ethyl (E)-2-methyl-5-phenylpent-2-enoate | 170233-98-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-2-methyl-5-phenylpent-2-enoate
• 英文别名: ethyl 2-methyl-5-phenyl-pent-2-enoate；Ethyl 2-methyl-5-phenylpent-2-enoate；ethyl 2-methyl-5-phenylpent-2-enoate
• CAS: 170233-98-4
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: YZHGFRNWBWXWKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-methyl-5-phenylpent-2-enoate 在 四氧化锇 、 N-甲基吲哚酮 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 48.0h， 生成 ethyl 2,2,4-trimethyl-5-(2-phenylethyl)-1,3-dioxolane-4-carboxylate
  参考文献：
  名称：

  钯催化的氧化环化反应：二氢吡喃酮和呋喃酮的合成

  摘要：

  将引起各种β-羟基烯酮的硼介导的顺式和反式立体选择性醛醇缩合反应与Pd （II）介导的氧化环化反应偶联，以高收率得到2,3,6-三取代的顺式和反式二氢吡喃酮。Pd （II）介导的氧化环化反应扩展为α-羟基烯酮，生成了呋喃3（2 H）-one衍生物，其中包括天然产物Bullatenone和已知的geiparvarin前体。α，β-二羟基烯酮的氧化环化的唯一产物是五元呋喃-3（2 H）-one衍生物，这表明这些二醇的闭环具有化学选择性和区域选择性。

  DOI：

  10.1021/jo051274d
• 作为产物：
  描述：

  triethyl 2-methyl-3-oxo-5-phenyl-2-phosphonopentanoate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以49%的产率得到ethyl (E)-2-methyl-5-phenylpent-2-enoate
  参考文献：
  名称：

  Tandem reduction–olefination for the stereoselective synthesis of (Z)-α-fluoro-α,β-unsaturated esters

  摘要：

  A tandem stereoselective reduction-olefination reaction of ethyl 2-acyl-2-fluoro-2-diethylphosphonoacetate employing NaBH4 in EtOH was developed. The one-pot reaction gave alpha-fluoro-alpha,beta-unsaturated esters with excellent (Z)-selectivity. A plausible mechanism involving a diastereoselective reduction predicted by the Felkin-Anh model, followed by olefination similar to the Horner-Wadsworth-Emmons reaction, has been proposed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00778-0

文献信息

• Recent Advances in Iridium-Catalyzed Asymmetric Hydrogenation: New Catalysts, Substrates and Applications in Total Synthesis
  作者：Adnan Ganić、Denise Rageot、Lars Tröndlin、Andreas Pfaltz

  DOI：10.2533/chimia.2012.187

  日期：——

  asymmetric hydrogenation has emerged as a highly efficient method for the synthesis of enantiomerically pure compounds. This account summarizes our recent efforts in this field. We have developed a new type of P,O-ligand that was successfully applied to the asymmetric hydrogenation of alpha,beta-unsaturated carbonyl compounds. Furthermore we have demonstrated the potential of known iridium catalysts in the

  铱催化的不对称氢化反应已成为合成对映体纯化合物的高效方法。此帐户总结了我们在该领域的最新努力。我们已经开发出一种新型的P，O-配体，已成功应用于α，β-不饱和羰基化合物的不对称加氢。此外，我们已经证明了已知的铱催化剂在α，β-不饱和硼酸酯加氢中的潜力。最后，我们可以证明铱催化的不对称氢化在天然产物Platensimycin的正式合成中的效用。
• Electrophile-Controlled Regiodivergent Palladium-Catalyzed Imidoylative Spirocyclization of Cyclic Alkenes
  作者：Shumin Ding、Yue Pu、Jiao Lin、Haixia Zhao、Qiang Tang、Jian Wang

  DOI：10.1021/acs.orglett.4c00181

  日期：2024.3.8

  spirocyclization of isocyano cycloalkenes has been developed, offering efficient and selective approaches toward spirocyclic hydropyrrole scaffolds. 2-Azaspiro-1,7-dienes could be obtained through a “chain-walking” process with aryl/vinyl iodides as electrophiles, while the normal Heck product 2-azaspiro-1,6-dienes were selectively generated when aryl triflates were used as the coupling partner of isocyanides

  开发了一种分子间可控的钯催化异氰基环烯烃螺环化反应，为螺环氢吡咯支架提供了有效且选择性的方法。 2-氮杂螺-1,7-二烯可以通过芳基/乙烯基碘作为亲电子试剂的“链行走”过程获得，而当使用芳基三氟甲磺酸酯时，可以选择性地生成正常的 Heck 产物 2-氮杂螺-1,6-二烯作为异氰化物的偶联伙伴。机理研究表明 Pd(II) 中间体的抗衡阴离子在区域选择性控制中发挥着至关重要的作用。二氢吡咯稠合的 5,6,7 元螺环在温和条件下可切换，具有广泛的官能团耐受性。
• Diastereoselective protonation of dienols: a formal approach to zaragozic acid C side chain
  作者：Sébastien Comesse、Olivier Piva

  DOI：10.1016/s0957-4166(99)00102-0

  日期：1999.3

  The 2-methyl 5-phenylpropanal precursor of the side chain of zaragozic acid C has been prepared in 83% ee through the diastereoselective protonation of a photodienol generated in situ by irradiation of an alpha, beta-unsaturated ester, bearing, as a chiral moiety, the diacetone D-glucose group. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Palladium-Catalyzed Oxidative Cyclizations:  Synthesis of Dihydropyranones and Furanones
  作者：Maud Reiter、Hazel Turner、Rebecca Mills-Webb、Véronique Gouverneur

  DOI：10.1021/jo051274d

  日期：2005.10.1

  good yields. The Pd(II)-mediated oxidative cyclization was expanded to α-hydroxyenones leading to furan-3(2H)-one derivatives, which include natural product bullatenone and a known precursor of geiparvarin. The sole product of the oxidative cyclization of α,β-dihydroxyenone was a five-membered furan-3(2H)-one derivative, suggesting that the ring closure of these diols is both chemo- and regioselective

  将引起各种β-羟基烯酮的硼介导的顺式和反式立体选择性醛醇缩合反应与Pd （II）介导的氧化环化反应偶联，以高收率得到2,3,6-三取代的顺式和反式二氢吡喃酮。Pd （II）介导的氧化环化反应扩展为α-羟基烯酮，生成了呋喃3（2 H）-one衍生物，其中包括天然产物Bullatenone和已知的geiparvarin前体。α，β-二羟基烯酮的氧化环化的唯一产物是五元呋喃-3（2 H）-one衍生物，这表明这些二醇的闭环具有化学选择性和区域选择性。
• Tandem reduction–olefination for the stereoselective synthesis of (Z)-α-fluoro-α,β-unsaturated esters
  作者：Shigeki Sano、Katsuyuki Saito、Yoshimitsu Nagao

  DOI：10.1016/s0040-4039(03)00778-0

  日期：2003.5

  A tandem stereoselective reduction-olefination reaction of ethyl 2-acyl-2-fluoro-2-diethylphosphonoacetate employing NaBH4 in EtOH was developed. The one-pot reaction gave alpha-fluoro-alpha,beta-unsaturated esters with excellent (Z)-selectivity. A plausible mechanism involving a diastereoselective reduction predicted by the Felkin-Anh model, followed by olefination similar to the Horner-Wadsworth-Emmons reaction, has been proposed. (C) 2003 Elsevier Science Ltd. All rights reserved.