3-(1-methylvinyl)-4-phenylpent-4-enal | 336185-52-5

• 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-(1-methylvinyl)-4-phenylpent-4-enal
• 英文别名: 4-Methyl-3-(1-phenylethenyl)pent-4-enal；4-methyl-3-(1-phenylethenyl)pent-4-enal
• CAS: 336185-52-5
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: NLSBUDYRDJUEKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(1-methylvinyl)-4-phenylpent-4-enal 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-Isopropenyl-4-phenyl-pent-4-en-1-ol
  参考文献：
  名称：

  Insight into the Rh-catalyzed cyclization of dissymmetrically racemic (±)-3,4-disubstituted 4-pentenal: regio-, diastereo-, enantioselectivity, and kinetic resolution

  摘要：

  Rh-Catalyzed cyclization was applied for the kinetic resolution of dissymmetrical (+/-)-3-(1-methylvinyl)-4-phenylpent-4-enal. The cyclization by a chiral neutral Rh[(S)-BINAP]Cl afforded a mixture of 3,4-cis-4-methylcyclopentanone (>95% ee, 19% yield), 3,4-trans-4-methylcyclopentanone, and 3,4-cis-4-phenylcyclopentanone (>95% ee, 21% yield). The cyclization by a cationic Rh[(R)-BINAP]ClO4 afforded a mixture of 3,4-trans-4-methylcyclopentanone (>95% ee, 36% yield), 3,4-cis-4-methyl-, and 3,4-trans-4-phenylcyclopentanone, accompanied with recovery of the starting material (-)-4-pentenal (54% ee, 34% yield), and by a cationic Rh[(S)BINAP]ClO4 afforded the corresponding enantiomers. The course of the cyclization and the stereochemistry of products are discussed based on the plausible acyl-hydride rhodium intermediates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01107-8
• 作为产物：
  描述：

  ethyl 4-methyl-3-(1-phenylvinyl)pent-4-enoate 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 1.0h， 以88%的产率得到3-(1-methylvinyl)-4-phenylpent-4-enal
  参考文献：
  名称：

  Insight into the Rh-catalyzed cyclization of dissymmetrically racemic (±)-3,4-disubstituted 4-pentenal: regio-, diastereo-, enantioselectivity, and kinetic resolution

  摘要：

  Rh-Catalyzed cyclization was applied for the kinetic resolution of dissymmetrical (+/-)-3-(1-methylvinyl)-4-phenylpent-4-enal. The cyclization by a chiral neutral Rh[(S)-BINAP]Cl afforded a mixture of 3,4-cis-4-methylcyclopentanone (>95% ee, 19% yield), 3,4-trans-4-methylcyclopentanone, and 3,4-cis-4-phenylcyclopentanone (>95% ee, 21% yield). The cyclization by a cationic Rh[(R)-BINAP]ClO4 afforded a mixture of 3,4-trans-4-methylcyclopentanone (>95% ee, 36% yield), 3,4-cis-4-methyl-, and 3,4-trans-4-phenylcyclopentanone, accompanied with recovery of the starting material (-)-4-pentenal (54% ee, 34% yield), and by a cationic Rh[(S)BINAP]ClO4 afforded the corresponding enantiomers. The course of the cyclization and the stereochemistry of products are discussed based on the plausible acyl-hydride rhodium intermediates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01107-8

文献信息

• Insight into the Rh-catalyzed cyclization of dissymmetrically racemic (±)-3,4-disubstituted 4-pentenal: regio-, diastereo-, enantioselectivity, and kinetic resolution
  作者：Masanori Imai、Masakazu Tanaka、Hiroshi Suemune

  DOI：10.1016/s0040-4020(00)01107-8

  日期：2001.2

  Rh-Catalyzed cyclization was applied for the kinetic resolution of dissymmetrical (+/-)-3-(1-methylvinyl)-4-phenylpent-4-enal. The cyclization by a chiral neutral Rh[(S)-BINAP]Cl afforded a mixture of 3,4-cis-4-methylcyclopentanone (>95% ee, 19% yield), 3,4-trans-4-methylcyclopentanone, and 3,4-cis-4-phenylcyclopentanone (>95% ee, 21% yield). The cyclization by a cationic Rh[(R)-BINAP]ClO4 afforded a mixture of 3,4-trans-4-methylcyclopentanone (>95% ee, 36% yield), 3,4-cis-4-methyl-, and 3,4-trans-4-phenylcyclopentanone, accompanied with recovery of the starting material (-)-4-pentenal (54% ee, 34% yield), and by a cationic Rh[(S)BINAP]ClO4 afforded the corresponding enantiomers. The course of the cyclization and the stereochemistry of products are discussed based on the plausible acyl-hydride rhodium intermediates. (C) 2001 Elsevier Science Ltd. All rights reserved.