3-(furan-2-yl)-2-methyl-3-oxo-butannitrile | 1156898-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(furan-2-yl)-2-methyl-3-oxo-butannitrile
• 英文别名: rac-2-(furan-2-carbonyl)butanenitrile；2-(Furan-2-carbonyl)butanenitrile
• CAS: 1156898-17-7
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: BZWAWPYGIXSKNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(furan-2-yl)-2-methyl-3-oxo-butannitrile 在 potassium 1-hydroxy-1,3-dioxo-1,3-dihydro-1λ(5)-benziodoxol-5-sulfonate 、 甲基三辛基氯化铵 、 sodium chloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以59%的产率得到2-chloro-2-(furan-2-carbonyl)butanenitrile
  参考文献：
  名称：

  氯化钠对活化亚甲基化合物的氧化氯化

  摘要：

  描述了一种用于直接氯化 1,3-二羰基化合物（和相关化合物，如 α-氰基酮）的操作简单的协议。该过程依赖于使用 IBX-SO 3 K 作为化学计量氧化剂和无处不在的氯化钠的温和条件。相转移催化剂的存在有助于在 THF-水混合物中获得良好的产率。

  DOI：

  10.1055/s-0033-1340793
• 作为产物：
  描述：

  2-呋喃甲酰乙腈 、 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77%的产率得到3-(furan-2-yl)-2-methyl-3-oxo-butannitrile
  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

• IBX-Mediated Dehydrogenation of Substituted β-Oxonitriles
  作者：Philipp Klahn、Stefan F. Kirsch

  DOI：10.1002/ejoc.201402007

  日期：2014.5

  convenient method for the mild dehydrogenation of β-oxonitriles is presented. When treated with o-iodoxybenzoic acid (IBX), a range of these compounds were transformed into their unsaturated counterparts. Furthermore, we show that the products of the dehydrogenation can react in situ, undergoing rapid hetero-Diels–Alder reactions with enol ethers to give multiply substituted dihydropyrans. We also describe

  介绍了一种用于 β-氧腈温和脱氢的简便方法。当用邻碘苯甲酸 (IBX) 处理时，这些化合物中的一系列被转化为它们的不饱和对应物。此外，我们表明脱氢产物可以原位反应，与烯醇醚发生快速的杂狄尔斯-阿尔德反应，得到多取代的二氢吡喃。我们还描述了环状 β-氧腈的脱氢，这导致了取代酚的形成。
• 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.
• Oxidative Chlorination of Activated Methylene Compounds with Sodium Chloride
  作者：Stefan Kirsch、Klaus-Daniel Umland、Camilla Mayer

  DOI：10.1055/s-0033-1340793

  日期：——

  An operationally simple protocol for the direct chlorination of 1,3-dicarbonyls (and related compounds such as α-cyano ­ketones) is described. The procedure relies on mild conditions using IBX–SO 3 K as the stoichiometric oxidizing agent and the ubiquitous sodium chloride. The presence of a phase-transfer catalyst is supportive to obtain good yields in a THF–water mixture.

  描述了一种用于直接氯化 1,3-二羰基化合物（和相关化合物，如 α-氰基酮）的操作简单的协议。该过程依赖于使用 IBX-SO 3 K 作为化学计量氧化剂和无处不在的氯化钠的温和条件。相转移催化剂的存在有助于在 THF-水混合物中获得良好的产率。