(+)-3(S)-hydroxy-2-methylenebutanenitrile | 138597-14-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-3(S)-hydroxy-2-methylenebutanenitrile
• 英文别名: (S)-3-hydroxy-2-methylenebutanenitrile；(-)-2-(1-hydroxyethyl)acrylonitrile；(3S)-3-hydroxy-2-methylidenebutanenitrile
• CAS: 138597-14-5
• 化学式: C₅H₇NO
• 分子量: 97.1167
• InChiKey: YWHFEWPKYNNWRC-YFKPBYRVSA-N

物化性质

• 沸点：
  220.9±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)：
  0.1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(1-羟乙基)-丙烯腈 生成 (+)-3(S)-hydroxy-2-methylenebutanenitrile
  参考文献：
  名称：

  Influences of reaction conditions on the enantioselective transesterification using Pseudomonas cepacia lipase

  摘要：

  The influences of different reaction conditions on Pseudomonas cepacia lipase (PCL) catalyzed esterification of several chiral allylic alcohols (2-(1-hydroxy-ethyl)acrylonitrile and some closely related compounds) have been investigated. These compounds are possible precursors in the synthesis of the antibiotic Nyccomycin. An increase in the reaction temperature led to an increased final conversion, decreased enantioselectivity of the reaction, and a reduction of the residual activity of the lipase. PCL is thermostable and catalytically active for more than 100 hours at 100-degrees-C. Variation of the chain length of the acyl group of the esters used as cosubstrates had only a small influence on the conversion. As expected, the alcohol generated during the synthesis had a strong negative influence on the progress of the reaction. PCL showed strong substrate selectivity for some of the tested allylic alcohols. The enantioselectivity changed from substrate to substrate.

  DOI：

  10.1016/s0957-4166(00)86150-9

文献信息

• Substrate Evaluation of<i>Rhodococcus erythropolis</i>SET1, a Nitrile Hydrolysing Bacterium, Demonstrating Dual Activity Strongly Dependent on Nitrile Sub-Structure
  作者：Tracey M. Coady、Lee V. Coffey、Catherine O'Reilly、Claire M. Lennon

  DOI：10.1002/ejoc.201403201

  日期：2015.2

  Rhodococcus erythropolis SET1, a novel nitrile hydrolysing bacterial isolate, has been undertaken with 34 nitriles, 33 chiral and 1 prochiral. These substrates consist primarily of β-hydroxy nitriles with varying alkyl and aryl groups at the β position and containing in several compounds different substituents α to the nitrile. In the case of β-hydroxy nitriles without substitution at the α position

  红球菌 SET1 是一种新型腈水解细菌分离株，已使用 34 种腈、33 种手性和 1 种前手性进行了评估。这些底物主要由 β-羟基腈组成，在 β 位具有不同的烷基和芳基，并且在几种化合物中含有与腈不同的 α 取代基。在 α 位没有取代的 β-羟基腈的情况下，由于分离物的腈水解酶活性，酸是获得的主要产物，以及生物转化后回收的腈。出乎意料的是，当 β-羟基腈在该位置具有乙烯基时，发现酰胺是主要的水解产物。为了进一步探索这种行为，评估了在 α 位置包含吸电子基团的其他相关底物，在 SET1 存在下的生物转化过程中也观察到了酰胺。因此，这种新的分离物也证明了对似乎是底物依赖性的腈类的 NHase 活性。
• Synthesis, lipase catalyzed kinetic resolution, and determination of the absolute configuration of enantiomers of the Morita-Baylis-Hillman adduct 3-hydroxy-2-methylenebutanenitrile
  作者：Daniel J. Strub、Agata Garboś、Stanisław Lochyński

  DOI：10.3998/ark.5550190.p009.749

  日期：——

  3(RS)-Hydroxy-2-methylenebutanenitrile was synthesized from acetaldehyde and acrylonitrile with DABCO as a catalyst. Optimization of the reaction conditions was conducted because some literature procedures were not reproducible. Asymmetric transesterification of the Morita-Baylis-Hillman adduct was carried out using ten lipases. The hydroxyl-nitrile was also esterified chemically and subjected to enzymatic

  以乙醛和丙烯腈为原料，DABCO为催化剂，合成了3(RS)-羟基-2-亚甲基丁腈。对反应条件进行了优化，因为某些文献程序不可重复。Morita-Baylis-Hillman 加合物的不对称酯交换使用十种脂肪酶进行。羟基腈也被化学酯化，并用同一组酶进行酶水解。使用来自南极念珠菌的脂肪酶和 Novozyme 435 获得最佳结果。光学纯羟基腈的绝对构型通过 Mosher 方法确定。
• Influences of reaction conditions on the enantioselective transesterification using Pseudomonas cepacia lipase
  作者：Uwe Bornscheuer、Stefan Schapöhler、Thomas Scheper、Karl Schügerl

  DOI：10.1016/s0957-4166(00)86150-9

  日期：1991.1

  The influences of different reaction conditions on Pseudomonas cepacia lipase (PCL) catalyzed esterification of several chiral allylic alcohols (2-(1-hydroxy-ethyl)acrylonitrile and some closely related compounds) have been investigated. These compounds are possible precursors in the synthesis of the antibiotic Nyccomycin. An increase in the reaction temperature led to an increased final conversion, decreased enantioselectivity of the reaction, and a reduction of the residual activity of the lipase. PCL is thermostable and catalytically active for more than 100 hours at 100-degrees-C. Variation of the chain length of the acyl group of the esters used as cosubstrates had only a small influence on the conversion. As expected, the alcohol generated during the synthesis had a strong negative influence on the progress of the reaction. PCL showed strong substrate selectivity for some of the tested allylic alcohols. The enantioselectivity changed from substrate to substrate.