3-O-(benzoyl)-glutaronitrile | 138145-58-1

• 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: 3-O-(benzoyl)-glutaronitrile
• 英文别名: 3-benzoyloxypentanedinitrile；3-Benzoyloxyglutaronitrile；1,3-dicyanopropan-2-yl benzoate
• CAS: 138145-58-1
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: ALRNVXTYQVFJLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-O-(benzoyl)-glutaronitrile 在 氯化亚砜 作用下， 反应 6.0h， 生成 Benzoic acid (S)-2-cyano-1-[((R)-1-naphthalen-1-yl-ethylcarbamoyl)-methyl]-ethyl ester
  参考文献：
  名称：

  3-取代戊二腈的微生物水解

  摘要：

  Rhodococcus butanica ATCC 21197 优先水解带有芳香环的 3-取代戊二腈的 pro-S 氰基。3-苯甲酰氧基衍生物得到高ee(>99%)的产物。

  DOI：

  10.1246/cl.1991.1823
• 作为产物：
  描述：

  3-羟基戊二腈 、 苯甲酰氯 在 吡啶 作用下， 反应 2.0h， 以96%的产率得到3-O-(benzoyl)-glutaronitrile
  参考文献：
  名称：

  Stereoselective hydrolysis of nitriles and amides under mild conditions using a whole cell catalyst

  摘要：

  An immobilised whole cell Rhodococcus sp. (SP 361) has been shown to be an effective catalyst for the stereoselective hydrolysis of both racemic and prochiral nitrile containing compounds. 2-Alkyl-arylacetonitriles 6a-8a were hydrolysed to (S)-acids and (R)-amides whereas the closely related substrate 9a gave the (R)-acid. A series of prochiral dinitriles 10a-13a were hydrolysed to the corresponding (S)-acids with e.e.'s 22-84%. Models to account for the stereoselectivity of the enzymic hydrolyses have been proposed.

  DOI：

  10.1016/s0957-4166(00)80215-3

文献信息

• Enzymic hydrolysis of prochiral dinitriles
  作者：John A. Crosby、Julian S. Parratt、Nicholas J. Turner

  DOI：10.1016/s0957-4166(00)86057-7

  日期：1992.12

  A series of prochiral 3-hydroxyglutaronitrile derivatives 1–5 has been enzymically hydrolysed to the corresponding nitrile-carboxylic acids 1b–5b with enantiomeric excesses ranging from 22–84%. In all cases the products were of the (S)-configuration.

  一系列手性3-羟基戊二腈衍生物1-5已被酶解为相应的腈羧酸1b-5b，对映体过量范围为22-84％。在所有情况下，产品均为（S）-构型。
• A Stereodivergent Approach to Substituted 4-Hydroxypiperidines
  作者：Mandy K. S. Vink、Christien A. Schortinghuis、Jordy Luten、Jan H. van Maarseveen、Hans E. Schoemaker、Henk Hiemstra、Floris P. J. T. Rutjes

  DOI：10.1021/jo025943o

  日期：2002.11.1

  A stereodivergent route toward both diastereomeric forms of functionalized 4-hydroxypiperidines has been successfully developed. This route involves biocatalytic generation of the enantiopure starting materials followed by functionalization via N-acyliminium ion-mediated CC-bond formation.
• Crosby John A., Parratt Julian S., Turner Nicholas J., Tetrahedron, 3 (1992) N 12, S 1547-1550
  作者：Crosby John A., Parratt Julian S., Turner Nicholas J.

  DOI：——

  日期：——
• Stereoselective hydrolysis of nitriles and amides under mild conditions using a whole cell catalyst
  作者：Timothy Beard、Mark A. Cohen、Julian S. Parratt、Nicholas J. Turner、John Crosby、Jock Moilliet

  DOI：10.1016/s0957-4166(00)80215-3

  日期：1993.6

  An immobilised whole cell Rhodococcus sp. (SP 361) has been shown to be an effective catalyst for the stereoselective hydrolysis of both racemic and prochiral nitrile containing compounds. 2-Alkyl-arylacetonitriles 6a-8a were hydrolysed to (S)-acids and (R)-amides whereas the closely related substrate 9a gave the (R)-acid. A series of prochiral dinitriles 10a-13a were hydrolysed to the corresponding (S)-acids with e.e.'s 22-84%. Models to account for the stereoselectivity of the enzymic hydrolyses have been proposed.
• Microbial Hydrolysis of 3-Substituted Glutaronitriles
  作者：Hideaki Kakeya、Naoko Sakai、Akio Sano、Masahiro Yokoyama、Takeshi Sugai、Hiromichi Ohta

  DOI：10.1246/cl.1991.1823

  日期：1991.10

  Rhodococcus butanica ATCC 21197 preferentially hydrolyzed pro-S cyano group of 3-substituted glutaronitriles with an aromatic ring. A product with high e.e. (>99%) was obtained from 3-benzoyloxy derivative.

  Rhodococcus butanica ATCC 21197 优先水解带有芳香环的 3-取代戊二腈的 pro-S 氰基。3-苯甲酰氧基衍生物得到高ee(>99%)的产物。