ethyl 2-acetyl-2-(3-phenyl-2-propenyl)-5-phenyl-4-pentenoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: ethyl 2-acetyl-2-(3-phenyl-2-propenyl)-5-phenyl-4-pentenoate
• 英文别名: ethyl 3-oxo-2,2-bis-(3-phenylprop-2-enyl)-butanoate；2.2-di-trans-cinnamyl-acetoacetic acid ethyl ester；5t-Phenyl-2-trans-cinnamyl-2-acetyl-penten-(4)-saeure-(1)-aethylester；2.2-Di-trans-cinnamyl-acetessigsaeure-aethylester；ethyl (E)-2-acetyl-5-phenyl-2-[(E)-3-phenylprop-2-enyl]pent-4-enoate
• 化学式: C₂₄H₂₆O₃
• 分子量: 362.469
• InChiKey: QNQGBIMFGVFSCT-OTYYAQKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 Cinnamyl bromide 在 aluminum oxide 、 sodium ethanolate 作用下， 反应 3.0h， 以80%的产率得到ethyl 2-acetyl-2-(3-phenyl-2-propenyl)-5-phenyl-4-pentenoate
  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

• 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。
• (π-Allyl)palladium Complexes Bearing Diphosphinidenecyclobutene Ligands (DPCB):  Highly Active Catalysts for Direct Conversion of Allylic Alcohols
  作者：Fumiyuki Ozawa、Hideyuki Okamoto、Seiji Kawagishi、Shogo Yamamoto、Tatsuya Minami、Masaaki Yoshifuji

  DOI：10.1021/ja0274406

  日期：2002.9.1

  The (pi-allyl)palladium complex bearing an sp2-hybridized phosphorus ligand (DPCB-OMe: 1,2-bis(4-methoxyphenyl)-3,4-bis[(2,4,6-tri-tert-butylphenyl)phosphinidene]cyclobutene) efficiently catalyzes direct conversion of allylic alcohols in the absence of activating agents of alcohols such as Lewis acids. N-Allylation of aniline proceeds at room temperature to afford monoallylated anilines in 90-97% yields

  带有 sp2-杂化磷配体的（pi-烯丙基）钯配合物（DPCB-OMe：1,2-双（4-甲氧基苯基）-3,4-双[（2,4,6-三叔丁基苯基）在不存在醇（例如路易斯酸）的活化剂的情况下，膦亚基]环丁烯）有效地催化烯丙醇的直接转化。苯胺的 N-烯丙基化在室温下进行，以 90-97% 的产率得到单烯丙基化的苯胺。使用催化量的吡啶作为碱，活性亚甲基化合物的 C-烯丙基化也在 50 摄氏度下成功，以 85-95% 的产率得到单烯丙基化产物。涉及氢化和（π-烯丙基）钯中间体的催化机制已根据使用假定中间体的模型化合物进行的化学计量检验提出。
• 322. Migration of allyl groups in the ethyl acetoacetate series
  作者：Ernst Bergmann、Herbert Corte

  DOI：10.1039/jr9350001363

  日期：——
• Palladium(O)-catalyzed substitution of allylic substrates in an aqueous-organic medium
  作者：Errol Blart、Jean Pierre Geneˆt、Mohamed Safi、Monique Savignac、Denis Sinou

  DOI：10.1016/s0040-4020(01)80772-9

  日期：1994.1

  A palladium(0)-water soluble catalyst prepared in situ from palladium acetate and the sulfonated triphenyl phosphine P(C6H4-m-SO3Na)(3) (or tppts) is an efficient catalyst for allylic substitution with various carbon and heteronucleophiles in an aqueous-organic medium, allowing a very easy separation of the product(s) and the recycling of the catalyst.