Methyl-(E)-2-methyl-4-phenyl-2-buteonate | 79265-44-4

• 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: Methyl-(E)-2-methyl-4-phenyl-2-buteonate
• 英文别名: methyl (E)-2-methyl-4-phenylbut-2-enoate
• CAS: 79265-44-4
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: ITWAVSQDSMBKQQ-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  Methyl-(E)-2-methyl-4-phenyl-2-buteonate 在 lithium hydroxide 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 30.0h， 生成 3-benzyl-2-methyl-2-oxiranecarboxylic acid
  参考文献：
  名称：

  Stereoselectivity Control in Reactions of Tertiary 2-Oxacycloalkyl Radicals

  摘要：

  我们研究了由 1,3-二氧戊环-4-基和环氧乙烷环自由基介导的反应的立体化学结果。在自由基中心旁边存在一个非常笨重的取代基具有显著的同步引导作用。这些立体选择性通过一个模型得到了合理解释，该模型考虑到了自由基的金字塔化、连接到循环上的取代基之间的立体相互作用以及与进入的自由基陷阱之间的立体相互作用。

  DOI：

  10.1055/s-1997-1346
• 作为产物：
  描述：

  2-Methyl-4-phenyl-3-tosylbutanoic acid 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl-(E)-2-methyl-4-phenyl-2-buteonate
  参考文献：
  名称：

  Lithium 3-Lithio-3-tosylalkanoates: .beta.-Acylvinyl Anion Equivalents of .beta.-Lithiated .alpha.,.beta.-Unsaturated Carboxylic Acids

  摘要：

  The dilithiation of beta-tosylated propanoic, 2-methylpropanoic, and butanoic acid 10 with n-butyllithium at -78 degrees C leads to the corresponding lithium 3-lithio-3-tosylalkanoates 11. They react with different electrophilic reagents (deuterium oxide, iodine, trimethylchlorosilane, alkyl halides, and acyl chlorides) to give the corresponding 3-substituted tosylated alkanoic acids 12. When carbonyl compounds are allowed to react with intermediates 11 followed by in situ lactonization with trifluoracetic anhydride and base-promoted elimination alpha,beta-butenolides are obtained. This methodology is applied to the direct synthesis of the rosefuran lactone precursor 14cg, the O-benzyl derivative of (+/-)-umbelactone (14ch), and (+/-)-andirolactone (14ci). The alkylation and acylation reactions of organolithium compounds 11 followed by esterification with hydrogen chloride in methanol and treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afford alpha,beta- and/or beta,gamma-unsaturated esters 17 and/or 18 and unsaturated 4-keto esters 19, respectively. The last methodology has been applied to the synthesis of the unsaturated 4-keto ester 19ae precursor of the seco acid of (+/-)-pyrenophorin (22).

  DOI：

  10.1021/jo00090a043

文献信息

• Control of Regioselectivity by the <i>l</i><i>one</i> Substituent through Steric and Electronic Effects in the Nitrosoarene Ene Reaction of Deuterium-Labeled Trisubstituted Alkenes
  作者：Waldemar Adam、Oliver Krebs、Michael Orfanopoulos、Manolis Stratakis

  DOI：10.1021/jo026198i

  日期：2002.11.1

  For the ene reaction of 4-nitronitrosobenzene (ArNO) with a variety of primary and secondary lone alkyl-substituted substrates, the twix/twin regioselectivity is constant at about 85:15. In contrast, for the lone tert-butyl group and for lone aryl substituents, the twix regioisomer is obtained exclusively. These regioselectivities have been rationalized in terms of steric interactions and coordination

  对于4-硝基亚硝基苯（ArNO）与多种伯和仲孤烷基取代的底物的烯反应，twix / twin区域选择性恒定在约85:15。相反，对于单独的叔丁基和对于单独的芳基取代基，仅获得twix区域异构体。这些区域选择性已经在第一步反应的过渡态中，在亲和体与底物之间的空间相互作用和配位方面得到了合理化。
• Highly selective synthesis of allylated arenes and diarylmethanes via palladium-catalyzed cross coupling involving benzylic derivatives
  作者：Ei-ichi Negishi、Hajime Matsushita、Nobuhisa Okukado

  DOI：10.1016/s0040-4039(01)90533-7

  日期：1981.1

  The Pd-catalyzed cross coupling of either benzylzincs with alkenyl halides or alkenylalanes with benzyl halides provides highly selective and expeditious routes to allylated arenes.

  苄基锌与链烯基卤化物或链烯基丙二烯与苄基卤化物的Pd催化交叉偶合为烯丙基化芳烃提供了高度选择性和快速的途径。
• Site Specificity in the Photooxidation of Some Trisubstituted Alkenes in Thionin-Supported Zeolite Na−Y. On the Role of the Alkali Metal Cation
  作者：Manolis Stratakis、George Froudakis

  DOI：10.1021/ol000021y

  日期：2000.5.1

  The less substituted side of some geminal dimethyl trisubstituted alkenes becomes significantly more reactive if photooxygenation takes place in thionin-supported zeolite Na-Y. These results are mainly attributed to a synergistic interaction between the alkali metal cation, the alkene, and the oxygen in the transition state of perepoxide formation.

  如果在硫黄素负载的沸石Na-Y中发生光氧合，则某些双键二甲基三取代的烯烃的较少取代的一侧会变得更具活性。这些结果主要归因于碱金属阳离子，烯烃和氧在过氧化物形成过渡态中的协同相互作用。
• Compositions and methods for visible-light-controlled ruthenium-catalyzed olefin metathesis
  申请人：The Trustees of Columbia University In The City of New York

  公开号：US11331656B2

  公开（公告）日：2022-05-17

  The present disclosure provides compositions and methods for metathesizing a first alkenyl or alkynyl group with a second alkenyl or alkynyl group, the composition comprising a ruthenium metathesis catalyst and a photoredox catalyst that is activated by visible light.

  本公开提供了将第一烯基或炔基与第二烯基或炔基进行偏析的组合物和方法，该组合物包括钌偏析催化剂和由可见光激活的光氧化催化剂。
• Arylation and Vinylation of α-Diazocarbonyl Compounds with Boroxines
  作者：Cheng Peng、Wei Zhang、Guobing Yan、Jianbo Wang

  DOI：10.1021/ol900362d

  日期：2009.4.2

  An alternative approach for alpha-arylation and alpha-vinylation of carbonyl compounds is described: reaction between aryl- or vinylboroxines with alpha-diazocarbonyl compounds leads to the formation of alpha-arylated or alpha-vinylated carbonyl compounds under mild conditions.