6-乙酰氧基-1-环己烯-1-甲腈 | 130251-99-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 6-乙酰氧基-1-环己烯-1-甲腈
• 英文名称: Acetoxy-6 cyano-1 cyclohexene
• 英文别名: 6-acetoxy-1-cyclohexene-1-carbonitrile；(2-Cyanocyclohex-2-en-1-yl) acetate
• CAS: 130251-99-9
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: LZIVYNHDVSDJOE-UHFFFAOYSA-N

物化性质

• 沸点：
  264.8±40.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-乙酰氧基-1-环己烯-1-甲腈 在 sodium 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 20.0h， 生成 6-acetylcyclohex-1-enecarbonitrile
  参考文献：
  名称：

  Synthesis of 5- and 6-Acyl-1-cyano and -1-ethoxycarbonyl Cycloalkenes

  摘要：

  Conjugated addition of primary nitroalkanes to the functional acetates 3 and 4 in basic medium, leads to the cyclic nitroesters 5 and nitronitriles 6. These derivatives are easily converted via the Nef reaction to the corresponding gamma-ketoestesrs 7 and gamma-ketonitriles 8 in good yields.

  DOI：

  10.1081/scc-120023510
• 作为产物：
  描述：

  6-乙酰氧基环己烯-1-羧酸乙酯 生成 6-乙酰氧基-1-环己烯-1-甲腈
  参考文献：
  名称：

  AMRI, HASSEN;RAMBAUD, MONIQUE;VILLIERAS, JEAN, TETRAHEDRON, 46,(1990) N0, C. 3535-3546

  摘要：

  DOI：

文献信息

• Substitution nucleophile d'acetates de cyclenols allyliques fonctionnels par des organometalliques en presence de sels cuivreux. Application a une synthese rapide de la (±)mitsugashiw alactone
  作者：Hassen Amri、Monique Rambaud、Jean Villieras

  DOI：10.1016/s0040-4020(01)81522-2

  日期：1990.1

  Substitution of functional allylic cycloalkenol acetates by Grignard reagents (primary , secondary, tertiary-alkyl, vinyl, aryl) in the presence of a catalytic amount (2.5% equivalent) of cuprous iodide at low temperature, gives high yields of various functional α-substituted cycloalkenes . The reaction can be applied to lithium enolates of esters and need no catalyst, but may be performed with HMPA

  在低温下在催化量（2.5％当量）的碘化亚铜存在下，用格氏试剂（伯，仲，叔烷基，乙烯基，芳基）取代功能性烯丙基环烯醇乙酸酯，可获得高产率的各种功能性α-取代的环烯烃。该反应可以应用于酯的烯醇锂，并且不需要催化剂，但是可以在HMPA作​​为助溶剂的情况下进行。它是由2，5-二甲氧基四氢呋喃完成的短（6步）高效有效的全选择性合成（±）-mitsugashiwalactone的例证，总收率为33％。
• Efficient Palladium-Catalyzed Nucleophilic Addition of Triorganoindium Reagents to Carbocyclic Derivatives
  作者：Lucas Baker、Thomas Minehan

  DOI：10.1021/jo0357162

  日期：2004.5.1

  Palladium (0)-catalyzed allylic substitution reactions employing triorganoindium reagents have been investigated. In situ generated vinyl- and arylindiums react with substituted and unsubstituted cyclohex-2-enyl esters in the presence of 1-3 mol % Pd-2(dba)(3) to produce vinyl- or arylcyclohexenes in moderate to excellent yields. The stereoselectivity of this process was also examined, and evidence is presented that the reaction proceeds with inversion of stereochemical configuration.
• Short Synthesis of Functionalized Cyclic Homoallylsilanes
  作者：Rim Ouled Saad、Taoufik Turki、Hassen Amri

  DOI：10.1080/00397910500297370

  日期：2005.11

  The synthesis of functionalized cyclic homoallylsilanes 5 and 6 was described starting from functional cycloalkenols 1 and 2, in which the addition of silylcuprate to the functional acetates 3 and 4 were used as the key reaction step.