2-(2-bromophenyl)-2-hydroxyacetonitrile | 570361-05-6

• 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: 2-(2-bromophenyl)-2-hydroxyacetonitrile
• 英文别名: 2-Bromobenzaldehyde cyanohydrin；(2S)-2-(2-bromophenyl)-2-hydroxyacetonitrile
• CAS: 570361-05-6
• 化学式: C₈H₆BrNO
• 分子量: 212.046
• InChiKey: BJJDHOPCQJHYQH-MRVPVSSYSA-N

物化性质

• 沸点：
  347.3±27.0 °C(Predicted)
• 密度：
  1.630±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：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2-(2-bromophenyl)-2-hydroxyacetonitrile 在 盐酸 、 水 作用下， 反应 2.0h， 生成 (S)-2-bromo-mandelic acid
  参考文献：
  名称：

  Solid Phase Behavior in the Chiral Systems of Various 2-Hydroxy-2-phenylacetic Acid (Mandelic Acid) Derivatives

  摘要：

  The solid phase behavior of a series of monosubstituted F-, Cl-, Br-, I-, and CH3- and two 2,4-halogen-disubstituted 2-hydroxy-2-phenylacetic acid (mandelic acid) derivatives was investigated. The study includes detailed information about melting temperature, melting enthalpy, Xray diffraction data, as well as selected binary phase diagrams of the respective chiral systems. Aside from the known metastable metastable conglomerates was found.

  DOI：

  10.1021/je500845d
• 作为产物：
  描述：

  氢氰酸 、 邻溴苯甲醛 在 hydroxynitrile lyase from Manihot esculenta immobilized on Sylgard 184 作用下， 以 异丙醚 为溶剂， 生成 2-(2-bromophenyl)-2-hydroxyacetonitrile
  参考文献：
  名称：

  Solid Phase Behavior in the Chiral Systems of Various 2-Hydroxy-2-phenylacetic Acid (Mandelic Acid) Derivatives

  摘要：

  The solid phase behavior of a series of monosubstituted F-, Cl-, Br-, I-, and CH3- and two 2,4-halogen-disubstituted 2-hydroxy-2-phenylacetic acid (mandelic acid) derivatives was investigated. The study includes detailed information about melting temperature, melting enthalpy, Xray diffraction data, as well as selected binary phase diagrams of the respective chiral systems. Aside from the known metastable metastable conglomerates was found.

  DOI：

  10.1021/je500845d

文献信息

• Enantioselective cyanosilylation of aldehydes catalyzed by novel camphor derived Schiff bases-titanium(IV) complexes
  作者：Ewelina Błocka、Mariusz J. Bosiak、Mirosław Wełniak、Agnieszka Ludwiczak、Andrzej Wojtczak

  DOI：10.1016/j.tetasy.2014.03.001

  日期：2014.4

  Five tridentate Schiff bases have been prepared from (1R,2S,3R,4S)-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol and salicylaldehydes. X-ray structure investigation revealed differences in their molecular conformation, and their titanium(IV) complexes have been studied with NMR techniques. Among them the complex with the Schiff base obtained from 2-hydroxy-3-isopropylbenzaldehyde, is the most selective

  五三齿席夫碱已经从（1制备- [R，2小号，3 - [R，4小号）-3-氨基- 1,7,7-三甲基二环[2.2.1]庚-2-醇和水杨醛。X射线结构的调查显示在它们的分子构象的差异，和它们的钛（IV）络合物进行了研究NMR技术。它们之间的复合物与由2-羟基-3-异丙基苯甲醛得到的席夫碱，为脂肪族，脂环族，芳族，杂芳族和醛的硅氰化反应最有选择性的催化剂。最高的对映选择性，> 99％时，在加入三甲基氰硅烷的给肉桂醛实现。
• Enantioselective cyanosilylation of aldehydes catalyzed by a multistereogenic salen–Mn(<scp>iii</scp>) complex with a rotatable benzylic group as a helping hand
  作者：Yun-Long Wei、Wei-Sheng Huang、Yu-Ming Cui、Ke-Fang Yang、Zheng Xu、Li-Wen Xu

  DOI：10.1039/c4ra12884b

  日期：——

  A multistereogenic salen–Mn(iii) complex bearing an aromatic pocket and two benzylic groups as helping hands was found to be efficient in the catalysis of asymmetric cyanosilylation.

  一种具有芳香口袋和两个苄基辅助作用的多手性salen-Mn（III）配合物被发现在不对称氰基硅化反应中具有高效催化作用。
• Enzymatic kinetic resolution of racemic cyanohydrins via enantioselective acylation
  作者：Qing Xu、Yongli Xie、Xiaohong Geng、Peiran Chen

  DOI：10.1016/j.tet.2009.11.074

  日期：2010.1

  Enzymatic kinetic resolution of a series of aromatic and aliphatic cyanohydrins in organic media has been investigated. The behavior of potential lipases, molecular sieves, acyl reagent, reaction temperature, and organic solvents on the kinetic resolution was studied. The influence of substrate structure, steric, and electronic nature and position of the aryl substituent on the enantioselectivity was

  已经研究了有机介质中一系列芳香族和脂肪族氰醇的酶促动力学拆分。研究了潜在的脂肪酶，分子筛，酰基试剂，反应温度和有机溶剂对动力学拆分的影响。讨论了底物结构，空间和电子性质以及芳基取代基的位置对对映选择性的影响。在优化的反应条件下，大多数研究的化合物均可实现良好的对映选择性。具体地，可以以大于200的动力学对映体比率（E）来分解基板1a，1c，1d，1f，1u。
• Chiral linear polymers bonded alternatively with salen and 1,4-dialkoxybenzene: synthesis and application for Ti-catalyzed asymmetric TMSCN addition to aldehydes
  作者：Sekarpandi Sakthivel、Tharmalingam Punniyamurthy

  DOI：10.1016/j.tetasy.2010.11.020

  日期：2010.12

  the asymmetric addition of TMSCN to aldehydes while the selectivity of the polymer catalyst is identical to that of the monomer. The reactions are efficient affording the cyanohydrins with up to 88% ee. The selectivity of the polymer based catalyst 9a is found to be the same to that of the monomer 10a. The reaction provides the advantages of simplified product isolation and easy recovery and recyclability

  已经完成了以salen和1,4-二辛氧基苯为交替链段的手性线性聚合物1a – b的合成。GPC分析显示出对应于约3的分子量。15个（M w  = 10,999，M n  = 9165和PDI = 1.20）1a和ca的重复单元。 对于1b重复8（M w  = 8547，M n = 7883和PDI = 1.08）重复单元。用Ti（O i Pr）4研究了聚合物1a – b作为可再循环的催化剂，用于将TMSCN不对称加成到醛中，而聚合物催化剂的选择性与单体的选择性相同。该反应有效地提供了高达88％ee的氰醇。发现基于聚合物的催化剂9a的选择性与单体10a的选择性相同。该反应的优点是简化了产物分离，并且聚合物催化剂9a易于回收和再循环，而没有任何活性或选择性的损失。
• [EN] SEQUENCES ENCODING S-HYDROXYNITRIL LYASES AND THEIR USE IN METHODS FOR THE PRODUCTION OF CYANOHYDRINS<br/>[FR] SEQUENCES CODANT DES S-HYDROXYNITRILE LYASES ET UTILISATION DE CELLES-CI DANS DES PROCEDES DE PRODUCTION DE CYANOHYDRINES
  申请人：BASF AG

  公开号：WO2004090124A2

  公开（公告）日：2004-10-21

  The present invention relates to new aminoacid sequences isolated from Adenia racemosa encoding S-hydroxynitrile lyases and their use in methods for the production of nitriles and/or carboxylic acids, preferably optically active nitriles and/or carboxylic acids. The invention further relates to nucleic acid encoding said S-hydroxynitrile lyases, recombinant expression constructs comprising said nucleic acid sequences, recombinant vectors comprising the nucleic acid sequences or the expression constructs, to recombinant organisms, preferably microorganisms or yeasts, comprising the nucleic acid sequences, expression constructs or vectors. The invention additionally relates to a method for the production of cyanohydrins and/or carboxylic acids, preferably optically active cyanohydrins and/or carboxylic acids from racemic aldehydes and cyanide.