(S)-2-(1-hydroxyethyl)benzonitrile | 1363508-16-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-(1-hydroxyethyl)benzonitrile
• 英文别名: 1-2’-(cyanophenyl)ethanol；2-[(1S)-1-Hydroxyethyl]benzonitrile；2-[(1S)-1-hydroxyethyl]benzonitrile
• CAS: 1363508-16-0
• 化学式: C₉H₉NO
• 分子量: 147.177
• InChiKey: QUUYOBOUUVMQCH-ZETCQYMHSA-N

物化性质

• 沸点：
  300.7±25.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(1-hydroxyethyl)benzonitrile 在 盐酸 、 水 作用下， 反应 48.0h， 以99%的产率得到(3S)-3-甲基-2-苯并呋喃-1(3H)-酮
  参考文献：
  名称：

  Highly Stereoselective Chemoenzymatic Synthesis of the 3H-Isobenzofuran Skeleton. Access to Enantiopure 3-Methylphthalides

  摘要：

  A straightforward synthesis of (S)-3-methylphthalides has been developed, with the key asymmetric step being the bioreduction of 2-acetylbenzonitriles. Enzymatic processes have been found to be highly dependent on the pH value, with acidic conditions being required to avoid undesired side reactions. Baker's yeast was found lobe the best biocatalyst acting in a highly stereoselective fashion. The simple treatment of the reaction crudes with aqueous HCl has provided access to enantiopure (S)-3-methylphthalides in moderate to excellent yields.

  DOI：

  10.1021/ol300191s
• 作为产物：
  描述：

  2-乙酰苯甲腈 在 glucose dehydrogenase 、 葡萄糖 、 ketoreductase from Pichia glucozyma 、 nicotinamide adenine dinucleotide phosphate 作用下， 以 aq. buffer 为溶剂， 以98%的产率得到(S)-2-(1-hydroxyethyl)benzonitrile
  参考文献：
  名称：

  用葡萄糖氧化毕赤酵母的苯甲酰还原酶（KRED1-Pglu）对苯乙酮衍生物进行酶促还原：对活性和对映体选择性的电子和空间影响†

  摘要：

  来自葡糖毕赤酵母的重组酮还原酶（KRED1-Pglu）被用于对映选择性还原各种单取代的苯乙酮。的反应速率元-和对位-衍生物是与所描述的电子效果一致σ -Hammett系数; 另一方面，对映选择性由结合口袋中底物的相反方向决定。仅在带有低空间影响的取代基（即F和CN）的底物上发生邻位衍生物的还原。反应性受立体电子特征控制（CO长度和电荷，LUMO前沿分子轨道的形状），可以从理论上计算出来。

  DOI：

  10.1039/c6ob00047a

文献信息

• Enantioselective Hydroboration of Ketones Catalyzed by Rare-Earth Metal Complexes Containing Trost Ligands
  作者：Yuli Sun、Chengrong Lu、Bei Zhao、Mingqiang Xue

  DOI：10.1021/acs.joc.0c00877

  日期：2020.8.21

  dinuclear rare-earth metal complexes [REL1]2 (RE = Y(1), Eu(2), Nd(3), La (4)) stabilized by Trost proligand H3L1 (H3L1 = (S,S)-2,6-bis[2-(hydroxydiphenylmethyl)pyrrolidin-1-ylmethyl]-4-methylphenol) were first prepared, and all were characterized by X-ray diffraction. Complex 4 was employed as the catalyst for enantioselective hydroboration reaction of substituted ketones, and the corresponding secondary

  四个手性双核稀土金属络合物[REL 1 ] 2（RE = Y（1），Eu（2），Nd（3），La（4））由Trost proligand H 3 L 1（H 3 L 1 =首先制备（S，S）-2，6-双[2-（羟基二苯基甲基）吡咯烷-1-基甲基] -4-甲基苯酚，并通过X射线衍射对其进行表征。复杂4将其用作取代酮的对映选择性硼氢化反应的催化剂，使用还原剂HBpin可制得具有优异收率和较高ee值的相应仲醇。同样的结果，使用镧酰胺的La [N（森的组合也实现3）2 ] 3与特罗斯特前配体ħ 3大号1 1的摩尔比：在一个1。实验结果和DFT计算揭示了对映选择性硼氢化反应的可能机理，并确定了当前系统中对映选择性的起源。
• Enzymatic reduction of acetophenone derivatives with a benzil reductase from Pichia glucozyma (KRED1-Pglu): electronic and steric effects on activity and enantioselectivity
  作者：Martina L. Contente、Immacolata Serra、Luca Palazzolo、Chiara Parravicini、Elisabetta Gianazza、Ivano Eberini、Andrea Pinto、Benedetta Guidi、Francesco Molinari、Diego Romano

  DOI：10.1039/c6ob00047a

  日期：——

  (KRED1-Pglu) was used for the enantioselective reduction of various mono-substituted acetophenones. Reaction rates of meta- and para-derivatives were consistent with the electronic effects described by σ-Hammett coefficients; on the other hand, enantioselectivity was determined by an opposite orientation of the substrate in the binding pocket. Reduction of ortho-derivatives occurred only with substrates

  来自葡糖毕赤酵母的重组酮还原酶（KRED1-Pglu）被用于对映选择性还原各种单取代的苯乙酮。的反应速率元-和对位-衍生物是与所描述的电子效果一致σ -Hammett系数; 另一方面，对映选择性由结合口袋中底物的相反方向决定。仅在带有低空间影响的取代基（即F和CN）的底物上发生邻位衍生物的还原。反应性受立体电子特征控制（CO长度和电荷，LUMO前沿分子轨道的形状），可以从理论上计算出来。
• Highly Stereoselective Chemoenzymatic Synthesis of the 3<i>H</i>-Isobenzofuran Skeleton. Access to Enantiopure 3-Methylphthalides
  作者：Juan Mangas-Sánchez、Eduardo Busto、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1021/ol300191s

  日期：2012.3.16

  A straightforward synthesis of (S)-3-methylphthalides has been developed, with the key asymmetric step being the bioreduction of 2-acetylbenzonitriles. Enzymatic processes have been found to be highly dependent on the pH value, with acidic conditions being required to avoid undesired side reactions. Baker's yeast was found lobe the best biocatalyst acting in a highly stereoselective fashion. The simple treatment of the reaction crudes with aqueous HCl has provided access to enantiopure (S)-3-methylphthalides in moderate to excellent yields.