2-benzoyl-3-phenyl-pent-4-enoic acid ethyl ester | 422270-77-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 2-benzoyl-3-phenyl-pent-4-enoic acid ethyl ester
• 英文别名: ethyl 2-benzoyl-3-phenylpent-4-enoate；Ethyl 2-benzoyl-3-phenylpent-4-enoate
• CAS: 422270-77-7
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: SSVISKVNNJLBFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzoyl-3-phenyl-pent-4-enoic acid ethyl ester 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.67h， 生成 (1R,2S)-1-phenyl-2-((R)-1-phenylallyl)propane-1,3-diol
  参考文献：
  名称：

  金（I）/手性N，N'-二氧化物-镍（II）中继催化不对称串联分子间氢烷氧基化/克莱森重排

  摘要：

  已经实现了炔基酯和烯丙基醇之间的高效不对称级联反应。成功的关键是由π-酸性金（I）配合物催化的加氢烷氧基化反应与由手性Lewis酸性N，N'-二氧化物-镍（II）配合物催化的Claisen重排的结合。在温和的反应条件下，以高收率（高达99：3）和良好的非对映选择性（高达97：3）和出色的对映选择性（高达99％ee）合成了一系列无环α-烯丙基β-酮酸酯 。这些产品可以轻松转化为光学活性的β-羟基酯，β-羟基酸或1,3-二醇。

  DOI：

  10.1002/anie.201611214
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 在 哌啶 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 8.0h， 生成 2-benzoyl-3-phenyl-pent-4-enoic acid ethyl ester
  参考文献：
  名称：

  A new route to 2-alkenyl-1,3-dicarbonyl compounds, intermediates in the synthesis of dihydrofurans

  摘要：

  A two step synthetic strategy for obtaining 2-alkenyl-1,3-dicarbonyl compounds from the corresponding 1,3-dicarbonyl compounds is reported. The method is based on a Knoevenagel condensation and a Michael addition using a high order organocuprate procedure, and proves to be of general value, Obtained compounds are useful starting materials for the synthesis of furan derivatives, (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01173-5

文献信息

• Copper-Catalyzed Cross-Coupling of Allylboronic Acids with α-Diazoketones
  作者：Arindam Das、Dong Wang、Marie-Charlotte Belhomme、Kálmán J. Szabó

  DOI：10.1021/acs.orglett.5b02285

  日期：2015.10.2

  Copper-catalyzed cross-coupling of substituted allylboronic acids with alpha-diazoketones was studied. This allylation reaction is highly regioselective, providing the branched allylic product. The process involves creation of a new C(sp(3))-C(sp(3)) bond by retaining the keto functional group of the alpha-diazoketone precursor.
• Iodoenolcyclization of 2-Allyl Substituted b-Keto Esters under Thermodynamic Conditions
  作者：Roberto Antonioletti、Savina Malancona、Paolo Bovicelli

  DOI：10.3987/com-04-10081

  日期：——

  An improved procedure for the synthesis of diastereo-enriched tetrasubstituted 4,5-dihydrofurans by using I-2-induced enolcyclization of beta-keto esters is reported. The reactions using I-2 in anhydrous MeCN are considered under thermodynamic control and the more stable trans isomers are preferentially produced.
• Diastereoselective synthesis of 4,5-dihydrofurans by iodoenolcyclisation of 2-allyl-1,3-dicarbonyl compounds
  作者：Roberto Antonioletti、Savina Malancona、Paolo Bovicelli

  DOI：10.1016/s0040-4020(02)01064-5

  日期：2002.10

  A study of the stereochemical aspects of I-2-induced cyclisation of 2-alkenyl-1,3-dicarbonyl compounds reveals that the iodoenolcyclisation is strictly dependent on the dicarbonyl species and the substituents in the allylic position. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Gold(I)/Chiral <i>N</i> , <i>N′</i> ‐Dioxide–Nickel(II) Relay Catalysis for Asymmetric Tandem Intermolecular Hydroalkoxylation/Claisen Rearrangement
  作者：Jun Li、Lili Lin、Bowen Hu、Pengfei Zhou、Tianyu Huang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/anie.201611214

  日期：2017.1.16

  efficient asymmetric cascade reaction between alkynyl esters and allylic alcohols has been realized. Key to success was the combination of a hydroalkoxylation reaction catalyzed by a π‐acidic gold(I) complex with a Claisen rearrangement catalyzed by a chiral Lewis acidic N,N′‐dioxide–nickel(II) complex. A range of acyclic α‐allyl β‐keto esters were synthesized in high yields (up to 99 %) with good

  已经实现了炔基酯和烯丙基醇之间的高效不对称级联反应。成功的关键是由π-酸性金（I）配合物催化的加氢烷氧基化反应与由手性Lewis酸性N，N'-二氧化物-镍（II）配合物催化的Claisen重排的结合。在温和的反应条件下，以高收率（高达99：3）和良好的非对映选择性（高达97：3）和出色的对映选择性（高达99％ee）合成了一系列无环α-烯丙基β-酮酸酯 。这些产品可以轻松转化为光学活性的β-羟基酯，β-羟基酸或1,3-二醇。
• A new route to 2-alkenyl-1,3-dicarbonyl compounds, intermediates in the synthesis of dihydrofurans
  作者：Roberto Antonioletti、Paolo Bovicelli、Savina Malancona

  DOI：10.1016/s0040-4020(01)01173-5

  日期：2002.1

  A two step synthetic strategy for obtaining 2-alkenyl-1,3-dicarbonyl compounds from the corresponding 1,3-dicarbonyl compounds is reported. The method is based on a Knoevenagel condensation and a Michael addition using a high order organocuprate procedure, and proves to be of general value, Obtained compounds are useful starting materials for the synthesis of furan derivatives, (C) 2002 Elsevier Science Ltd. All rights reserved.