(S)-3-cyclohexyl-3-hydroxypropanenitrile | 198561-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-cyclohexyl-3-hydroxypropanenitrile
• 英文别名: (S)-3-cyclohexyl-3-hydroxy-propionitrile；(3S)-3-cyclohexyl-3-hydroxypropanenitrile
• CAS: 198561-32-9
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: JTCALPNCEVCXLU-VIFPVBQESA-N

物化性质

• 沸点：
  313.7±15.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  乙酸酐 、 (S)-3-cyclohexyl-3-hydroxypropanenitrile 在 吡啶 作用下， 反应 3.0h， 生成 (S)-2-cyano-1-cyclohexylethyl acetate
  参考文献：
  名称：

  Enantio- and chemoselective bioreduction of β-keto nitriles by the fungus Curvularia lunata

  摘要：

  The use of methanol as cosolvent allows the chemoselective reduction of aromatic beta -keto nitriles by the fungus Curvularia lunata CECT 2130, yielding the corresponding (S)-beta -hydroxy nitriles in a highly enantioselective way. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00348-7
• 作为产物：
  描述：

  2-环己基环氧乙烷 在 Novozym-435 (Candida antarctica Lipase B) 、 氯化铵 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 51.0h， 生成 (S)-3-cyclohexyl-3-hydroxypropanenitrile
  参考文献：
  名称：

  Efficient Lipase-Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β-Hydroxy Nitriles. A Route to Useful Precursors for γ-Amino Alcohols

  摘要：

  DOI：

  10.1002/1615-4169(200108)343:6/7<726::aid-adsc726>3.3.co;2-5

文献信息

• Iridium Diamine Catalyst for the Asymmetric Transfer Hydrogenation of Ketones
  作者：Henar Vázquez-Villa、Stefan Reber、Martin A. Ariger、Erick M. Carreira

  DOI：10.1002/anie.201102732

  日期：2011.9.12

  A simple and very efficient chiral aqua iridium(III) diamine complex leads to excellent enantioselectivities in the asymmetric transfer hydrogenation of various α‐cyano and α‐nitro ketones. The catalyst provides the ortho‐substituted aromatic alcohols with especially high ee values. The diamine ligands can be used directly as chiral ligands; conversion into the corresponding sulfamide is not necessary

  一个简单而高效的手性水合铱（III）二胺络合物可在各种α-氰基和α-硝基酮的不对称转移氢化反应中产生出色的对映选择性。该催化剂可提供具有很高ee值的邻位取代的芳族醇。该二胺配体可直接用作手性配体。不必转化为相应的磺酰胺。
• Cu(I)-Catalyzed Direct Enantioselective Cross Aldol-Type Reaction of Acetonitrile
  作者：Yutaka Suto、Riichiro Tsuji、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1021/ol051423e

  日期：2005.8.1

  Direct catalytic enantioselective cross aldol-type reaction of an acetate surrogate was developed using Cu alkoxide-chiral phosphine complexes as catalysts. Chemoselective activation and deprotonation of the donor substrate (acetonitrile) by the soft metal alkoxide in a strongly donating solvent (HMPA) are key to success in this reaction. Useful chemical yields and promising enantioselectivities are

  使用铜醇盐-手性膦配合物作为催化剂，开发了一种乙酸盐替代物的直接催化对映体选择性十字醇醛型反应。在强供电子溶剂（HMPA）中，软金属醇盐对供体底物（乙腈）的化学选择性活化和去质子化是该反应成功的关键。使用DTBM-SEGPHOS或调谐的BIPHEP作为手性配体可产生有用的化学收率和有希望的对映选择性。[反应：看文字]
• Efficient Lipase-Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β-Hydroxy Nitriles. Correction of Absolute Configuration and Transformation to Chiral β-Hydroxy Acids and γ-Amino Alcohols
  作者：Oscar Pàmies、Jan-E. Bäckvall

  DOI：10.1002/1615-4169(200210)344:9<947::aid-adsc947>3.0.co;2-z

  日期：2002.10

  Chemoenzymatic dynamic kinetic resolution of β-hydroxy nitriles 1 has been carried out using Candida antarctica lipase B and a ruthenium catalyst. The use of a hydrogen source to depress ketone formation in the dynamic kinetic resolution yields the corresponding acetates 2 in good yield and high enantioselectivity. It is shown that the ruthenium catalyst and the enzyme can be recycled when used in

  β-羟基腈1的化学酶动力学动力学拆分已使用南极假丝酵母脂肪酶B和钌催化剂进行。使用氢源以动态动力学拆分抑制酮的形成以良好的产率和高的对映选择性产生相应的乙酸酯2。结果表明，钌催化剂和酶在单独的反应中使用时可以循环使用。我们还报告了从1和2制备各种对映体纯的β-羟基酸衍生物和γ-氨基醇的情况。后一化合物也用于建立1和2的正确绝对构型。
• Engineering a Carbonyl Reductase for Scalable Preparation of ( <i>S</i> )‐3‐Cyclopentyl‐3‐hydroxypropanenitrile, the Key Building Block of Ruxolitinib
  作者：Yunfeng Cui、Liangyan Zhu、Xi Chen、Jinhui Feng、Qiaqing Wu、Dunming Zhu

  DOI：10.1002/cbic.202100589

  日期：2022.3.4

  Rational engineering of the carbonyl reductase PhADH resulted in a double mutant H93C/A139L, which enhanced the enantioselectivity toward the reduction of 3-cyclopentyl-3-ketopropanenitrile 1 a from 85 % to 99 %, as well as a 6-fold improvement in the specific activity. (S)-3-Cyclopentyl-3-hydroxypropanenitrile ((S)-1 b) was prepared at 200 g/L (1.5 M) substrate concentration.

  羰基还原酶 PhADH 的合理工程产生了双突变体 H93C/A139L，这增强了对映选择性将 3-环戊基-3-酮丙腈1a从 85 % 还原到 99 %，并提高了 6 倍具体活动。( S )-3-环戊基-3-羟基丙腈 (( S ) -1b ) 以 200 g/L (1.5 M) 底物浓度制备。
• Biocatalytic strategy toward asymmetric β-hydroxy nitriles and γ-amino alcohols
  作者：Randall W. Nowill、Trisha J. Patel、David L. Beasley、Jose A. Alvarez、Elizah Jackson、Todd J. Hizer、Ion Ghiviriga、Scott C. Mateer、Brent D. Feske

  DOI：10.1016/j.tetlet.2011.03.009

  日期：2011.5

  A library of 20 bakers’ yeast reductases, that are overexpressed in Escherichia coli, were screened against a variety of β-keto nitriles. Enzymes from the aldose reductase and the short chain dehydrogenase family displayed activity toward these substrates. All of the seven substrates were reduced with high enantioselectivities and in some cases both antipodes could be synthesized in high ees. These

  针对各种β-酮腈筛选了在大肠杆菌中过表达的20个面包师酵母还原酶文库。来自醛糖还原酶和短链脱氢酶家族的酶显示出对这些底物的活性。七个底物的全部被高对映体选择性还原，在某些情况下，两种对映体都可以在高ee中合成。这些全细胞反应提供了克量的不对称化合物，这些化合物最终可导致可规模化和简单地合成5-羟色胺再摄取抑制剂和β-肾上腺素阻断剂的新药物类似物。