(R)-2-hydroxy-2-(4-phenoxyphenyl)acetonitrile | 121986-00-3

• 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: (R)-2-hydroxy-2-(4-phenoxyphenyl)acetonitrile
• 英文别名: (R)-4-Phenoxy-mandelonitrile；(2R)-2-hydroxy-2-(4-phenoxyphenyl)acetonitrile
• CAS: 121986-00-3
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: VDFMGGBUOZRVAV-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-hydroxy-2-(4-phenoxyphenyl)acetonitrile 、 (1R,3R)-3-((Z)-2-氯-3,3,3-三氟-1-丙烯-1-基)-2,2-二甲基环丙烷羧酸 、 N,N'-二环己基碳二亚胺 、 4-二甲氨基吡啶 生成 [(R)-cyano-(4-phenoxyphenyl)methyl] (1R,3R)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
  参考文献：
  名称：

  MATTHEWS, BARRY R.;JACKSON, W. ROY;JAYATILAKE, GAMINI S.;WILSHIRE, COLIN;+, AUSTRAL. J. CHEM., 41,(1988) N1, C. 1697-1709

  摘要：

  DOI：
• 作为产物：
  描述：

  氢氰酸 、 4-苯氧基苯甲醛 在 tartrate buffer 作用下， 以 异丙醚 为溶剂， 反应 216.0h， 以90%的产率得到(R)-2-hydroxy-2-(4-phenoxyphenyl)acetonitrile
  参考文献：
  名称：

  Novel (R)-oxynitrilase sources for the synthesis of (R)-cyanohydrins in diisopropyl ether

  摘要：

  Apple, apricot, cherry and plum meal were prepared from the seeds or kernels of mature garden fruits. The preparations as well as almond meal were used as the source of (R)-oxynitrilase for the synthesis of aliphatic and aromatic cyanohydrins in diisopropyl ether in the presence of 0.1 M tartrate buffer [2% (v/v), pH 5.4]. Apple meal as the most favourable of the enzyme preparations accepts also sterically hindered aldehydes (e.g., pivalaldehyde) as substrates, leading to (R)-cyanohydrins with high enantiopurity (usually ee>90%). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00080-3

文献信息

• (R)- and (S)-cyanohydrins using oxynitrilases in whole cells
  作者：Eero Kiljunen、Liisa T Kanerva

  DOI：10.1016/0957-4166(96)00116-4

  日期：1996.4

  Almond meal and Sorghum bicolor shoots were used as the sources of oxynitrilases for the preparation of a number (R)- and (S)-arylcyanohydrins, respectively, from the corresponding aldehydes in diisopropyl ether. Two different in situ methods were used to introduce hydrogen cyanide into the reaction mixture. In method 1, acetone cyanohydrin decomposes enzymatically and/or chemically to hydrogen cyanide

  杏仁粉和高粱双色芽被用作氧硝化酶的来源，分别从二异丙基醚中的相应醛中制备许多（R）-和（S）-芳基氰醇。使用两种不同的原位方法将氰化氢引入反应混合物中。在方法1中，丙酮氰醇通过酶和/或化学方式分解为氰化氢。在方法2中，氰化氢从二异丙醚中的溶液从反应容器的一个腔室中自由蒸发，最终到达另一个溶解在反应混合物中的区域。
• Asymmetric Addition of Hydrogen Cyanide to Substituted Benzaldehydes Catalyzed by a Synthetic Cyclic Peptide,<i>Cyclo</i>((<i>S</i>)-phenylalanyl-(<i>S</i>)-histidyl)
  作者：Yoshiyuki Kobayashi、Shoichi Asada、Ichigen Watanabe、Hiroaki Hayashi、Yoshiyuki Motoo、Shohei Inoue

  DOI：10.1246/bcsj.59.893

  日期：1986.3

  Using cyclo((S)-phenylalanyl-(S)-histidyl) as catalyst, optically active cyanohydrins from substituted benzaldehydes with p-methyl, m-methyl, o-methyl, m-methoxyl, or m-phenoxyl group were obtained with optical yield of 82–33%. For the asymmetric cyanohydrin synthesis, nonpolar solvent such as benzene or carbon tetrachloride was advantageous, while no asymmetric synthesis took place in methanol or

  以环((S)-苯丙氨酰-(S)-组氨酸)为催化剂，由对甲基、间甲基、邻甲基、间甲氧基或间苯氧基取代的苯甲醛通过旋光反应获得旋光性氰醇。产率为 82-33%。对于不对称氰醇合成，苯或四氯化碳等非极性溶剂是有利的，而在甲醇或二甲亚砜中不发生不对称合成。
• BINOLAM, a Recoverable Chiral Ligand for Bifunctional Enantioselective Catalysis:  The Asymmetric Synthesis of Cyanohydrins
  作者：Jesús Casas、Carmen Nájera、José M. Sansano、José M. Saá

  DOI：10.1021/ol0262338

  日期：2002.7.1

  [reaction: see text] A new bifunctional catalytic system based on a monometallic aluminum complex is used for the efficient enantioselective cyanation of aldehydes. The ligand (S)- or (R)-2,2'-bis(diethylaminomethyl)-substituted binaphthol (BINOLAM) used is recovered for recycling. This methodology is used for the synthesis of a precursor of epothilone A.

  [反应：见正文]基于单金属铝络合物的新型双功能催化系统用于醛的有效对映选择性氰化。回收所使用的配体（S）-或（R）-2,2'-双（二乙基氨基甲基）-取代的联萘酚（BINOLAM）以循环使用。该方法用于合成埃博霉素A的前体。
• Matthews, Barry R.; Jackson, W. Roy; Jayatilake, Gamini S., Australian Journal of Chemistry, 1988, vol. 41, # 11, p. 1697 - 1710
  作者：Matthews, Barry R.、Jackson, W. Roy、Jayatilake, Gamini S.、Wilshire, Colin、Jacobs, Howard A.

  DOI：——

  日期：——