(-)-2-(4-isobutylphenyl)-1-acetoxypropane | 194606-27-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-2-(4-isobutylphenyl)-1-acetoxypropane
• 英文别名: (S)-2-(4-isobutyl-phenyl)-1-acetoxy-propane；[(2S)-2-[4-(2-methylpropyl)phenyl]propyl] acetate
• CAS: 194606-27-4
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: GHSPRSYYTJESSJ-GFCCVEGCSA-N

物化性质

• 沸点：
  310.7±11.0 °C(Predicted)
• 密度：
  0.967±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (-)-2-(4-isobutylphenyl)-1-acetoxypropane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到(S)-2-(4-isobutylphenyl)propan-1-ol
  参考文献：
  名称：

  Lipase-mediated asymmetric construction of 2-arylpropionic acids: enantiocontrolled syntheses of S-naproxen and S-ibuprofen

  摘要：

  A general and enantiocontrolled synthetic route to 2-arylpropionic acids, represented by non-steroidal anti-inflammatory drugs S-naproxen 1a and S-ibuprofen 1b, has been developed by employing the lipase-mediated asymmetric acetylation of prochiral 2-aryl-1,3-propanediol 3, which has been derived via a Heck reaction, as the key step. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00237-1
• 作为产物：
  描述：

  异丁基苯 在 4-二甲氨基吡啶 、 palladium diacetate 、 sodium tetrahydroborate 、 Barluenga reagent 、 三氟甲磺酸 、 臭氧 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 lipase 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.5h， 生成 (-)-2-(4-isobutylphenyl)-1-acetoxypropane
  参考文献：
  名称：

  Lipase-mediated asymmetric construction of 2-arylpropionic acids: enantiocontrolled syntheses of S-naproxen and S-ibuprofen

  摘要：

  A general and enantiocontrolled synthetic route to 2-arylpropionic acids, represented by non-steroidal anti-inflammatory drugs S-naproxen 1a and S-ibuprofen 1b, has been developed by employing the lipase-mediated asymmetric acetylation of prochiral 2-aryl-1,3-propanediol 3, which has been derived via a Heck reaction, as the key step. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00237-1

文献信息

• Process for the enzymatic separation of the optical isomers of racemic
  申请人：Istituto Guido Donegani S.p.A.

  公开号：US04980291A1

  公开（公告）日：1990-12-25

  Biotechnological resolution by means of enzymatic transesterification of the relevant racemic mixture of the optical isomers of .alpha.-alkyl-substituted primary alcohols having the formula (I): ##STR1## wherein: R represents a linear or branched (C.sub.1 -C.sub.20)-alkyl or alkenyl group or an aryl group, also substituted or condensed with other groups, in particular a group of formula (II) or (III): ##STR2## wherein: R.sup.ii represents a (C.sub.1 -C.sub.8)-alkyl group, a (C.sub.1 -C.sub.4)-alkenyl group, an alkoxy, phenyl, phenoxy, benzoyl, or heterocyclic group; R.sup.iii represents a hydrogen or halogen atom; R.sup.iv represents a (C.sub.1 -C.sub.4)-alkyl group, and wherein R.sup.i represents a (C.sub.1 -C.sub.4)-alkyl group either equal to, or different from, R, in the presence of an enzyme either free or immobilized on a support capable of selectively causing the S isomer to be esterified, with the R isomer being left substantially unchanged, said isomers being then separated according to techniques known from the prior art. The process is used in the synthesis of antiinflammatory agents.

  通过酶催化转酯化技术对具有以下式子（I）的.alpha.-烷基取代一级醇的相关外消旋混合物进行生物技术分离，其中：R代表线性或支链（C.sub.1-C.sub.20）-烷基或烯基基团或芳基基团，也可被其他基团取代或缩合，特别是式子（II）或（III）的基团：##STR2## 其中：R.sup.ii代表（C.sub.1-C.sub.8）-烷基，（C.sub.1-C.sub.4）-烯基，烷氧基，苯基，苯氧基，苯甲酰基或杂环基团；R.sup.iii代表氢或卤素原子；R.sup.iv代表（C.sub.1-C.sub.4）-烷基。其中，R.sup.i代表（C.sub.1-C.sub.4）-烷基，与R相同或不同。在酶自由或固定在支持体上的存在下，能够选择性地使S异构体酯化，而R异构体基本不变，然后根据先前技术的技术进行分离。该过程用于抗炎药物的合成。
• Differences in reactivity and enantioselectivity in lipase reactions with carboxylic esters and alcohols bearing the same stereogenic center
  作者：John C Sih、Rui Lin Gu

  DOI：10.1016/0957-4166(95)00012-e

  日期：1995.2

  The reaction rate and stereochemical outcome of lipase reactions obtained with carboxylic esters and alcohols, which contain the same stereogenic center, can be modulated by changing the mode of the lipase reaction, i.e. ester hydrolysis versus alcohol acetylation.
• US4980291A
  申请人：——

  公开号：US4980291A

  公开（公告）日：1990-12-25