(R)-(-)-2-octyl butyrate | 89378-60-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-(-)-2-octyl butyrate
• 英文别名: (R)-2-octyl butyrate；[(2R)-octan-2-yl] butanoate
• CAS: 89378-60-9
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: RBIWXCXZWBFGAA-LLVKDONJSA-N

物化性质

• 沸点：
  48-50 °C(Press: 4 Torr)
• 密度：
  0.869±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-octyl butyrate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 L-2-辛醇
  参考文献：
  名称：

  Resolution of racemic mixtures via lipase catalysis in organic solvents

  摘要：

  DOI：

  10.1021/ja00310a052
• 作为产物：
  描述：

  仲辛醇 、 2,2,2-三氯丁酸乙酯 在 porcine pancreatic lipase 作用下， 以 乙醚 为溶剂， 反应 130.0h， 以70%的产率得到(R)-(-)-2-octyl butyrate
  参考文献：
  名称：

  Resolution of racemic mixtures via lipase catalysis in organic solvents

  摘要：

  DOI：

  10.1021/ja00310a052

文献信息

• Removal of the acyl donor residue allows the use of simple alkyl esters as acyl donors for the dynamic kinetic resolution of secondary alcohols
  作者：Gerard K.M. Verzijl、Johannes G. de Vries、Quirinus B. Broxterman

  DOI：10.1016/j.tetasy.2005.02.028

  日期：2005.5

  dynamic kinetic resolution of secondary alcohols using a lipase and a ruthenium catalyst as developed by Bäckvall required some improvements to make it suitable for its use in an industrial process. The use of p-chlorophenyl acetate as acyl donor is not desirable in view of the toxicity of the side product. We herein report that simple alkyl esters can be used as acyl donors if the alcohol or ketone residue

  Bäckvall开发的使用脂肪酶和钌催化剂的仲醇动态动力学拆分方法需要进行一些改进，以使其适合工业过程使用。p的使用考虑到副产物的毒性，不希望使用乙酸-氯苯酯作为酰基供体。我们在本文中报道，如果在反应过程中连续除去在酶促酰化过程中形成的醇或酮残基，则可以将简单的烷基酯用作酰基供体。酮的添加加快了外消旋过程，使我们减少了酶和钌催化剂的用量。探索了该方法的范围，并找到了合适范围的酰基供体。使用丁酸异丙酯或苯乙酸甲酯作为酰基供体，使各种苄醇和脂肪醇反应，在大多数情况下，酯的收率> 95％，ee分离为99％。此外，
• Efficient dynamic kinetic resolution of secondary alcohols with a novel tetrafluorosuccinato ruthenium complex
  作者：Sjoerd F.G.M. van Nispen、Jeroen van Buijtenen、Jef A.J.M. Vekemans、Jan Meuldijk、Lumbertus A. Hulshof

  DOI：10.1016/j.tetasy.2006.08.003

  日期：2006.9

  Dynamic kinetic resolution (DKR) of a series of secondary alcohols has been conducted with a novel dinuclear ruthenium complex, bearing tetrafluorosuccinate and (rac)-BINAP ligands as the racemization catalyst. Novozym 435 has been used as the enzyme, and isopropyl butyrate as the acyl donor. Five substrates underwent DKR successfully: an aliphatic and an aromatic secondary alcohol, an aromatic alcohol

  已经用新型的双核钌配合物进行了一系列仲醇的动态动力学拆分（DKR），该配合物带有四氟琥珀酸酯和（rac）-BINAP配体作为外消旋催化剂。已将Novozym 435用作酶，并将丁酸异丙酯用作酰基供体。五个基材成功进行了DKR：脂族和芳族仲醇，在苯环上带有吸电子取代基的芳族醇，在环上带有给电子取代基的芳族醇和杂芳族仲醇。催化剂在70°C时表现最佳。通常，相对于底物，用0.1mol％的外消旋催化剂，反应在1天内达到完全转化。对应于底物的酮的添加稳定了活性Ru络合物，因此增加了反应速率。
• Process for producing an optically active alcohol by a biochemical method
  申请人：Chisso Corporation

  公开号：EP0231089A2

  公开（公告）日：1987-08-05

  Optically active alcohols represented by the formula: wherein X indicates an alkyl group having a carbon number of 2-10, Y indicates an alkyl group having a carbon number of 1-3, CF3 or CN, and X ≠ Y, have optical isomers, so that these alcohols do not sufficiently exhibit activity in many cases unless either R- or S-alcohol is purely contained. The production of the pure R- or S-alcohol was restricted to a few methods, so it is desired to develop a method for optically resolving of the secondary alcohols by an industrially advantageous method. This invention comprises using a particular enzyme having the ability to conduct preferentially a transesterification reaction with a triglyceride and an (R, S)-alcohol represented by the above formula and the triglyceride to conduct the transesterification reaction under substantially anhydrous conditions and resolving the resulting ester to obtain an optically active alcohol which contains richly either R- or S-alcohol.

  由式表示的光学活性醇： 其中 X 表示碳原子数为 2-10 的烷基，Y 表示碳原子数为 1-3 的烷基、CF3 或 CN，且 X≠Y 具有光学异构体，因此在许多情况下，除非纯粹含有 R-或 S-醇，否则这些醇不能充分显示出活性。纯 R-或 S-醇的生产仅限于少数几种方法，因此，人们希望开发一种在工业上有利的方法，对仲醇进行光学解析。 本发明包括使用一种特殊的酶，该酶具有优先与甘油三酯和由上式表示的（R，S）醇进行酯交换反应的能力，并使用甘油三酯在基本上无水的条件下进行酯交换反应，并解析所得到的酯，以获得光学活性醇，该醇富含 R-或 S-醇。
• Process for the preparation of enantiomerically enriched esters and alcohols
  申请人：——

  公开号：US20040077059A1

  公开（公告）日：2004-04-22

  Method for the preparation of an enantiomerically enriched ester, in which a mixture of the enantiomers of the corresponding secondary alcohol is subjected, in the presence of an acyl donor, to an enantioselective conversion in the presence of a racemisation catalyst upon which the ester is formed and an acyl donor residue is obtained, and in which the acyl donor residue is irreversibly removed from the phase in which the enantioselective conversion takes place. Preferably the enantioselective conversion is carried out enzymatically and a transfer hydrogenation catalyst is used as racemisation catalyst. The secondary alcohol can be formed in situ from the corresponding ketone, in the presence of a hydrogen donor. It is also possible to use a mixture of the secondary alcohol and the corresponding ketone as substrate. Preferably the acyl donor is chosen so that the acyl donor residue is converted in situ into another compound and/or the acyl donor residue is removed via distillation under reduced pressure. The enantiomerically enriched esters obtained can subsequently be converted into the corresponding enantiomerically enriched alcohols, which are desirable intermediate products in the preparation of liquid crystals, agro chemicals or pharmaceuticals.

  制备对映体富集酯的方法，在该方法中，相应仲醇的对映体混合物在酰基供体存在下，在消旋化催化剂存在下进行对映体选择性转化，在此过程中形成酯并获得酰基供体残留物，酰基供体残留物不可逆转地从进行对映体选择性转化的相中移除。最好用酶法进行对映选择性转化，并使用转移氢化催化剂作为消旋化催化剂。 在氢供体存在的情况下，仲醇可由相应的酮原位生成。也可以使用仲醇和相应酮的混合物作为底物。 最好选择酰基供体，以便酰基供体残留物就地转化为另一种化合物和/或通过减压蒸馏除去酰基供体残留物。 获得的对映体富集酯随后可转化为相应的对映体富集醇，这些醇是制备液晶、农用化学品或药物的理想中间产品。
• Preparative production of optically active esters and alcohols using esterase-catalyzed stereospecific transesterification in organic media
  作者：Bernard Cambou、Alexander M. Klibanov

  DOI：10.1021/ja00321a033

  日期：1984.5