4-methyl-5-[(2S,3S,4S)-4-methyl-5-oxo-3-(3-oxobutyl)-tetrahydrofuran-2-yl]-cyclopent-4-ene-1,3-dione | 1103531-14-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methyl-5-[(2S,3S,4S)-4-methyl-5-oxo-3-(3-oxobutyl)-tetrahydrofuran-2-yl]-cyclopent-4-ene-1,3-dione
• 英文别名: 1,10-dioxo-1,10-deoxy-1,10-secogorgonolide；4-methyl-5-[(2S,3S,4S)-4-methyl-5-oxo-3-(3-oxobutyl)oxolan-2-yl]cyclopent-4-ene-1,3-dione
• CAS: 1103531-14-1
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: OEIXSGHSUKFZJN-BXGCZWRVSA-N

物化性质

• 沸点：
  486.0±45.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methyl-5-[(2S,3S,4S)-4-methyl-5-oxo-3-(3-oxobutyl)-tetrahydrofuran-2-yl]-cyclopent-4-ene-1,3-dione 在 铬酸叔丁酯 、 乙酸酐 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以40%的产率得到
  参考文献：
  名称：

  Paraconic酸和1,10-的总合成开环-Guaianolides经由3-巴尔比埃烯丙基化/ Translactonization级联（溴甲基）-2（5 ħ） -呋喃酮

  摘要：

  建立了钯催化的Barbier烯丙基化/转内酯化级联反应，以快速构建倍半萜中的重要基序β，γ-二取代的α-外切-亚甲基-γ-丁内酯。二甲基锌在作为亲核体的π-烯丙基铝的增强和促进路易斯酸介导的反内酯化的两个步骤中都起着重要作用。这个序列显示广泛的底物范围和进一步利用，对于两个paraconic酸的合成方法以及两个1,10-第一保护-自由基的全合成开环-guaianolides。

  DOI：

  10.1021/acs.orglett.0c04165
• 作为产物：
  描述：

  山道年 在 硫酸 、 水 、 臭氧 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 56.0h， 生成 4-methyl-5-[(2S,3S,4S)-4-methyl-5-oxo-3-(3-oxobutyl)-tetrahydrofuran-2-yl]-cyclopent-4-ene-1,3-dione
  参考文献：
  名称：

  Facile Preparation of Bioactiveseco-Guaianolides and Guaianolides fromArtemisia gorgonumand Evaluation of Their Phytotoxicity

  摘要：

  Commercially available santonin was used to synthesize seven sesquiterpene lactones using a fade strategy that involved a high-yielding photochemical reaction. Three natural products from Artemisia gorgonum were synthesized in good yields, and in the case of two compounds, absolute configurations were determined from X-ray quality crystals. The structures previously reported for these compounds were revised. Sesquiterpene lactones were tested using the etiolated wheat coleoptile bioassay, and the most active compounds were assayed in standard target species, seco-Guaianolide (4) showed higher phytotoxic activities than the known herbicide Logran. This high activity could be due to the presence of a cyclopentenedione ring. These results suggest that compound 4 should be involved in defense of A. gorgorum, displaying a wide range of activities that allow proposing them as new leads for development of a natural herbicide model with a seco-guaianolide skeleton.

  DOI：

  10.1021/np300639b

文献信息

• Total Syntheses of Paraconic Acids and 1,10-<i>seco</i>-Guaianolides via a Barbier Allylation/Translactonization Cascade of 3-(Bromomethyl)-2(5<i>H</i>)-furanone
  作者：Weilong Liu、Zhimei Yu、Nicolas Winssinger

  DOI：10.1021/acs.orglett.0c04165

  日期：2021.2.5

  palladium-catalyzed Barbier allylation/translactonization cascade reaction was established for the rapid construction of β,γ-disubstituted α-exo-methylene-γ-butyrolactone, an important motif in sesquiterpenes. Dimethyl zinc played significant roles in both steps for the umpolung of π-allylpalladium as a nucleophile and promoting a Lewis acid-mediated translactonization. This sequence showed a broad substrate

  建立了钯催化的Barbier烯丙基化/转内酯化级联反应，以快速构建倍半萜中的重要基序β，γ-二取代的α-外切-亚甲基-γ-丁内酯。二甲基锌在作为亲核体的π-烯丙基铝的增强和促进路易斯酸介导的反内酯化的两个步骤中都起着重要作用。这个序列显示广泛的底物范围和进一步利用，对于两个paraconic酸的合成方法以及两个1,10-第一保护-自由基的全合成开环-guaianolides。
• Facile Preparation of Bioactive<i>seco</i>-Guaianolides and Guaianolides from<i>Artemisia gorgonum</i>and Evaluation of Their Phytotoxicity
  作者：Francisco A. Macías、Alejandro Santana、Azusa Yamahata、Rosa M. Varela、Frank R. Fronczek、José M. G. Molinillo

  DOI：10.1021/np300639b

  日期：2012.11.26

  Commercially available santonin was used to synthesize seven sesquiterpene lactones using a fade strategy that involved a high-yielding photochemical reaction. Three natural products from Artemisia gorgonum were synthesized in good yields, and in the case of two compounds, absolute configurations were determined from X-ray quality crystals. The structures previously reported for these compounds were revised. Sesquiterpene lactones were tested using the etiolated wheat coleoptile bioassay, and the most active compounds were assayed in standard target species, seco-Guaianolide (4) showed higher phytotoxic activities than the known herbicide Logran. This high activity could be due to the presence of a cyclopentenedione ring. These results suggest that compound 4 should be involved in defense of A. gorgorum, displaying a wide range of activities that allow proposing them as new leads for development of a natural herbicide model with a seco-guaianolide skeleton.