3,3-bis(3-phenyl-2-propen-1-yl)pentane-2,4-dione | 106536-22-5

• 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: 3,3-bis(3-phenyl-2-propen-1-yl)pentane-2,4-dione
• 英文别名: 3,3-bis-(3-phenylprop-2-enyl)-pentane-2,4-dione；3,3-bis-(trans-cinnamyl)pentane-2,4-dione；3,3-dicinnamylpentane-2,4-dione；3,3-bis[(E)-3-phenylprop-2-enyl]pentane-2,4-dione
• CAS: 106536-22-5
• 化学式: C₂₃H₂₄O₂
• 分子量: 332.442
• InChiKey: ZBBDXUZCYXSPRJ-KAVGSWPWSA-N

物化性质

• 熔点：
  60-62 °C(Solvent: Ethanol)
• 沸点：
  526.1±50.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Cinnamyl bromide 、 乙酰丙酮 在 aluminum oxide 、 sodium ethanolate 作用下， 反应 3.0h， 以75%的产率得到3,3-bis(3-phenyl-2-propen-1-yl)pentane-2,4-dione
  参考文献：
  名称：

  Solvent-free synthesis of 4,4-bis-functionalized-1,6-dienes and 1,6-diynes on the surface of neutral alumina

  摘要：

  An improved procedure has been developed for the synthesis of structurally varied 4,4-bis-functionalized-1,6-dienes and 1,6-diynes through regioselective alkylation of active methylene compounds with several unsymmetrical allyl bromides and propargyl bromide on the surface of neutral alumina impregnated with sodium ethoxide or potassium tert-butoxide in the absence of any solvent under environmentally benign conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00896-1

文献信息

• Palladium catalyzed c-allylation of highly acidic carbo and heterocyclic β-dicarbonyl compounds
  作者：M. Prat、M. Moreno-Mañas、J. Ribas

  DOI：10.1016/s0040-4020(01)86091-9

  日期：1988.1

  Highly acidic carbo and heterocyclic β-dicarbonyl compounds such as barbituric acid, 3,5-dimethyl-2-1,2,6-thiadiazine 1,1-dioxide, cyclohexane-1,3-dione, tetronic acids, Meldrum acid and 1,2-diphenylpyrazolidine-3,5-dione are efficiently C-allylated with primary and secondary allylating agents under palladium catalysis.

  高酸性碳和杂环β-二羰基化合物，例如巴比妥酸，3,5-二甲基-2 -1,2,6-噻二嗪1,1-二氧化物，环己烷-1,3-二酮，四氢代酸，Meldrum酸和1在钯催化下，用伯和仲烯丙基化剂有效地将2--二苯基吡唑烷-3,5-二酮进行C-烯丙基化。
• Solvent-Controlled Highly Selective Bis- and Monoallylation of Active Methylene Compounds by Allyl Acetate with Palladium(0) Nanoparticle
  作者：Brindaban C. Ranu、Kalicharan Chattopadhyay、Laksmikanta Adak

  DOI：10.1021/ol702099v

  日期：2007.10.1

  catalyst for the allylation of active methylene compounds. Very efficient bisallylation is achieved for a variety of active methylene compounds by allyl acetate and its derivatives in one stroke in THF solvent. The reaction in water provides monoallylated product selectively by allyl acetate only. The recovered Pd(0) nanoparticle is recycled. A probable mechanism is suggested.

  钯（0）纳米颗粒已被用作有效的催化剂，用于活性亚甲基化合物的烯丙基化。在THF溶剂中，一次通过乙酸烯丙酯及其衍生物就可以对多种活性亚甲基化合物实现非常有效的双烯丙基化。在水中的反应仅通过乙酸烯丙酯选择性地提供单烯丙基化的产物。回收的Pd（0）纳米颗粒被回收。建议一种可能的机制。
• Dual Platinum and Pyrrolidine Catalysis in the Direct Alkylation of Allylic Alcohols: Selective Synthesis of Monoallylation Products
  作者：Ryozo Shibuya、Lu Lin、Yasuhito Nakahara、Kazushi Mashima、Takashi Ohshima

  DOI：10.1002/anie.201311200

  日期：2014.4.22

  A dual platinum‐ and pyrrolidine‐catalyzed direct allylic alkylation of allylic alcohols with various active methylene compounds to produce products with high monoallylation selectivity was developed. The use of pyrrolidine and acetic acid was essential, not only for preventing undesirable side reactions, but also for obtaining high monoallylation selectivity.

  开发了双铂和吡咯烷催化的烯丙基醇与各种活性亚甲基化合物的直接烯丙基烷基化反应，以生产具有高单烯丙基化选择性的产品。吡咯烷和乙酸的使用是必不可少的，不仅用于防止不良的副反应，而且用于获得高的单烯丙基化选择性。
• Palladium-catalysed nucleophilic release of allylic amines from a phenolic resin
  作者：Martyn Fisher、Richard C.D Brown

  DOI：10.1016/s0040-4039(01)01739-7

  日期：2001.11

  2° Allylic alcohols were coupled to phenolic polystyrene resin under Mitsunobu conditions to provide substituted allyl ethers, which underwent efficient nucleophilic cleavage by 1° and 2° amines in the presence of catalytic palladium to afford allylic amines.

  在Mitsunobu条件下，将2°烯丙醇与酚醛聚苯乙烯树脂偶联以提供取代的烯丙基醚，该烯丙基醚在催化钯存在下被1°和2°胺进行有效的亲核裂解，得到烯丙基胺。
• Micellar Catalysis Using a Photochromic Surfactant: Application to the Pd-Catalyzed Tsuji–Trost Reaction in Water
  作者：Muriel Billamboz、Floriane Mangin、Nicolas Drillaud、Carole Chevrin-Villette、Estelle Banaszak-Léonard、Christophe Len

  DOI：10.1021/jo401737t

  日期：2014.1.17

  The first example of a Pd-catalyzed Tsuji-Trost reaction, applied in a photochromic micellar media under conventional heating and microwave irradiation, is reported. The surfactant activity and recycling ability were investigated and compared with those of a few commercially available surfactants. The synthetic photochromic surfactant proved to be efficient, recyclable, and versatile for Pd-catalyzed coupling reactions.