(S)-4-(oxiran-2-yl)benzonitrile | 179694-33-8

• 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)-4-(oxiran-2-yl)benzonitrile
• 英文别名: (S)-p-Cyanostyrene oxide；4-[(2S)-oxiran-2-yl]benzonitrile
• CAS: 179694-33-8
• 化学式: C₉H₇NO
• 分子量: 145.161
• InChiKey: WLNIRLBZLAAEAQ-SECBINFHSA-N

物化性质

• 熔点：
  58-60 °C
• 沸点：
  285.7±28.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-4-(oxiran-2-yl)benzonitrile 在 wild-type epoxide hydrolase (Agrobacterium radiobacter AD₁) tris-buffer 、 水 作用下， 以 二甲基亚砜 为溶剂， 生成 (S)-1-(4-cyanophenyl)-1,2-ethanediol
  参考文献：
  名称：

  Biocatalytic Potential of the Epoxide Hydrolase from Agrobacterium radiobacter AD1 and a Mutant with Enhanced Enantioselectivity

  摘要：

  Optically pure epoxides are useful synthons for a variety of biologically active compounds. The epoxide hydrolase obtained from Agrobacterium radiobacter AD1 hydrolyses racemic aryl epoxides with moderate and aliphatic epoxides with low enantioselectivity. The three-dimensional structure of this enzyme indicates that two tyrosine residues interact with the epoxide oxygen. Mutating one of these, tyrosine 215, to a phenylalanine (Y215F) resulted in an enzyme with increased enantioselectivity towards aryl epoxides. The relatively strong decrease in activity towards the remaining enantiomers makes this enzyme a much better biocatalyst than the wild-type enzyme for the preparation of optically pure (S)-styrene oxide derivatives.

  DOI：

  10.1002/1615-4169(200210)344:9<980::aid-adsc980>3.0.co;2-a
• 作为产物：
  描述：

  2-溴-4'-氰基苯乙酮 在 (S)-3,3-diphenyltetrahydro-3H-1l4-spiro[pyrrolo[1,2-c][1,3,2]oxazaborole-1,2'-[1,3,2]dioxaborolane] 、 dimethyl sulfide borane 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 生成 (S)-4-(oxiran-2-yl)benzonitrile
  参考文献：
  名称：

  螺硼酸酯催化硼烷还原 2-卤代酮制备手性环氧化物：在光学纯 1,2-羟基醚和 1,2-叠氮醇合成中的应用

  摘要：

  描述了以 10% 螺氨基硼酸酯1作为催化剂，对映选择性硼烷介导的多种 2-卤代酮的还原反应。通过 2-卤代醇的简单基础处理，可以高产率和优异的对映体纯度（高达 99% ee）获得光学活性环氧化物。在不同的反应条件下研究了环氧乙烷与酚盐或叠氮化钠的开环，得到具有优异对映选择性 (99% ee) 和良好至高化学收率的非外消旋 1,2-羟基醚和 1,2-叠氮醇。

  DOI：

  10.1021/jo102294j

文献信息

• Engineered P450pyr monooxygenase for asymmetric epoxidation of alkenes with unique and high enantioselectivity
  作者：Aitao Li、Ji Liu、Son Q. Pham、Zhi Li

  DOI：10.1039/c3cc46675b

  日期：——

  A triple mutant of P450pyr monooxygenase (P450pyrTM) catalysed the epoxidation of several para-substituted styrenes as the first enzyme showing high (R)-enantioselectivity and high conversion, demonstrated a broad substrate range, and showed high enantioselectivity for the epoxidation of an unconjugated 1,1-disubstituted alkene, 2-methyl-3-phenyl-1-propene, and a cyclic alkene, N-phenoxycarbonyl-1,2,5,6-tetrahydropyridine, respectively.

  P450pyr单加氧酶的三重突变体（P450pyrTM）作为首个展现出高（R）对映选择性和高转化率的酶，催化了几种对位取代苯乙烯的环氧化反应，其底物范围广泛，并对非共轭的1,1-二取代烯烃——2-甲基-3-苯基-1-丙烯，以及环烯烃——N-苯氧羰基-1,2,5,6-四氢吡啶的环氧化反应表现出高对映选择性。
• [EN] SPHINGOSINE-1-PHOSPHATE RECEPTOR AGONISTS<br/>[FR] AGONISTES DES RÉCEPTEURS SPHINGOSINE-1-PHOSPHATE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011017578A1

  公开（公告）日：2011-02-10

  Disclosed are compounds of Formula (I), or a stereoisomer or a pharmaceutically acceptable salt thereof, wherein: A is formula (II) Q is a substituted 5-membered monocyclic heteroaryl group; W is CH2, O, or NH; and R1, R2, R3, R4, R5, R6, m, n, t, and x are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

  揭示了Formula (I)的化合物，或其立体异构体或药用可接受的盐，其中：A为Formula (II)，Q为取代的5-成员单环杂芳基团；W为CH2、O或NH；而R1、R2、R3、R4、R5、R6、m、n、t和x在此处有定义。还揭示了将这些化合物用作G蛋白偶联受体S1P1的选择性激动剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗、预防或减缓多种治疗领域的疾病或紊乱方面具有用处，如自身免疫疾病和血管疾病。
• Microbiological Transformations. 33. Fungal Epoxide Hydrolases Applied to the Synthesis of Enantiopure <i>Para</i>-Substituted Styrene Oxides. A Mechanistic Approach
  作者：S. Pedragosa-Moreau、C. Morisseau、J. Zylber、A. Archelas、J. Baratti、R. Furstoss

  DOI：10.1021/jo960558i

  日期：1996.1.1

  para-substituted styrene oxide derivatives was studied, using whole cells of the fungi Aspergillus niger or Beauveria sulfurescens. These microorganisms proved to be equipped with epoxide hydrolases which are able to achieve these hydrolyses with high enantioselectivity. This allowed the preparation of the optically active epoxides and of the corresponding vicinal diols which were obtained with good to excellent

  使用黑曲霉或白僵菌的全细胞研究了不同对位取代的氧化苯乙烯衍生物的生物水解。这些微生物被证明配备有环氧化物水解酶，其能够以高对映选择性实现这些水解。这样就可以制备旋光性环氧化物和相应的邻位二醇，它们的对映体纯度很好。这两种微生物被证明是对映体互补的。使用来自黑曲霉的粗冻干酶提取物进行的机理研究通过哈米特系数图表明该水解很可能是由于一般的碱催化过程。
• The Stereoselective Oxidation of <i>para</i> ‐Substituted Benzenes by a Cytochrome P450 Biocatalyst
  作者：Rebecca R. Chao、Ian C.‐K. Lau、Tom Coleman、Luke R. Churchman、Stella A. Child、Joel H. Z. Lee、John B. Bruning、James J. De Voss、Stephen G. Bell

  DOI：10.1002/chem.202102757

  日期：2021.10.21

  The efficient and sustainable hydroxylation, epoxidation and sulfoxidation of a wide range of benzene derivatives using an engineered variant of a bacterial cytochrome P450 enzyme is reported. These reactions were catalyzed with high activity, regioselectivity and total turnover number (up to 20,000) and in certain instances these reactions were achieved with high enanatioselectivity (up to 98 % ee

  报道了使用细菌细胞色素 P450 酶的工程变体对各种苯衍生物进行有效和可持续的羟基化、环氧化和磺化氧化。这些反应以高活性、区域选择性和总转换数（高达 20,000）催化，在某些情况下，这些反应以高对映选择性（高达 98% ee .）实现。
• Asymmetric epoxidation of alkenes and benzylic hydroxylation with P450tol monooxygenase from Rhodococcus coprophilus TC-2
  作者：Aitao Li、Shuke Wu、Joseph P. Adams、Radka Snajdrova、Zhi Li

  DOI：10.1039/c4cc03491k

  日期：——

  P450tol monooxygenase was discovered as a unique and highly enantioselective enzyme for asymmetric epoxidation of some terminal alkenes containing electron-withdrawing groups and benzylic hydroxylation of several ethylbenzenes giving the corresponding useful and valuable products, such as (R)-2- and 3-substituted styrene oxides, (S)-4-substituted styrene oxides, and (S)-benzylic alcohols, in high ee

  发现P450tol单加氧酶是一种独特的高对映选择性酶，用于某些含吸电子基团的末端烯烃的不对称环氧化和若干乙苯的苄基羟基化作用，从而提供相应的有用和有价值的产物，例如（R）-2-和3-取代的苯乙烯高ee的三价氧化物，（S）-4-取代的苯乙烯氧化物和（S）-苄基醇。