3-Cyclopentencarbonsaeureanilid | 128535-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Cyclopentencarbonsaeureanilid
• 英文别名: 2-cyclopentene-1-carboxanilide；cyclopent-2-enecarbanilide；Cyclopenten-(2)-carbonsaeure-(1)-anilid；Cyclopent-2-encarbanilid；2-Cyclopentene-1-carboxamide, N-phenyl-；N-phenylcyclopent-2-ene-1-carboxamide
• CAS: 128535-00-2
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: HFLMWLKMBBHUBB-UHFFFAOYSA-N

物化性质

• 沸点：
  377.2±31.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Cyclopentencarbonsaeureanilid 在 四氢呋喃 、 bis(1,5-cyclooctadiene)nickel (0) 、 70 deg C 、 硫酸 、 三环己基膦 作用下， 以86%的产率得到cyclopentene-1-(N-phenyl)carboxamide
  参考文献：
  名称：

  Eine Ni0-induzierte CC-kupplungsreaktion von phenylisocyanat mit cyclopenten in gegenwart von chiralen phosphor-liganden

  摘要：

  In the presence of chiral phosphite- and phosphonite-Ni-0-systems, cyclopentene reacts with phenylisocyanate to give optically active 2-cyclopentene-1-carboxanilide (2) by CC-coupling. Enantiomeric excesses of up to 13% have been obtained so far.As a competitive reaction, an isomerization of 2 occurs; this gives rise to a decrease in regioselectivity, The isomeric distribution in the final product mixture clearly shows a relationship between the tendency of isomerization and the basicity of the P-ligands.The product distribution, as well as the determination of enantiomeric excess, took place on GC, and the enantiomeric separation took place on HPLC.

  DOI：

  10.1016/0022-328x(96)06149-9
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 3-Cyclopentencarbonsaeureanilid
  参考文献：
  名称：

  Bokil; Nargund, Proceedings - Indian Academy of Sciences, Section A, 1940, vol. 11, p. 409,411

  摘要：

  DOI：

文献信息

• Neuartige Ni0-katalysierte Herstellung von 3-cyclopentencarbonsäureaniliden aus Cyclopentenen und Phenylisocyanat
  作者：Heinz Hoberg、Matthias Nohlen

  DOI：10.1016/0022-328x(90)85236-r

  日期：1990.2

  Cyclopentenes react with isocyanate on (Lig)Ni0-systems to form the bicyclic 5-azanickelacyclopentan-4-one derivates. The geometry of these butterfly complexes favors β-elimination of the β′-hydrogen atoms over that of the β- or β″-hydrogen. In a catalytic reaction the unsaturated amides 3-cyclopentene-carboxylic amide or 2-methylcyclopentene-3-carboxylic amide, both of which are substituted in position

  环戊烯与（Lig）Ni 0-系统上的异氰酸酯反应形成双环5-氮杂镍-环戊烷-4-一衍生物。这些蝶形配合物的几何形状比β-或β''-氢的β-氢原子更倾向于β-消除。在催化反应中，以高选择性形成在3位被取代的不饱和酰胺3-环戊烯-羧酸酰胺或2-甲基环戊烯-3-羧酸酰胺。
• Eine Ni0-induzierte CC-kupplungsreaktion von phenylisocyanat mit cyclopenten in gegenwart von chiralen phosphor-liganden
  作者：A. Tillack、R. Selke、Ch. Fischer、D. Bilda、K. Kortus

  DOI：10.1016/0022-328x(96)06149-9

  日期：1996.7

  In the presence of chiral phosphite- and phosphonite-Ni-0-systems, cyclopentene reacts with phenylisocyanate to give optically active 2-cyclopentene-1-carboxanilide (2) by CC-coupling. Enantiomeric excesses of up to 13% have been obtained so far.As a competitive reaction, an isomerization of 2 occurs; this gives rise to a decrease in regioselectivity, The isomeric distribution in the final product mixture clearly shows a relationship between the tendency of isomerization and the basicity of the P-ligands.The product distribution, as well as the determination of enantiomeric excess, took place on GC, and the enantiomeric separation took place on HPLC.
• Bokil; Nargund, Proceedings - Indian Academy of Sciences, Section A, 1940, vol. 11, p. 409,411
  作者：Bokil、Nargund

  DOI：——

  日期：——