3-苄氧基-4-氯-丁腈 | 1031428-76-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-苄氧基-4-氯-丁腈
• 英文名称: 3-benzyloxy-4-chloro-butyronitrile
• 英文别名: 3-(benzyloxy)-4-chlorobutanenitrile；4-Chloro-3-phenylmethoxybutanenitrile
• CAS: 1031428-76-8
• 化学式: C₁₁H₁₂ClNO
• 分子量: 209.675
• InChiKey: JLWWWRQNGBALHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-苄氧基-4-氯-丁腈 在 Rhodococcus erythropolis AJ₂₇₀ 作用下， 以 phosphate buffer 为溶剂， 生成 (S)-3-benzyloxy-4-chloro-butyramide 、 (R)-3-benzyloxy-4-chloro-butyramide 、 (S)-4-benzyloxy-dihydrofuran-2(3H)-one 、 (R)-4-benzyloxy-dihydro-2(3H)-furanone
  参考文献：
  名称：

  Nitrile Biotransformations for the Synthesis of Highly Enantioenriched β-Hydroxy and β-Amino Acid and Amide Derivatives: A General and Simple but Powerful and Efficient Benzyl Protection Strategy To Increase Enantioselectivity of the Amidase

  摘要：

  Biotransformations of a number of racemic beta-hydroxy and beta-amino nitrile derivatives were studied using Rhodococcus erythropolis AJ270, the nitrile hydratase and amidase-containing microbial whole cell catalyst, under very mild conditions. The overall enantioselectivity of nitrile biotransformations was governed predominantly by the amidase whose enantioselectivity was switched on remarkably by an O- and a N-benzyl protection group of the Substrates. While biotransformations of beta-hydroxy and beta-amino alkanenitriles gave low yields of amide and acid products of very low enantiomeric purity, introduction of a simple benzyl protection group on the beta-hydroxy and beta-amino of nitrile substrates led to the formation of highly enantioenriched beta-benzyloxy and beta-benzylamino amides and acids in almost quantitative yield. The easy protection and deprotection operations, high chemical yield, and excellent enantioselectivity render the nitrile biotransformation a useful protocol in the synthesis of enantiopure beta-hydroxy and beta-amino acids.

  DOI：

  10.1021/jo800074k
• 作为产物：
  描述：

  在 盐酸 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 作用下， 以 N-甲基吡咯烷酮 、 水 为溶剂， 反应 12.0h， 以65%的产率得到3-苄氧基-4-氯-丁腈
  参考文献：
  名称：

  铜催化自由基开环卤化与 HX

  摘要：

  描述了一种有效的铜催化自由基开环卤化与 HX (aq)。该协议具有氧化还原中性条件、绿色卤素源和广泛的底物范围，为获得中等至良好收率的远端氯化、溴化和碘化烷基酮和烷基腈提供了实用的途径。

  DOI：

  10.1039/d1cc03013b

文献信息

• PROCESS FOR THE PREPARATION OF CHIRAL 3-HYDROXY PYRROLIDINE COMPOUND AND DERIVATIVES THEREOF HAVING HIGH OPTICAL PURITY
  申请人：RStech Corporation

  公开号：EP1926709A1

  公开（公告）日：2008-06-04
• EP1926709A4
  申请人：——

  公开号：EP1926709A4

  公开（公告）日：2009-06-24
• [EN] PROCESS FOR THE PREPARATION OF CHIRAL 3-HYDROXY PYRROLIDINE COMPOUND AND DERIVATIVES THEREOF HAVING HIGH OPTICAL PURITY<br/>[FR] PROCÉDÉ DE SYNTHÈSE D'UN COMPOSÉ CHIRAL DE TYPE 3-HYDROXYPYRROLIDINE ET DE DÉRIVÉS DUDIT COMPOSÉ DE PURETÉ OPTIQUE ÉLEVÉE
  申请人：RSTECH CORP

  公开号：WO2007024113A1

  公开（公告）日：2007-03-01

  [EN] The present invention relates to an effective process for the preparation of optically pure chiral 3-hydroxypyrrolidine or derivatives thereof. More particularly, the present invention relates to an efficient process for the preparation of chiral 3-hydroxypyrrolidine or derivatives thereof, comprised of introducing a suitable protecting group to the starting material 4-chloro-3-hydroxybutyronitrile. Introduction of the hydroxy-protecting group provides advantages: efficient prevention of formation of side products, enhanced performance of the reduction of the nitrile group of the starting material, and enhanced performance of in-situ in¬ tramolecular cyclization. The chiral 3-hydroxypyrrolidine compound is produced in high yield and with high purity.
  [FR] La présente invention concerne un procédé efficace de synthèse de 3-hydroxypyrrolidine chirale optiquement pure ou de dérivés de ce composé. Plus particulièrement, la présente invention concerne un procédé efficace de synthèse de 3-hydroxypyrrolidine chirale ou de dérivés de ce composé, constitué de l'introduction d'un groupement protecteur adapté au niveau du produit de départ, le 4-chloro-3-hydroxybutyronitrile. L'introduction du groupement protecteur de fonction hydroxy confère des avantages : inhibition efficace de la formation de sous-produits, performance améliorée de la réduction du groupement nitrile du produit de départ, et performance améliorée de la cyclisation intramoléculaire in situ. Le composé de type 3-hydroxypyrrolidine chirale est obtenu avec un rendement élevé et une pureté élevée.