021/jo702241y

  日期：2008.1.1

  performance of highly efficient aliphatic amines racemization, under mild conditions at 30 °C. The reaction proceeds via the reversible generation of prochiral α-aminoalkyl radicals. The latter may result either from a redox process between the thiyl radical and the amine or from direct hydrogen atom abstraction by thiyl radical. As hydrogen atom donor, the thiol plays a crucial role. While the racemization

  在30°C的温和条件下，在硫醇的存在下进行UV辐照可实现高效脂肪族胺的消旋化。该反应通过前手性α-氨基烷基自由基的可逆生成而进行。后者可能是由于噻吩基和胺之间的氧化还原过程或由噻吩基直接提取氢原子引起的。作为氢原子供体，硫醇起着至关重要的作用。虽然伯胺和仲胺的外消旋都是快速的过程，但叔胺的外消旋却很缓慢。暂定原理是基于光刺激的胺催化的硫醇氧化成相应的二硫化物，这使得反应介质中氢原子供体的浓度以取决于胺的性质的速率下降至痕量。