1-methyl-3-oxocyclopentane-1-carbonitrile | 112496-87-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-3-oxocyclopentane-1-carbonitrile
• 英文别名: 1-Methyl-3-oxocyclopentanecarbonitrile
• CAS: 112496-87-4
• 化学式: C₇H₉NO
• 分子量: 123.155
• InChiKey: OOGKBJYFGKSSNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲基-2-环戊烯-1-酮 在 三乙基铝 、 四氯化钛 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-methyl-3-oxocyclopentane-1-carbonitrile
  参考文献：
  名称：

  （dl）-沙克霉素和相关化合物的腈和甲酯的合成

  摘要：

  腈和酯对应于（DL）-sarkomycin，6-和7-元环类似物腈，和3-甲基取代的腈制备。将氰基三甲基硅烷共轭添加到环状α-烯酮中，得到3-三甲基甲硅烷氧基2-环烯烃腈。它们用氯甲基苯硫醚进行烷基化，然后将酮氧化成砜，然后在碱性氧化铝上消除亚磺酸，生成α-亚甲基羰基化合物。获得该酯涉及3-氧代2-苯基硫代甲基环戊烷腈的缩醛化，碱性水解成酸，脱缩醛化，酯化，氧化和消除亚磺酸。

  DOI：

  10.1016/s0040-4020(01)89959-2

文献信息

• Deboronative cyanation of potassium alkyltrifluoroborates via photoredox catalysis
  作者：Jian-Jun Dai、Wen-Man Zhang、Yong-Jin Shu、Yu-Yang Sun、Jun Xu、Yi-Si Feng、Hua-Jian Xu

  DOI：10.1039/c6cc01530a

  日期：——

  The radical deboronative cyanation of alkyltrifluoroborates with a broad range of functional groups is enabled by visible-light photoredox catalysis.

  通过可见光光合还原催化，实现了烷基三氟硼酸酯的基团脱硼氰化反应，适用于具有广泛功能基团的化合物。
• Formaldehyde Dialkylhydrazones as Neutral Formyl Anion and Cyanide Equivalents:  Nucleophilic Addition to Conjugated Enones
  作者：Elena Díez、Rosario Fernández、Consolación Gasch、José M. Lassaletta、José M. Llera、Eloísa Martín-Zamora、Juan Vázquez

  DOI：10.1021/jo970481d

  日期：1997.7.1

  A versatile methodology for the nucleophilic formylation and cyanation of conjugated enones is reported. The procedure is based on the use of formaldehyde dimethylhydrazone, which, acting as a neutral formyl anion equivalent, adds to preformed trialkylsilyl-enone complexes. Both 4-(silyloxy)-3-enal hydrazones 3 or deprotected 4-oxo aldehyde monohydrazones 4 can be obtained as products depending on quenching conditions. In full analogy, an asymmetric version of the reaction using chiral formaldehyde SAMP-hydrazone as a neutral synthon of the chiral formyl anion has been developed, giving rise to the corresponding adducts 5 and 6 in good yields and with excellent diastereoselectivities (de 85-greater than or equal to 98%). Ozonolysis or HCl-mediated hydrolysis of adducts 4 and 6 readily affords racemic and optically enriched 4-oxo aldehydes 7, respectively. Additionally, high-yielding MMPP-oxidative cleavage of 4-oxo hydrazones 4 and 6 has been performed to obtain Li-oxo nitriles 8 in racemic and optically enriched forms, respectively. In this way, interesting chiral bifunctional building blocks, some of them bearing newly created stereogenic quaternary centers, have been efficiently synthesized.
• Syntheses of nitrile and methyl ester corresponding to (dl)-sarkomycin and of related compounds
  作者：Jacques Froissant、Joëlle Vidal、Eryka Guibé-Jampel、Francois Huet

  DOI：10.1016/s0040-4020(01)89959-2

  日期：1987.1

  3-trimethylsiloxy 2-cycloalkene carbonitriles. Their alkylation with chloromethyl phenyl sulfide followed by oxone oxidation to sulfones and sulfinic acid elimination on basic alumina led to α-methylene carbonyl compounds. Obtention of the ester involved acetalization of 3-oxo 2-phenylthiomethyl cyclopentane carbonitrile, basic hydrolysis into acid, deacetalization, estenfication, oxidation and elimination of sulfinic

  腈和酯对应于（DL）-sarkomycin，6-和7-元环类似物腈，和3-甲基取代的腈制备。将氰基三甲基硅烷共轭添加到环状α-烯酮中，得到3-三甲基甲硅烷氧基2-环烯烃腈。它们用氯甲基苯硫醚进行烷基化，然后将酮氧化成砜，然后在碱性氧化铝上消除亚磺酸，生成α-亚甲基羰基化合物。获得该酯涉及3-氧代2-苯基硫代甲基环戊烷腈的缩醛化，碱性水解成酸，脱缩醛化，酯化，氧化和消除亚磺酸。