(R)-octan-2-yl propionate | 116907-37-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-octan-2-yl propionate
• 英文别名: [(2R)-octan-2-yl] propanoate
• CAS: 116907-37-0
• 化学式: C₁₁H₂₂O₂
• 分子量: 186.294
• InChiKey: AJJGEXYNDGEAQF-SNVBAGLBSA-N

物化性质

• 沸点：
  214.2±8.0 °C(Predicted)
• 密度：
  0.870±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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)-octan-2-yl propionate 在 sodium hydroxide 作用下， 反应 4.0h， 生成 L-2-辛醇
  参考文献：
  名称：

  Anhydrides as acylating agents in lipase-catalyzed stereoselective esterification of racemic alcohols

  摘要：

  DOI：

  10.1021/jo00258a024
• 作为产物：
  描述：

  1-辛炔 在 C₃₈H₄₆O₃P₂*C₇H₈*Rh⁽¹⁺⁾*BF₄^(1-) 、 氢气 、 钌 作用下， 以 二氯甲烷 、 水 为溶剂， 40.0~60.0 ℃ 、400.01 kPa 条件下， 反应 48.0h， 生成 (R)-octan-2-yl propionate
  参考文献：
  名称：

  1-烷基乙烯基苯甲酸酯的高度对映选择性加氢：手性2-烷基醇的简单，非酶促途径

  摘要：

  走向手性！描述了通过使用带有P bearingOP配体的Rh催化剂对烯醇酯1的高度对映选择性催化氢化（参见方案； NBD ＝降冰片二烯）。该催化体系具有广泛的范围，并允许制备具有高对映选择性的各种带有各种烷基或苄基的手性酯2。这些酯可以很容易地转化为高度对映体富集的2-链烷醇。

  DOI：

  10.1002/chem.201303500

文献信息

• Dynamic Double Kinetic Resolution of Amines and Alcohols under the Cocatalysis of Raney Nickel/<i>Candida antarctica</i>Lipase B: From Concept to Application
  作者：Bo Xia、Guilin Cheng、Xianfu Lin、Qi Wu

  DOI：10.1002/ejoc.201400042

  日期：2014.5

  Herein, we have established a dynamic double kinetic resolution (DDKR) strategy under the co-catalysis of Raney nickel and Candida antarctica lipase B (CAL-B) for the one-pot simultaneous resolution of primary amines and secondary alcohols (or esters). The DDKR strategy was successfully applied to the resolution of a series of racemic amines and secondary alcohols (or esters) as well as mexiletine, an

  在此，我们建立了在雷尼镍和南极念珠菌脂肪酶 B (CAL-B) 共催化下的动态双动力学拆分 (DDKR) 策略，用于一锅同时拆分伯胺和仲醇（或酯）。DDKR 策略已成功应用于一系列外消旋胺和仲醇（或酯）以及美西律（一种重要的抗心律失常药）的拆分。催化剂可以重复使用多次，并具有相同的高活性。放大实验也很成功。作为比传统的简单动力学拆分更原子经济和更有效的方法，DDKR 策略可广泛用于制备光学纯的胺和醇。
• 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。
• Asymmetric Hydrogenation of 1-Alkyl and 1-Aryl Vinyl Benzoates: A Broad Scope Procedure for the Highly Enantioselective Synthesis of 1-Substituted Ethyl Benzoates
  作者：Patryk Kleman、Pedro J. González-Liste、Sergio E. García-Garrido、Victorio Cadierno、Antonio Pizzano

  DOI：10.1021/cs501402z

  日期：2014.12.5

  The enantioselective hydrogenation of enol esters of formula CH2=C(OBz)R with rhodium catalysts based on phosphine phosphite ligands (P-OP) has been studied. The reaction has a broad scope, and it is suitable for the preparation of products possessing a wide variety of R substituents. For the cases where R is a primary alkyl, high catalyst activity (S/C = 500) and enantioselectivities (95-99% ee) were obtained with a catalyst characterized by an ethane backbone and a PPh2 fragment. In contrast, for R = t-Bu, a catalyst possessing a benzene backbone provided the best results (97% ee). Derivatives with a cycloalkyl R substituent were particularly difficult substrates for this reaction. A broader catalyst screening was required for these substrates, which identified a catalyst possessing a P(m-xylyl)(2) fragment as the most appropriate one, affording enantioselectivities between 90 and 95% ee. Outstanding enantioselectivities (99% ee) and high catalyst activity (S/C = 500-1000) were also obtained in the case of substrates bearing a Ph or a fluoroaryl R substituent. In addition, the system is also appropriate for the preparation of other synthetically useful esters as those for R = benzyl, 2-phenylethyl or N-phthalimido alkyl chains. Likewise, the hydrogenation of divinyl dibenzoates proceeded with very high diastero- and enantioselectivity, generating rather low amounts of the meso isomer (3-6%). On the other hand, substrates with Br and MeO substituents at the phenyl benzoate ring, suitable for further functionalization, have also been examined. The results obtained indicate no detrimental effect of these substituents in the hydrogenation. Alternatively, the methodology has been applied to the highly enantioselective synthesis of deuterium isotopomers of 1-octyl benzoate bearing CDH2, CD2H, or CD3 fragments. Finally, as a practical advantage of the present system, it has been observed that the high performance of the catalysts is retained in highly concentrated solutions or even in the neat substrate, minimizing both the amount of solvent added and the volume of the reaction.
• Activity enhancement of pig liver esterase in organic solvents by colyophilization with methoxypolyethylene glycol: kinetic resolution of alcohols
  作者：Stephan Ruppert、Hans-Joachim Gais

  DOI：10.1016/s0957-4166(97)00469-2

  日期：1997.11

  Colyophilization of pig liver esterase with methoxypolyethylene glycol gave a catalyst, PLE/MPEG, which showed an enhanced activity in organic solvents. The PLE/MPEG catalyzed transesterification of the alcohols rac-1a-d with vinyl propionate in toluene proceeded with good to high selectivities. The addition of up to 1% of water to the reaction mixture resulted in a significant increase in enantioselectivity. Immobilization of PLE/MPEG for the batch-wise resolution was accomplished by its spontaneous adsorption on an ultrafiltration membrane. (C) 1997 Elsevier Science Ltd.
• BIANCHI, DANIELE;CESTI, PIETRO;BATTISTEL, EZIO, J. ORG. CHEM., 53,(1988) N3, C. 5531-5534
  作者：BIANCHI, DANIELE、CESTI, PIETRO、BATTISTEL, EZIO

  DOI：——

  日期：——