(E)-4-(2,5-dimethoxyphenyl)-3-butenoic acid | 83655-42-9

• 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: (E)-4-(2,5-dimethoxyphenyl)-3-butenoic acid
• 英文别名: (E)-4-(2,5-dimethoxyphenyl)but-3-enoic acid；4-(2,5-Dimethoxy-phenyl)-but-3-enoic acid
• CAS: 83655-42-9
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: LWOKRIASKVODMR-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-(2,5-dimethoxyphenyl)-3-butenoic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 methyl (E)-4-(2',5'-dimethoxyphenyl)but-3-enoate
  参考文献：
  名称：

  通过芳基二氧杂环戊基乙酸酯的重排合成异铬烷-3-基乙酸酯和异铬烷-γ-内酯

  摘要：

  路易斯酸催化甲基4,5-反式重排-4-芳基二氧杂戊基-5-基乙酸酯1为取代的甲基异色满-3-基乙酸酯2和异铬烷-γ-内酯3提供了便利的途径。路易斯酸的选择取决于芳环的取代方式。从母体二氧戊环不变地转移了两个连续的异铬烷立体中心，而异铬烷甲基的构型取决于芳基取代，试剂和反应条件。因此，用樟脑磺酸处理C-2表异构体3'，5'-二甲氧基苯基二氧戊环4和5提供了C-5表异构体异苯并二氢吡喃内酯26和29的混合物，前者在较低的酸浓度下是有利的，后者在较高的酸浓度下是有利的。 。四氯化钛将类似的2'-氯-5'-甲氧基苯基二氧戊环酮6和7异构化为异色满-3-基乙酸乙酸甲酯38，可将其内酯化为异色烷内酯27。磷酸将2'，5'-二甲氧基苯基二氧戊环酮8和在异丁烷内酯28和31的混合物中加入图9所示的化合物，同时在乙醛存在下对羟基内酯22进行类似处理，直接并完全非对映选择性地得到异苯二甲基内酯28。该异色烷内酯28的氧化脱甲基和环化反应提供了5-

  DOI：

  10.1039/a807005i
• 作为产物：
  描述：

  巴豆酸 、 1-溴-2,5-二甲氧基苯 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 生成 (E)-4-(2,5-dimethoxyphenyl)-3-butenoic acid
  参考文献：
  名称：

  Reaction of 2-butenoic acid dianion and its N-(4-methoxyphenyl)amide with methoxy-substituted arynes

  摘要：

  N-(4-Methoxyphenyl)-1-butenamide dianion (6), generated by the reaction of N-(4-methoxyphenyl)-2-butenamide (3) with LDA or LTMP, undergoes exclusive 4-arylation with various methoxy-substituted arynes 2a-e yielding mixtures consisting of a N-(4-methoxyphenyl)-(E)-4-aryl-3-butenamide 9 (85-90%) and a N-(4-methoxyphenyl)-(E)-4-aryl-2-butenamide 9' (10-15%). Under certain conditions, 4,4-diarylated products 12 are also obtained. 2-Butenoic acid dianion (14) also reacts with methoxy-substituted arynes affording predominantly 4-aryl-3-butenoic acids 15 and minor amounts of 4-aryl-2-butenoic acids 15'. The exclusive low temperature (-30 to -40-degrees-C) 4-addition of arynes to dianion 14 is in contrast to the predominant 2-addition that 14 undergoes with certain aldehydes and ketones at comparable temperatures. The mixtures of 4-arylbutenoic acids 15 and 15' and 4-arylbutenamides 9 and 9' were readily hydrogenated (Pd/C) and esterified (MeOH/H2SO4) to synthetically valuable methyl 4-arylbutanoates 17.

  DOI：

  10.1021/jo00028a049

文献信息

• Cobalt-Catalyzed Allylic C(sp³)–H Carboxylation with CO₂
  作者：Kenichi Michigami、Tsuyoshi Mita、Yoshihiro Sato

  DOI：10.1021/jacs.7b02775

  日期：2017.5.3

  tolerability, so that selective addition to CO2 occurred in the presence of other carbonyl groups such as amide, ester, and ketone. Since styrylacetic acid derivatives can be readily converted into optically active γ-butyrolactones through Sharpless asymmetric dihydroxylation, this allylic C(sp3)-H carboxylation showcases a facile synthesis of γ-butyrolactones from simple allylarenes via short steps.

  借助 Co/Xantphos 复合物开发了末端烯烃的烯丙基 C(sp3)-H 键与 CO2 的催化羧化。广泛的烯丙基芳烃和 1,4-二烯以中等至高产率成功转化为线性苯乙烯乙酸和六-3,5-二烯酸衍生物，并具有出色的区域选择性。羧化显示出显着的官能团耐受性，因此在其他羰基（如酰胺、酯和酮）存在的情况下，会发生选择性加成到 CO2 中。由于苯乙烯乙酸衍生物可以通过 Sharpless 不对称二羟基化很容易地转化为光学活性的 γ-丁内酯，这种烯丙基 C(sp3)-H 羧化展示了从简单的烯丙基芳烃通过短步骤轻松合成 γ-丁内酯。
• Direct Enantioselective and Regioselective Alkylation of β,γ-Unsaturated Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries
  作者：Kai Yu、Bukeyan Miao、Wenqi Wang、Armen Zakarian

  DOI：10.1021/acs.orglett.9b00587

  日期：2019.3.15

  Efficient asymmetric alkylation of β,γ-unsaturated carboxylic acids without prior functionalization is enabled by chiral lithium amides. Enantioselectivity is imparted by a putative mixed lithium amide–enediolate aggregate that acts a traceless auxiliary formed in situ, allowing for a direct asymmetric alkylation and a simple recovery of the chiral reagent.

  β，γ-不饱和羧酸的有效不对称烷基化无需事先官能化就可以通过手性锂酰胺实现。对映选择性是由假定的酰胺基-烯二醇锂混合聚集体赋予的，该聚集体发挥就地形成的无痕助剂的作用，允许直接不对称烷基化和简单回收手性试剂。
• Reaction of 2-butenoic acid dianion and its N-(4-methoxyphenyl)amide with methoxy-substituted arynes
  作者：Abdul Rakeeb Deshmukh、Tran Long、Edward R. Biehl

  DOI：10.1021/jo00028a049

  日期：1992.1

  N-(4-Methoxyphenyl)-1-butenamide dianion (6), generated by the reaction of N-(4-methoxyphenyl)-2-butenamide (3) with LDA or LTMP, undergoes exclusive 4-arylation with various methoxy-substituted arynes 2a-e yielding mixtures consisting of a N-(4-methoxyphenyl)-(E)-4-aryl-3-butenamide 9 (85-90%) and a N-(4-methoxyphenyl)-(E)-4-aryl-2-butenamide 9' (10-15%). Under certain conditions, 4,4-diarylated products 12 are also obtained. 2-Butenoic acid dianion (14) also reacts with methoxy-substituted arynes affording predominantly 4-aryl-3-butenoic acids 15 and minor amounts of 4-aryl-2-butenoic acids 15'. The exclusive low temperature (-30 to -40-degrees-C) 4-addition of arynes to dianion 14 is in contrast to the predominant 2-addition that 14 undergoes with certain aldehydes and ketones at comparable temperatures. The mixtures of 4-arylbutenoic acids 15 and 15' and 4-arylbutenamides 9 and 9' were readily hydrogenated (Pd/C) and esterified (MeOH/H2SO4) to synthetically valuable methyl 4-arylbutanoates 17.
• Synthesis of isochroman-3-ylacetates and isochromane-γ-lactones through rearrangement of aryldioxolanylacetates
  作者：Robin G. F. Giles、Rodney W. Rickards、Badra S. Senanayake

  DOI：10.1039/a807005i

  日期：——

  Lewis acid catalysed rearrangement of methyl 4,5-trans-4-aryldioxolan-5-ylacetates 1 provides a convenient route to substituted methyl isochroman-3-ylacetates 2 and isochromane-γ-lactones 3. The choice of Lewis acid is determined by the substitution pattern of the aromatic ring. The two contiguous isochromane stereocentres are transferred unchanged from the parent dioxolanes, while the configuration

  路易斯酸催化甲基4,5-反式重排-4-芳基二氧杂戊基-5-基乙酸酯1为取代的甲基异色满-3-基乙酸酯2和异铬烷-γ-内酯3提供了便利的途径。路易斯酸的选择取决于芳环的取代方式。从母体二氧戊环不变地转移了两个连续的异铬烷立体中心，而异铬烷甲基的构型取决于芳基取代，试剂和反应条件。因此，用樟脑磺酸处理C-2表异构体3'，5'-二甲氧基苯基二氧戊环4和5提供了C-5表异构体异苯并二氢吡喃内酯26和29的混合物，前者在较低的酸浓度下是有利的，后者在较高的酸浓度下是有利的。 。四氯化钛将类似的2'-氯-5'-甲氧基苯基二氧戊环酮6和7异构化为异色满-3-基乙酸乙酸甲酯38，可将其内酯化为异色烷内酯27。磷酸将2'，5'-二甲氧基苯基二氧戊环酮8和在异丁烷内酯28和31的混合物中加入图9所示的化合物，同时在乙醛存在下对羟基内酯22进行类似处理，直接并完全非对映选择性地得到异苯二甲基内酯28。该异色烷内酯28的氧化脱甲基和环化反应提供了5-