rac-2-(thiophene-2-carbonyl)butanenitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-2-(thiophene-2-carbonyl)butanenitrile
• 英文别名: 2-(Thiophene-2-carbonyl)butanenitrile
• 化学式: C₉H₉NOS
• 分子量: 179.243
• InChiKey: RAURFQPBOKXBPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-噻吩基乙酰腈	2-Thenoylacetonitrile	33898-90-7	C7H5NOS	151.189

反应信息

• 作为反应物：
  描述：

  rac-2-(thiophene-2-carbonyl)butanenitrile 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 rac-2-(hydroxy(thiophen-2-yl)methyl)butanenitrile
  参考文献：
  名称：

  Efficient methodology to produce a duloxetine precursor using whole cells of Rhodotorula rubra

  摘要：

  Different types of yeasts were employed as biocatalysts in the reduction of beta-ketonitriles. The red microorganism, Rhodotorula rubra, was selected as the best performing catalyst in the reduction of different substituted ketonitriles giving total stereoselectivity in most cases (90-99% ee). In particular, its use as fresh and lyophilised cells was expanded to a semi-preparative scale for the production of the duloxetine precursor 1a, R. rubra was screened in the reduction of alkylation products in comparison with Pichia henricii for assignment of configuration of products 2a and 11a after derivatisation with S-MPA. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2016.04.002
• 作为产物：
  描述：

  2-噻吩基乙酰腈 、 葡萄糖 在 Saccharomyces cerevisiae Zeus whole cell 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 为溶剂， 以88%的产率得到rac-2-(thiophene-2-carbonyl)butanenitrile
  参考文献：
  名称：

  Efficient methodology to produce a duloxetine precursor using whole cells of Rhodotorula rubra

  摘要：

  Different types of yeasts were employed as biocatalysts in the reduction of beta-ketonitriles. The red microorganism, Rhodotorula rubra, was selected as the best performing catalyst in the reduction of different substituted ketonitriles giving total stereoselectivity in most cases (90-99% ee). In particular, its use as fresh and lyophilised cells was expanded to a semi-preparative scale for the production of the duloxetine precursor 1a, R. rubra was screened in the reduction of alkylation products in comparison with Pichia henricii for assignment of configuration of products 2a and 11a after derivatisation with S-MPA. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2016.04.002

文献信息

• Efficient methodology to produce a duloxetine precursor using whole cells of Rhodotorula rubra
  作者：Isabella Rimoldi、Giorgio Facchetti、Donatella Nava、Martina Letizia Contente、Raffella Gandolfi

  DOI：10.1016/j.tetasy.2016.04.002

  日期：2016.6

  Different types of yeasts were employed as biocatalysts in the reduction of beta-ketonitriles. The red microorganism, Rhodotorula rubra, was selected as the best performing catalyst in the reduction of different substituted ketonitriles giving total stereoselectivity in most cases (90-99% ee). In particular, its use as fresh and lyophilised cells was expanded to a semi-preparative scale for the production of the duloxetine precursor 1a, R. rubra was screened in the reduction of alkylation products in comparison with Pichia henricii for assignment of configuration of products 2a and 11a after derivatisation with S-MPA. (C) 2016 Published by Elsevier Ltd.