3-[1-hydroxy-1-(2-bromophenyl)methyl]-3-buten-2-one

• 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-hydroxy-1-(2-bromophenyl)methyl]-3-buten-2-one
• 英文别名: 3-[(2-bromo-phenyl)(hydroxy)methyl]but-3-en-2-one；3-[(2-Bromophenyl)-hydroxymethyl]but-3-en-2-one
• 化学式: C₁₁H₁₁BrO₂
• 分子量: 255.111
• InChiKey: VFYBBWZJZKUSRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[1-hydroxy-1-(2-bromophenyl)methyl]-3-buten-2-one 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (Z)-3-(bromomethyl)-4-(2-bromophenyl)but-3-en-2-one
  参考文献：
  名称：

  一种高效且简单的合成高度官能化化合物的策略

  摘要：

  摘要 描述了带有烯烃、硫烷基或胺功能的（（β-乙氧基羰基、-氰基和-乙酰基）丙氧基）甲基膦酸酯支架的小型文库的便利合成。所有这些新的衍生物易于从以下冷凝的三步反应序列容易获得的起始试剂（醛，贫电子烯烃，和dialkylphosphites）中产生，S Ñ 2'-型反应和缀合硫杂或氮杂-迈克尔1， 4-与芳香族和脂肪族硫醇或胺亲核试剂的加成。

  DOI：

  10.1080/10426507.2021.1948850
• 作为产物：
  描述：

  丁烯酮 、 邻溴苯甲醛 在 三乙烯二胺 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以81%的产率得到3-[1-hydroxy-1-(2-bromophenyl)methyl]-3-buten-2-one
  参考文献：
  名称：

  由2-溴联苯甲醛的森田-贝利斯-希尔曼加合物合成吡唑并[4,3-c]喹啉

  摘要：

  吡唑并[4,3– c ]喹啉的合成是从森田—贝利斯—希尔曼的2-溴苯甲醛和甲基乙烯基酮的溴化物中进行的。该合成涉及从α，β-烯酮一锅法制备官能化吡唑的新方法，一锅Cu介导的分子内N-芳基化作用以及对甲苯磺酸的消除。

  DOI：

  10.1002/bkcs.10050

文献信息

• Proline-Mediated Baylis–Hillman Reaction of Methyl Vinyl Ketone without a Co-catalyst under Solvent-Free Conditions
  作者：Srinivasan Easwar、Heena Inani、Ajit Jha

  DOI：10.1055/s-0036-1588320

  日期：——

  A proline-mediated Baylis–Hillman reaction of methyl vinyl ketone with aromatic aldehydes has been carried out without using any co-catalyst, under solvent-free conditions. The reaction works efficiently at 60 °C in the presence of a small amount of water to afford the Baylis–Hillman adducts in reasonable to very good yields over 8–48 h. The absence of a co-catalyst suggests that proline plays a role

  脯氨酸介导的甲基乙烯基酮与芳香醛的 Baylis-Hillman 反应已在无溶剂条件下进行，无需使用任何助催化剂。该反应在 60 °C 下在少量水存在下有效进行，以在 8-48 小时内以合理到非常好的产率提供 Baylis-Hillman 加合物。没有助催化剂表明脯氨酸除了参与亚胺离子形成和共轭加成外，还在反应机制的质子转移步骤中发挥作用。原则上，这意味着脯氨酸在反应中充当三功能催化剂，而对这方面更深入了解的机理研究应该会在未来提供进一步的见解。
• Synthesis of Unsaturated Seven-Membered Ring Lactams through Palladium-Catalyzed Amination and Intramolecular Cyclocarbonylation Reactions of Amines and Baylis−Hillman Acetates
  作者：Hong Cao、Tiago O. Vieira、Howard Alper

  DOI：10.1021/ol102699a

  日期：2011.1.7

  A versatile synthesis of unsaturated seven-membered ring lactams has been developed. The sequence involves hydroamination of Baylis−Hillman acetate with amines, followed by intramolecular cyclocarbonylation reactions of the resulting allylamines. This process can tolerate a wide array of functional groups, and affords lactams in excellent yields.

  已经开发了不饱和七元环内酰胺的通用合成方法。该序列包括用胺对Baylis-Hillman乙酸酯进行加氢胺化，然后进行所得烯丙胺的分子内环羰基化反应。该过程可以耐受各种各样的官能团，并以优异的产率提供内酰胺。
• 1-Methylimidazole 3-N-oxide as a new promoter for the Morita–Baylis–Hillman reaction
  作者：Yu-Sheng Lin、Chih-Wei Liu、Thomas Y.R. Tsai

  DOI：10.1016/j.tetlet.2005.01.099

  日期：2005.3

  The Morita-Baylis-Hillman reaction of aldehydes with alpha,beta-unsaturated ketones can be affected by the Lewis bases. We have found that 1-methylimidazole 3-N-oxide promoted the Morita-Baylis-Hiliman reaction of various activated aldehyde compounds in non-solvent system. This is a mild reaction condition and requires no special equipment to give the Morita-BaylisHillman adducts. (C) 2005 Elsevier Ltd. All rights reserved.
• Patil, Nitin R.; Kshirsagar, Siddheshwar W.; Samant, Shriniwas D., Journal of the Indian Chemical Society, 2013, vol. 90, # 10, p. 1703 - 1712
  作者：Patil, Nitin R.、Kshirsagar, Siddheshwar W.、Samant, Shriniwas D.

  DOI：——

  日期：——
• Formation of Cyclohepta[<i>b</i>]indole Scaffolds via Heck Cyclization: A Strategy for Structural Analogues of Ervatamine Group of Indole Alkaloid
  作者：Progyashree Goswami、Arun Jyoti Borah、Prodeep Phukan

  DOI：10.1021/jo502443a

  日期：2015.1.2

  Ervatamine, silicine, methuenine, etc., are naturally occurring alkaloids that exhibit antimicrobial, anticancer, and anti-HIV activities. Indole fused with a seven-membered carbocyclic ring is a commonly observed structural feature among this series of bioactive compounds. This work describes a strategic approach for the synthesis of cyclohepta[b]indole structural scaffolds. The synthetic strategy consists of a solvent-free Baylis-Hillman reaction of 2-bromobenzaldehydes, followed by iodine-catalyzed C-alkylation of indole with the Baylis-Hillman adducts. Finally, intramolecular Heck coupling reaction using Pd(OAc)(2) as catalyst in the presence of benzyltrimethylammonium bromide under microwave condition produced the desired cyclohepta[b]indole derivatives.