ethyl 3-methyl-4-phenylbut-2-enoate | 75321-72-1

• 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: ethyl 3-methyl-4-phenylbut-2-enoate
• CAS: 75321-72-1
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: QLWHNDGMFGORBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  89-91 °C(Press: 0.5 Torr)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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 3-methyl-4-phenylbut-2-enoate 在 sodium hydroxide 、 乙醚 作用下， 生成 methyl (E)-3-methyl-4-phenylbut-3-enoate
  参考文献：
  名称：

  Canonica et al., Farmaco, Edizione Scientifica, 1959, vol. 14, p. 122,132

  摘要：

  DOI：
• 作为产物：
  描述：

  3-羟基-3-甲基-4-苯基丁酸乙酯 生成 ethyl 3-methyl-4-phenylbut-2-enoate
  参考文献：
  名称：

  Synthesis of the Six Carboxybenzo[c]phenanthrenes^1,2

  摘要：

  DOI：

  10.1021/jo01065a015

文献信息

• Development of general methods for the synthesis of new substituted allyl bromides as promising alkenylating agents
  作者：A. I. Moskalenko、V. I. Boev

  DOI：10.1134/s1070428014070069

  日期：2014.7

  A general procedure has been developed for the synthesis of hitherto unknown substituted allyl bromides. The procedure includes preparation of the corresponding α,β-unsaturated carboxylic acid esters from accessible ketones according to the Horner-Emmons reaction, reduction of these esters with diisobutylaluminum hydride to allylic alcohols, and substitution of the hydroxy group by bromine by the action

  已经开发了用于合成迄今未知的取代的烯丙基溴的通用方法。该方法包括根据霍纳-埃蒙斯反应，从易得的酮中制备相应的α，β-不饱和羧酸酯，将其用氢化二异丁基铝还原为烯丙基醇，并通过PBr的作用将溴取代成羟基3。合成的不饱和化合物的E，Z异构体比例为3：1至4：1。
• Titanium(IV) Chloride-Mediated Stereoselective α-Alkylidenation to Efficiently Assemble Multisubstituted 1,3-Dienes
  作者：Rengwei Sun、Wei Song、Chunmei Ma、Huiwen Zhang、Xinhong Yu

  DOI：10.1002/adsc.201601025

  日期：2016.12.22

  multisubstituted 1,3‐dienes by α‐exclusive alkylidenation of crotonic derivatives has been developed. This protocol, mediated by titanium tetrachloride chelation, features excellent regio‐ and stereoselectivity, mild reaction conditions, easy operation and wide substrate scope. Conversions of the derived dienes to other useful molecules were also explored.

  已经开发了通过巴豆​​衍生物的α排他性烷基化直接获得多取代的1,3二烯的方法。该方案由四氯化钛螯合介导，具有出色的区域和立体选择性，温和的反应条件，易于操作和广泛的底物范围。还研究了衍生的二烯向其他有用分子的转化。
• Thioepoxide formation by ring closure of allylthiyl radicals—a novel rearrangement of allylic thionitrites
  作者：Marta Cavero、William B. Motherwell、Pierre Potier、Jean-Marc Weibel

  DOI：10.1039/b207252c

  日期：——

  Tertiary allylic thionitrites undergo thermal rearrangement to alpha,beta-episulfide nitroso dimers via ring closure of allylthiyl radicals.

  叔烯丙基硫代亚硝酸盐通过烯丙基硫基自由基的闭环进行热重排成α，β-环二硫亚硝基二聚体。
• TMSCl-Mediated Catalytic Carbocupration of Alkynoates: An Unprecedented and Remarkable Effect of Catalyst Loading on Highly Selective Stereochemical Induction via a TMS-Allenoate Intermediate
  作者：Michael P. Jennings、Kailas B. Sawant

  DOI：10.1002/ejoc.200400314

  日期：2004.8

  The TMSCl-mediated catalytic carbocupration of alkynoates has been investigated. It has been shown that catalyst loadings as low as 30 mol% readily allow for high yields and diastereoselectivities for a series of Grignard reagents. In addition, an unprecedented and remarkable effect of catalyst loading on stereochemical induction has been observed. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  已经研究了 TMSCl 介导的炔酸酯催化碳化。已经表明，低至 30 mol% 的催化剂负载量很容易实现一系列格氏试剂的高产率和非对映选择性。此外，还观察到催化剂负载对立体化学诱导的前所未有的显着影响。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Rearrangement Reactions Leading to Optically Active α,α-Disubstituted Primary Allylamines
  作者：Martin Hennum、Hege Hortemo Odden、Lise-Lotte Gundersen

  DOI：10.1002/ejoc.201601446

  日期：2017.1.26

  Synthetic routes to α,α-disubstituted allylamines have been examined. Racemic compounds were conveniently prepared by thermal Overman rearrangements of primary allyl alcohols with trisubstituted double bonds, but rearrangement of these substrates by the only commercially available compound known to catalyze enantioselective Overman rearrangements, the cobalt oxazoline palladacycle (R)-COP-Cl, failed

  已经研究了 α,α-二取代烯丙胺的合成路线。外消旋化合物可通过具有三取代双键的伯烯丙醇的热 Overman 重排方便地制备，但通过已知可催化对映选择性 Overman 重排的唯一市售化合物，钴恶唑啉钯环 (R)-COP-Cl 对这些底物进行重排失败。相反，通过 CBS 介导的相应甲基酮还原获得的具有三取代双键的光学活性仲烯丙醇被合成并通过热 Overman 重排或烯丙酯到异氰酸酯重排转化为 α,α-二取代烯丙胺。两个反应序列都获得了高手性转移 (90-99%)，