4-(2-oxocyclohexyl)butanenitrile | 82257-44-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-oxocyclohexyl)butanenitrile
• CAS: 82257-44-1
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: FSTBXMCHVPGFRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-oxocyclohexyl)butanenitrile 在 [RuH2(PPh3)4] 水 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 以41%的产率得到2-azabicyclo<5.4.0>undec-1(7)-en-3-one
  参考文献：
  名称：

  钌催化的腈水合反应和δ-酮腈向烯内酰胺的转化：（-）-pumiliotoxin C的全合成

  摘要：

  通过使用RuH 2（PPh 3）4催化剂生成相应的酰胺，可以有效地用1-2当量的水进行腈水合。在相似的反应条件下，δ-乙腈可以转化为相应的烯-内酰胺，它们是通用的合成中间体。通过（-）-pumiliotoxin C的短步合成证明了反应的效率。

  DOI：

  10.1016/s0040-4020(01)81902-5
• 作为产物：
  描述：

  (4E,5S)-4-hydroxyiminospiro[4.5]decan-10-one 在 titanium(III) chloride 、 ammonium acetate 作用下， 以 水 、 丙酮 为溶剂， 以75%的产率得到4-(2-oxocyclohexyl)butanenitrile
  参考文献：
  名称：

  路易斯酸催化结构相关的α，β-不饱和环氧酮和肟的重排。合成1,4-二酮螺[n，m]烷烃异构体的补充方法。

  摘要：

  路易斯酸催化α的重排，β环氧肟前进通过环氧乙烷裂解α与话务员频哪醇型烷基迁移到谐振肟部分中C稳定化的碳正离子α，得到1,3-二酮单肟。

  DOI：

  10.1016/s0040-4039(00)84850-9

文献信息

• Cyclic Alkenenitriles:  Chemoselective Oxonitrile Cyclizations
  作者：Fraser F. Fleming、Lee A. Funk、Ramazan Altundas、Vaqar Sharief

  DOI：10.1021/jo026396+

  日期：2002.12.1

  tert-butoxide triggers the chemoselective cyclization between nitrile anions and remote, enolizable carbonyl groups, despite the acidity difference favoring enolate formation and addition to the nitrile group. Domino deprotonation, cyclization, and dehydration efficiently transform a diverse array of omega-oxonitriles into carbocyclic and heterocyclic five- and six-membered alkenenitriles in a single synthetic

  尽管酸度差异有利于烯醇化物的形成和添加到腈基上，但是叔丁醇钾触发了腈阴离子与远端可烯醇化羰基之间的化学选择性环化。多米诺骨牌的去质子化，环化和脱水可在一次合成操作中有效地将多种ω-恶腈转化为碳环和杂环五元和六元烯腈。
• Electroreductive intramolecular coupling of γ- and δ-cyanoketones
  作者：Tatsuya Shono、Naoki Kise

  DOI：10.1016/s0040-4039(00)88791-2

  日期：1990.1

  Electroreduction of γ- and δ-cyanoketones in i-PrOH gave cyclized products α-hydroxyketones and their dehydroxylated ketones, and this reaction was applied to the synthesis of dihydrojasmone, methyl dihydrojasmonate, and Rosaprostol.

  在i-PrOH中电还原γ-和δ-氰基酮，生成环化产物α-羟基酮及其脱羟基酮，并将该反应用于二氢茉莉酮，二氢茉莉酮酸甲酯和Rosaprostol的合成。
• Cp2TiPh-coordinated cyano and ester groups as efficient ketyl radical acceptors in the reductive radical cyclization of γ- and δ-cyano ketones and δ-keto esters
  作者：Yoshihiko Yamamoto、Daisuke Matsumi

  DOI：10.1039/a800661j

  日期：——

  Cp2TiPh promotes the reductive radical cyclization of γ- and δ-cyano ketones and δ-keto esters to give α-hydroxycycloalkanones in moderate to good yields; the titanium reagent coordinates to both the ketone and the cyano or ester terminus, the LUMO of the cyano or ester group is thus lowered, and cyclization proceeds irreversibly without formation of the unstable iminyl or alkoxy radical intermediates.

  Cp2TiPh促进了γ-和δ-氰基酮及δ-酮酯的还原自由基环化，得到α-羟基环状酮，产率适中到良好；钛试剂与酮和氰基或酯末端均形成配位，氰基或酯基团的LUMO因此降低，环化过程不可逆进行，不会形成不稳定的亚胺或烷氧自由基中间体。
• Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Naoto Tominaga、Hiroshi Morita

  DOI：10.1021/jo00052a036

  日期：1992.12

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.
• Synthesis of 1,6-heterosubstituted products via radicals
  作者：Bernd Giese、Hans Horler、Wolfgang Zwick

  DOI：10.1016/s0040-4039(00)86986-5

  日期：1982.1