(E)-1,5-diphenyl-2-(phenylsulfonyl)pent-4-en-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1,5-diphenyl-2-(phenylsulfonyl)pent-4-en-1-one
• 英文别名: (E)-2-acetyl-N,N-dimethyl-5-phenylpent-4-enamide；2-benzenesulfonyl-1,5-diphenyl-pent-4-en-1-one；2-benzenesulfonyl-1,5-diphenylpent-4-en-1-one；(E)-2-(benzenesulfonyl)-1,5-diphenylpent-4-en-1-one
• 化学式: C₂₃H₂₀O₃S
• 分子量: 376.476
• InChiKey: IXNLESHENDPLOL-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1,5-diphenyl-2-(phenylsulfonyl)pent-4-en-1-one 以83%的产率得到
  参考文献：
  名称：

  NAKAMURA, KAORU;FUJII, MASAYUKI;MEKATA, HIDEYUKI;OKA, SHINZABURO;OHNO, AT+, CHEM. LETT., 1986, N 1, 87-88

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(苯基磺酰)苯乙酮 、 3-苯基丙-2-烯-1-醇 在 四(三苯基膦)钯 1-金刚烷甲酸 作用下， 以 水 为溶剂， 反应 1.5h， 以99%的产率得到(E)-1,5-diphenyl-2-(phenylsulfonyl)pent-4-en-1-one
  参考文献：
  名称：

  碳亲核试剂的钯催化，羧酸辅助的烯丙基取代与烯丙醇在水中的烯丙基化剂。

  摘要：

  [结构：见正文]使用四（三苯基膦）钯和羧酸如1-金刚烷羧酸的组合已经实现了作为悬浮介质的水中烯丙醇的烯丙基取代。事实证明，各种底物可适用于该催化体系。

  DOI：

  10.1021/ol035126q

文献信息

• Allylation of Carbon Pronucleophiles with Alkynes in the Presence of Palladium/Acetic Acid Catalyst
  作者：Nitin T. Patil、Isao Kadota、Akinori Shibuya、Young Soo Gyoung、Yoshinori Yamamoto

  DOI：10.1002/adsc.200404046

  日期：2004.6

  efficient and eco-chemical process for the allylation of carbon pronucleophiles with alkynes. The reaction of alkynes with various active methynes and methylenes in the presence of Pd(PPh3)4/acetic acid gave the corresponding allylated products in high yields and high regioselectivities. In the present catalytic system, the key is the use of carboxylic acid which dramatically enhances the rate of the

  我们已经开发了一种有效的生态化学方法，用于将碳原核亲核体与炔烃烯丙基化。在Pd（PPh 3）4 /乙酸存在下，炔烃与各种活性亚甲基和亚甲基的反应以高收率和高区域选择性提供了相应的烯丙基化产物。在本催化体系中，关键是使用羧酸，其可大大提高反应速度。该过程的重要特征之一是既不释放离去基团，也不产生生成亲核试剂所需化学计量的碱。
• Palladium-Catalyzed, Carboxylic Acid-Assisted Allylic Substitution of Carbon Nucleophiles with Allyl Alcohols as Allylating Agents in Water
  作者：Kei Manabe、Shū Kobayashi

  DOI：10.1021/ol035126q

  日期：2003.9.1

  [structure: see text] Allylic substitution of allyl alcohols in water as a suspension medium has been realized using a combination of tetrakis(triphenylphosphine)palladium and a carboxylic acid such as 1-adamantanecarboxylic acid. Various substrates turned out to be applicable to this catalytic system.

  [结构：见正文]使用四（三苯基膦）钯和羧酸如1-金刚烷羧酸的组合已经实现了作为悬浮介质的水中烯丙醇的烯丙基取代。事实证明，各种底物可适用于该催化体系。
• An Improved Catalytic System, Pd(PPh₃)₄/PhCOOH Combined Catalyst, for the Allylation of Carbon Pronucleophiles with Allenes
  作者：Yoshinori Yamamoto、Nitin T. Patil、Nirmal K. Pahadi

  DOI：10.1055/s-2004-829178

  日期：——

  The reaction of allenes with active methynes and methylenes proceeded smoothly in the presence of Pd(PPh3)4/PhCOOH combined catalyst to give the corresponding monoallylated products with E-stereoselectivity in good to high yields. This result is in marked contrast to the previous finding that the reaction of allenes with active methynes, in the presence of Pd2(dba)3·CHCl3/dppb catalyst, affords the allylation products in lower yield with lower stereoselectivities.

  在Pd(PPh3)4/PhCOOH联合催化剂的存在下，烯炔与活性烯烃和亚烯的反应顺利进行，生成相应的单烯基化产物，具有E-立体选择性，产率良好到高。这一结果与之前的发现形成鲜明对比，即在Pd2(dba)3·CHCl3/dppb催化剂的存在下，烯炔与活性烯烃的反应所得到的烯基化产物产率较低且立体选择性较差。
• Direct allylic substitution of allyl alcohols by carbon pronucleophiles in the presence of a palladium/carboxylic acid catalyst under neat conditions
  作者：Nitin T. Patil、Yoshinori Yamamoto

  DOI：10.1016/j.tetlet.2004.02.094

  日期：2004.4

  The reaction of allylic alcohols with carbon pronucleophiles in the presence of the Pd(PPh3)4/carboxylic acid combined catalytic system, under neat conditions (without an organic solvent or without water as the solvent) enabled the direct allylation of the pronucleophiles, giving the corresponding allylated products in high yields.

  在纯条件下（无有机溶剂或无水作为溶剂），在Pd（PPh 3）4 /羧酸联合催化体系存在下，烯丙醇与碳原核亲核试剂的反应使原核亲核试剂直接烯丙基化，得到相应的烯丙基化产品，收率很高。
• Microwave-assisted manganese(III) acetate based oxidative cyclizations of alkenes with β-ketosulfones
  作者：Christophe Curti、Maxime D. Crozet、Patrice Vanelle

  DOI：10.1016/j.tet.2008.10.080

  日期：2009.1

  The microwave-assisted synthesis of 5-(4-nitrophenyl)-2-phenyl-4-(phenylsulfonyl)-2,3-dihydrofuran (5a) was performed via manganese(Ill) acetate based oxidative cyclization of 1-(4-nitrophenyl)-2(phenylsulfonyl)ethanone (3a) with vinylbenzene (4a). This new protocol was applied to four sulfone derivatives (3a-d), using vinylbenzene (4a) and diphenylethene (4b), affording a series of 2,3-dihydrofurans (5a-d, 6a-d) in moderate to good yields (26-55%). Similar methodology, applied on allylbenzene (4c), surprisingly, led to dehydronaphthalene derivatives (7a-d) in moderate yields. The unexpected mechanism and the role of allylbenzene (4c) are herein discussed. (C) 2008 Elsevier Ltd. All rights reserved.