(2-氰基环戊-2-烯-1-基)乙酸酯 | 130251-98-8

• 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: (2-氰基环戊-2-烯-1-基)乙酸酯
• 英文名称: Acetoxy-5 cyano-1 cyclopentene
• 英文别名: 1-Cyclopentene-1-carbonitrile, 5-(acetyloxy)-；(2-cyanocyclopent-2-en-1-yl) acetate
• CAS: 130251-98-8
• 化学式: C₈H₉NO₂
• 分子量: 151.165
• InChiKey: AOGMNSXUNYMONJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (2-氰基环戊-2-烯-1-基)乙酸酯 在 sodium hydroxide 、 sodium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 74.0h， 生成 5-propionylcyclopent-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：

  乙基5-羟基-1-环戊烯-1-羧酸酯 生成 (2-氰基环戊-2-烯-1-基)乙酸酯
  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％。
• 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.
• Elegant Synthesis of Highly Functionalized 1,2,3-Trisubstituted Cyclopentanes
  作者：Fatma Saâdi、Aïcha Arfaoui、Hassen Amri

  DOI：10.1080/00397911.2011.654371

  日期：2013.6.3

  The conversion of cyclic Baylis-Hillman acetates 1 into the corresponding cyano derivatives 2 was achieved using potassium cyanide in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) in aqueous medium. The obtained Michael acceptors 2 easily add primary amines in absolute ethanol to produce a new family of 1,2,3-trisubstituted cyclpentanes 3 in good yields.
• Synthesis of 5- and 6-Acyl-1-cyano and -1-ethoxycarbonyl Cycloalkenes
  作者：Houda Kraïem、Taoufik Turki、Hassen Amri

  DOI：10.1081/scc-120023510

  日期：2003.9

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

  DOI：——

  日期：——