α,γ-Dimethyl-γ-phenyl-allencarbonsaeure | 36858-88-5

• 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: α,γ-Dimethyl-γ-phenyl-allencarbonsaeure
• 英文别名: racem.-2-Methyl-4-phenyl-pentadien-(2,3)-carbonsaeure；racem. 2-Methyl-4-phenyl-2,3-pentadiensaeure；2-methyl-4-phenylpenta-2,3-dienoic acid
• CAS: 36858-88-5
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: ULJBJOQSKVNZTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  α,γ-Dimethyl-γ-phenyl-allencarbonsaeure 在 Selectfluor 作用下， 以 水 、 乙腈 为溶剂， 反应 10.0h， 以81%的产率得到4-fluoro-3,5-dimethyl-5-phenyl-2(5H)-furanone
  参考文献：
  名称：

  An Efficient Approach for Monofluorination via Aqueous Fluorolactonization Reaction of 2,3-Allenoic Acids with Selectfluor

  摘要：

  [GRAPHICS]We have developed a convenient method for the efficient monofluorination via the electrophilic fluorocyclization reaction of 2,3-allenoic acids with Selectfluor in MeCN in the presence of 10 equiv of H2O or even in pure water to afford beta-fluorobutenolides in moderate to high yields.

  DOI：

  10.1021/jo702409y
• 作为产物：
  描述：

  2-methyl-2-phenylmalonic acid 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 α,γ-Dimethyl-γ-phenyl-allencarbonsaeure
  参考文献：
  名称：

  Kresze,G. et al., Justus Liebigs Annalen der Chemie, 1972, vol. 756, p. 112 - 127

  摘要：

  DOI：

文献信息

• Copper-Catalyzed Sulfenylation, Sulfonylation, and Selenylation of 2,3-Allenoic Acids with Disulfides or Diselenides
  作者：Ya-Xun Xin、Shen Pan、Yangen Huang、Xiu-Hua Xu、Feng-Ling Qing

  DOI：10.1021/acs.joc.8b00858

  日期：2018.6.1

  The efficient copper-catalyzed sulfenylation and selenylation of 2,3-allenoic acids with disulfides or diselenides were developed, respectively. These reactions proceeded through tandem radical addition/intramolecular cyclization processes, affording a series of 4-sulfenylated and 4-selenylated butenolides in moderate to excellent yields. Moreover, 4-sulfonylated butenolides could also be obtained

  分别开发了有效的铜催化的二硫化物或二硒化物的2,3-烯丙基酸的亚磺酰基化和硒基化反应。这些反应通过串联自由基加成/分子内环化过程进行，以中等至优异的产率提供了一系列的4-亚磺酰基化和4-硒化的丁烯内酯。此外，还可以通过2，3-烯丙酸的亚磺酰基化和随后的氧化来获得4-磺酰化的丁烯内酯。含硫和硒的丁烯内酯的进一步转化以良好的产率提供了相应的呋喃衍生物。
• Copper-Assisted Oxidative Trifluoromethylthiolation of 2,3-Allenoic Acids with AgSCF₃
  作者：Shen Pan、Yangen Huang、Xiu-Hua Xu、Feng-Ling Qing

  DOI：10.1021/acs.orglett.7b02249

  日期：2017.9.1

  3-allenoic acids with AgSCF3 in the presence of (NH4)2S2O8 and catalytic copper salt was investigated. A series of 4-aryl-2,3-allenoic acids underwent radical trifluoromethylthiolation/intramolecular cyclization to afford β-trifluoromethylthiolated butenolides, which were conveniently transformed into trifluoromethylthiolated furan derivatives. In contrast, 2-monosubstituted 2,3-allenoic acids were converted

  研究了在（NH 4）2 S 2 O 8和催化铜盐存在下，AgSCF 3对2,3-烯丙基酸的氧化三氟甲基硫醇化反应。一系列的4-芳基-2,3-烯丙酸经过自由基三氟甲基硫醇化/分子内环化反应，得到β-三氟甲基硫醇化的丁烯化物，将其方便地转化为三氟甲基硫醇化的呋喃衍生物。相反，在相似的反应条件下，将2-单取代的2，3-烯丙酸转化成相应的3，4-双（三氟甲硫基）丁-2-烯酸。
• Iron‐Catalyzed Three‐Component Cyanoalkylsulfonylation of 2,3‐Allenoic Acids, Sulfur Dioxide, and Cycloketone Oxime Esters: Access to Cyanoalkylsulfonylated Butenolides
  作者：Xiangyun Zheng、Tianshuo Zhong、Xiao Yi、Qitao Shen、Chuanliu Yin、Lei Zhang、Jian Zhou、Junyu Chen、Chuanming Yu

  DOI：10.1002/adsc.202100463

  日期：2021.7

  An iron-catalyzed three-component cyanoalkylsulfonylation of 2,3-allenoic acids, K2S2O5, and the ring-opening of cyclobutanone oxime esters is described. The radical tandem cyclization route allows access to diverse cyanoalkylsulfonylated butenolides in moderate to good yields under mild conditions. Moreover, the products are further converted, offering the corresponding derivatives.

  描述了铁催化的 2,3-丙二烯酸、K 2 S 2 O 5 的三组分氰基烷基磺酰化和环丁酮肟酯的开环。自由基串联环化路线允许在温和条件下以中等至良好的产率获得各种氰基烷基磺酰化丁烯内酯。此外，产品进一步转换，提供相应的衍生产品。
• Copper-Catalyzed Phosphorylation of 2,3-Allenoic Acids and Phosphine Oxide: Access to Phosphorylated Butenolides
  作者：Tianshuo Zhong、Xiangyun Zheng、Chuanliu Yin、Qitao Shen、Chuanming Yu

  DOI：10.1021/acs.joc.1c00998

  日期：2021.7.16

  Cu-catalyzed annulation of 2,3-allenoic acids with diphenylphosphine oxide, leading to the formation of 4-phosphate butenolides in up to 88% yield. The formation of the C–P bond provides new avenues for the functionalization of different furan-2(5H)-ones, with favorable features such as suitable functional group tolerance and mild synthesis conditions.

  我们研究了一种新型的 Cu 催化的 2,3-烯丙酸与二苯基氧化膦的环化，导致以高达 88% 的产率形成 4-磷酸丁烯内酯。C-P键的形成为不同呋喃-2( 5H )-酮的功能化提供了新的途径，具有合适的官能团耐受性和温和的合成条件等有利特征。
• Runge,W. et al., Justus Liebigs Annalen der Chemie, 1975, p. 1361 - 1378
  作者：Runge,W. et al.

  DOI：——

  日期：——