1,1,2-三苯基-丁-1,3-二烯 | 82867-26-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1,1,2-三苯基-丁-1,3-二烯
• 英文名称: 1,1,2-triphenyl-buta-1,3-diene
• 英文别名: 1,1,2-Triphenyl-buta-1,3-dien；1,1,2-Triphenylbutadiene；1,1-diphenylbuta-1,3-dien-2-ylbenzene
• CAS: 82867-26-3
• 化学式: C₂₂H₁₈
• 分子量: 282.385
• InChiKey: QHJXOJHVTGXCRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1,1-diphenyl-2-iodo-4-(phenylselenyl)-1-butene 在 palladium diacetate 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 1,1,2-三苯基-丁-1,3-二烯
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling Reactions of 2-Iodo-4-(phenylchalcogenyl)-1-butenes

  摘要：

  2-Iodo-4-(phenylchalcogenyl)-1-butenes 2 or 3, which are derived from the ring-opening reaction of methylenecyclopropanes (MCPs) I by iodine, can be applied to some palladium-catalyzed cross-coupling reactions such as the Sonogashira, Heck, Kumada, Suzuki, and Negisbi reactions under mild conditions to give the corresponding coupling products in good yields. These reactions proceeded smoothly at room temperature (20 degrees C) in most cases without any phosphine ligand and additive. The phenylchalcogenyl group plays an important role in the reactions and a plausible reaction mechanism has been proposed.

  DOI：

  10.1021/jo051709x

文献信息

• Facile synthesis of multisubstituted buta-1,3-dienes via Suzuki–Miyaura and Kumada cross-coupling strategy of 2,4-diiodo-buta-1-enes with arylboronic acids and Grignard reagents
  作者：Li-Xiong Shao、Min Shi

  DOI：10.1039/b504071j

  日期：——

  One-pot Suzuki–Miyaura-type and Kumada-type cross-coupling reactions of 2,4-diiodo-buta-1-enes with arylboronic acids and alkyl/aryl magnesium bromides were carried out in the presence of accessibly simple catalysts under mild conditions. As a result, some 1,1,2-trisubstituted buta-1,3-dienes were obtained including the Tamoxifen-type, which have potential adjuvant therapy in women who have suffered from breast cancer and cyclooxygenase-2-type (COX-2-type) inhibitors, some of which have been proved to elicit efficient anti-inflammatory analgesic activities and less adverse gastrointestinal side effects and to be very useful in the prophylactic treatment of a wide variety of cancers and neurodegenerative disorders.

  在温和条件下，使用易得的简单催化剂，进行了2,4-二碘丁-1-烯与芳基硼酸和烷基/芳基溴化镁的单锅铃木-宫浦反应和熊田反应。因此，获得了一些1,1,2-三取代的丁-1,3-二烯，包括他莫昔芬类物质，这些物质在经历过乳腺癌的女性中具有潜在的辅助治疗效果，以及环氧酶-2类（COX-2类）抑制剂，其中一些已被证明具有有效的抗炎镇痛活性，并且不良的胃肠道副作用较少，且在多种癌症和神经退行性疾病的预防性治疗中非常有用。
• Coupling reaction of alkenylzirconocenes with aryl or alkenyl iodides in the presence of
  作者：Ryuichiro Hara、Yasushi Nishihara、Philippe D. Landré、Tamotsu Takahashi

  DOI：10.1016/s0040-4039(96)02322-2

  日期：1997.1

  Trisubstituted alkenylalkoxyzirconocenes which have been prepared from carbozirconation reactions of internal alkynes via zirconacyclopentenes reacted with aryl or alkenyl iodides in the presence of CuCl and a catalytic amount of Pd(PPh(3))(4) to give coupling products. Copyright (C) 1996 Elsevier Science Ltd
• Palladium-Catalyzed Cross-Coupling Reactions of 2-Iodo-4-(phenylchalcogenyl)-1-butenes
  作者：Min Shi、Le-Ping Liu、Jie Tang

  DOI：10.1021/jo051709x

  日期：2005.12.1

  2-Iodo-4-(phenylchalcogenyl)-1-butenes 2 or 3, which are derived from the ring-opening reaction of methylenecyclopropanes (MCPs) I by iodine, can be applied to some palladium-catalyzed cross-coupling reactions such as the Sonogashira, Heck, Kumada, Suzuki, and Negisbi reactions under mild conditions to give the corresponding coupling products in good yields. These reactions proceeded smoothly at room temperature (20 degrees C) in most cases without any phosphine ligand and additive. The phenylchalcogenyl group plays an important role in the reactions and a plausible reaction mechanism has been proposed.