(R)-1-(cyanomethyl)propyl acetate | 198561-46-5

• 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)-1-(cyanomethyl)propyl acetate
• 英文别名: (R)-1-cyanobutan-2-yl acetate；[(2R)-1-cyanobutan-2-yl] acetate
• CAS: 198561-46-5
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: JCVZTBWPZRMHQT-SSDOTTSWSA-N

物化性质

• 沸点：
  228.1±23.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-(cyanomethyl)propyl acetate 在 Pseudomonas ceracia lipase 、 水 作用下， 以 丙酮 为溶剂， 生成 (R)-3-羟基戊腈
  参考文献：
  名称：

  硫冠醚添加剂对脂肪酶催化反应的非对映选择性的影响：通过双酶促反应策略制备光学活性 3-羟基-2-甲基链烷腈

  摘要：

  已经研究了对脂肪酶催化水解 3-羟基-2-甲基-或 3-羟基-2-乙基链烷腈的乙酸酯的非对映选择性的累加效应。尽管观察到对映选择性的显着改变，但非对映选择性不受硫冠醚添加剂的影响。因此，脂肪酶催化反应的非对映选择性的起源明显不同于对映选择性的起源。基于这些结果，通过双酶促反应策略通过脂肪酶催化反应证明了光学活性 3-羟基-2-甲基戊腈和 3-羟基-2-甲基丁腈的简单制备。

  DOI：

  10.1246/bcsj.72.1589
• 作为产物：
  描述：

  (R)-1-(cyanomethyl)propyl butyrate 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲基叔丁基醚 为溶剂， 反应 29.0h， 生成 (R)-1-(cyanomethyl)propyl acetate
  参考文献：
  名称：

  通过酶促还原并随后通过脂肪酶催化的酯水解提高光学纯度，有效制备对映体过量高的（R）-3-羟基戊腈。

  摘要：

  成功建立了使用两种酶促反应合成超过99％对映体过量的（R）-3-羟基戊腈（1）的有效化学酶促程序。用还原酶S1对3-氧戊烯腈进行初始对映选择性酶促还原，得到具有81.5％ee的（R）-1，然后将其转化为正丁酸（R）-1-（氰甲基）丙基（3b）。随后的脂肪酶催化3b的对映选择性水解以高收率（超过99％ee）得到（R）-1。

  DOI：

  10.1271/bbb.120331

文献信息

• Increased Enantioselectivity and Remarkable Acceleration of Lipase-Catalyzed Transesterification by Using an Imidazolium PEG–Alkyl Sulfate Ionic Liquid
  作者：Toshiyuki Itoh、Yuichi Matsushita、Yoshikazu Abe、Shi-hui Han、Shohei Wada、Shuichi Hayase、Motoi Kawatsura、Shigeomi Takai、Minoru Morimoto、Yoshihiko Hirose

  DOI：10.1002/chem.200601043

  日期：2006.12.13

  types of imidazolium salt ionic liquids were prepared derived from poly(oxyethylene)alkyl sulfate and used as an additive or coating material for lipase-catalyzed transesterification in an organic solvent. A remarkably increased enantioselectivity was obtained when the salt was added at 3-10 mol % versus substrate in the Burkholderia cepacia lipase (lipase PS-C)-catalyzed transesterification of 1-phenylethanol

  从聚（氧乙烯）烷基硫酸酯制备了几种类型的咪唑鎓盐离子液体，并用作在有机溶剂中脂肪酶催化的酯交换反应的添加剂或涂料。通过在二异丙醚或己烷溶剂体系中使用乙酸乙烯酯，在伯克霍尔德菌洋葱脂肪酶（脂肪酶PS-C）催化的1-苯基乙醇酯交换反应中，以相对于底物3-10 mol％的量添加盐时，可获得显着提高的对映选择性。尤其是，在iPr（2）O溶剂系统中，用脂肪酶PS进行离子液体涂覆可实现显着的加速，同时保持出色的对映选择性。对于某些具有出色对映选择性的底物，它达到了约500至1000倍的加速度。对于IL 1包被的假丝酵母念珠菌脂肪酶也观察到类似的加速。离子液体包被的脂肪酶PS的MALDI-TOF质谱实验表明，离子液体与脂肪酶蛋白结合。
• Remarkable Activation of an Enzyme by (<i>R</i>)-Pyrrolidine- Substituted Imidazolium Alkyl PEG Sulfate
  作者：Yoshikazu Abe、Takuya Hirakawa、Shino Nakajima、Nagisa Okano、Shuichi Hayase、Motoi Kawatsura、Yoshihiko Hirose、Toshiyuki Itoh

  DOI：10.1002/adsc.200800382

  日期：2008.9.5

  The chiral pyrrolidine-substituted imidazolium cetyl-PEG10-sulfate (D-ProMe) derived from D-proline worked as an excellent activating agent of Burkholderia cepacia lipase; it is particularly interesting that the D-isomer of the imidazolium salt worked better than the L-isomer. This suggests that the imidazolium cation group directly interacts with the enzyme protein and causes preferable modification

  衍生自D-脯氨酸的手性吡咯烷取代的咪唑十六烷基-PEG10-硫酸盐（D -ProMe）是伯克霍尔德酒原洋葱脂肪酶的极好活化剂。特别有趣的是，咪唑鎓盐的D-异构体比L-异构体的效果更好。这表明咪唑鎓阳离子基团直接与酶蛋白相互作用并且引起反应性的优选改变。
• A rational design of phosphonium salt type ionic liquids for ionic liquid coated-lipase catalyzed reaction
  作者：Yoshikazu Abe、Kazuhide Yoshiyama、Yusuke Yagi、Shuichi Hayase、Motoi Kawatsura、Toshiyuki Itoh

  DOI：10.1039/c0gc00151a

  日期：——

  A rational design of phosphonium ionic liquid for ionic liquid coated-lipase (IL1-PS)-catalyzed reaction has been investigated, and very rapid transesterification of secondary alcohols accomplished when IL1-PS was used as catalyst in 2-methoxyethoxymethyl(tri-n-butyl)phosphonium bis(trifluoromethanesulfonyl)amide ([P444MEM][NTf2]) as solvent while perfect enantioselectivity was maintaining. Increased Kcat value was suggested to be the most important factor in IL1-PS working the best in [P444MEM][NTf2] solvent.

  一种合理设计的磷阳离子液体用于涂层脂肪酶（IL1-PS）催化反应的研究表明，当使用IL1-PS作为催化剂时，在溶剂2-甲氧基乙氧基甲基（三正丁基）磷阳离子双（三氟甲磺酰）胺（[P444MEM][NTf2]）中，次级醇的酯转移反应非常快速，同时保持了完美的对映选择性。研究表明，Kcat值的增加被认为是IL1-PS在[P444MEM][NTf2]溶剂中表现最佳的最重要因素。
• Inhibitors of IMPDH enzyme
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP1964561A1

  公开（公告）日：2008-09-03

  The present invention relates to compounds which inhibit JMPDH. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting JMPDH enzyme activity and consequently, may be advantageously used as therapeutic agents for IMPDH-mediated processes. This invention also relates to methods for inhibiting the activity of I1VIPDH using the compounds of this invention and related compounds.

  本发明涉及抑制 JMPDH 的化合物。本发明还涉及包含这些化合物的药物组合物。本发明的化合物和药物组合物特别适用于抑制 JMPDH 酶的活性，因此可作为 IMPDH 介导过程的治疗剂。本发明还涉及使用本发明化合物及相关化合物抑制 I1VIPDH 活性的方法。
• Thiacrown Ether Technology in Lipase-Catalyzed Reaction:  Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis
  作者：Toshiyuki Itoh、Koichi Mitsukura、Wipa Kanphai、Yumiko Takagi、Hiroshi Kihara、Hiroshi Tsukube

  DOI：10.1021/jo971288m

  日期：1997.12.1

  Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the-reaction rate of various nitriles was accelerated, the enantioselectivity greatly depended on the nature of the substrate. Among 10 substrates tested, thiacrown ether offered highest enantioselectivity in PCL-catalyzed hydrolysis of 1-(cyanomethyl)propyl acetate. Forty or more times this crown ether, molarity based on the enzyme, was required to attain an acceptably high reaction rate and enantioselectivity. Applying this technology, we succeeded in synthesizing the optically pure attractant pheromone of ant Myrmica scabrinodis (A), (R)-3-octanol and its antipode of (S)-isomer in good overall yields.