4-phenyl-(Z)-2-pentene | 84519-66-4

• 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: 4-phenyl-(Z)-2-pentene
• 英文别名: [(Z,2S)-pent-3-en-2-yl]benzene
• CAS: 84519-66-4
• 化学式: C₁₁H₁₄
• 分子量: 146.232
• InChiKey: RSNZJWXIEBZSTE-NXSJDDFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-phenyl-(Z)-2-pentene 在 palladium diacetate 高氯酸 、 水 、 对苯醌 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 (S)-4-phenylpentan-2-one
  参考文献：
  名称：

  Palladium(II)-Catalyzed Exchange and Isomerization Reactions. 17. Exchange of Chiral Allyl Alcohols with Hydroxide, Methoxide, and Phenyl at High [Cl^-]. Stereochemistry of the Wacker Reaction

  摘要：

  At high [Cl-] (> 2.0 M), PdCl42- catalyzes the exchange of chiral allylic alcohols with hydroxy, methoxy, and phenyl to give chiral allyl-substituted olefins. With unsymmetrical olefins, isomerization occurs along with exchange. The hydroxyl exchange occurs in aqueous solution while the other exchanges are carried out in methanol solution. At low [Cl-] (0.1 M) oxidation to the corresponding beta-hydroxy-, methoxy-, and phenyl-substituted carbonyl compounds occurred. The absolute configurations of the oxidation and exchange products should be the same if the same mode of addition to the Pd(II)-pi-complex is operative. The absolute configurations of the oxidation and exchange products for the phenylation reaction were the same, while for hydroxy and methoxy they were different. This result indicates methanol and water must have different stereochemistries of addition at high and low [Cl-]. Thus, previous studies showing anti hydroxypalladation at high [Cl-] are not valid indicators of the stereochemistry at low [Cl-]. If anti addition occurs at high [Cl-], the addition must be syn at low [Cl-].

  DOI：

  10.1021/jo9906274
• 作为产物：
  描述：

  (Z)-pent-3-en-2-ol 、 氯化苯汞 在 palladium dichloride 作用下， 以 甲醇 为溶剂， 生成 [(Z,2R)-pent-3-en-2-yl]benzene 、 4-phenyl-(Z)-2-pentene
  参考文献：
  名称：

  Wacker反应的立体化学：高和低[Cl（-）]时氢氧化物，甲醇盐和苯基的加成模式。使用手性转移的研究。

  摘要：

  DOI：

  10.1021/jo971051q

文献信息

• Alkylation of allylic derivatives. 4. On the mechanism of alkylation of allylic N-phenylcarbamates with lithium dialkylcuprates
  作者：Harlan L. Goering、Steven S. Kantner、Chung Chyi Tseng

  DOI：10.1021/jo00153a019

  日期：1983.3
• GOERING, H. L.;KANTNER, S. S.;TSENG, CHUNG, CHYI, J. ORG. CHEM., 1983, 48, N 5, 715-721
  作者：GOERING, H. L.、KANTNER, S. S.、TSENG, CHUNG, CHYI

  DOI：——

  日期：——
• Palladium(II)-Catalyzed Exchange and Isomerization Reactions. 17. Exchange of Chiral Allyl Alcohols with Hydroxide, Methoxide, and Phenyl at High [Cl^-]. Stereochemistry of the Wacker Reaction
  作者：Othman Hamed、Patrick M. Henry、Charles Thompson

  DOI：10.1021/jo9906274

  日期：1999.10.1

  At high [Cl-] (> 2.0 M), PdCl42- catalyzes the exchange of chiral allylic alcohols with hydroxy, methoxy, and phenyl to give chiral allyl-substituted olefins. With unsymmetrical olefins, isomerization occurs along with exchange. The hydroxyl exchange occurs in aqueous solution while the other exchanges are carried out in methanol solution. At low [Cl-] (0.1 M) oxidation to the corresponding beta-hydroxy-, methoxy-, and phenyl-substituted carbonyl compounds occurred. The absolute configurations of the oxidation and exchange products should be the same if the same mode of addition to the Pd(II)-pi-complex is operative. The absolute configurations of the oxidation and exchange products for the phenylation reaction were the same, while for hydroxy and methoxy they were different. This result indicates methanol and water must have different stereochemistries of addition at high and low [Cl-]. Thus, previous studies showing anti hydroxypalladation at high [Cl-] are not valid indicators of the stereochemistry at low [Cl-]. If anti addition occurs at high [Cl-], the addition must be syn at low [Cl-].
• Stereochemistry of the Wacker Reaction:  Modes of Addition of Hydroxide, Methoxide, and Phenyl at High and Low [Cl^-]. A Study Using Chirality Transfer
  作者：Othman Hamed、Charles Thompson、Patrick M. Henry

  DOI：10.1021/jo971051q

  日期：1997.10.1