1,1-二乙酰基-2-(6-甲基-4-氧代-4H-1-苯并吡喃-3-基)乙烯 | 112635-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 1,1-二乙酰基-2-(6-甲基-4-氧代-4H-1-苯并吡喃-3-基)乙烯
• 英文名称: 1,1-Diacetyl-2-(6-methyl-4-oxo-4H-1-benzopyran-3-yl)ethylene
• 英文别名: 3-[(6-methyl-4-oxo-4H-1-benzopyran-3-yl)methylene]pentan-2,4-dione；3-((6-methyl-4-oxo-4H-chromen-3-yl)methylene)pentane-2,4-dione；3-[(6-Methyl-4-oxochromen-3-yl)methylidene]pentane-2,4-dione
• CAS: 112635-27-5
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: BUEYSKGCTOWQMG-UHFFFAOYSA-N

物化性质

• 沸点：
  442.3±45.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-二乙酰基-2-(6-甲基-4-氧代-4H-1-苯并吡喃-3-基)乙烯 在 ammonium chloride 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以40%的产率得到3-((6-methyl-4-oxo-4H-chromen-3-yl)methyl)pentane-2,4-dione
  参考文献：
  名称：

  Chemoselective Reduction of Some Condensates derived from Chromone-3-carbaldehyde using Sm and Zn

  摘要：

  Condensates 4-6 undergo reductive dimerization with Sm in THF containing aqueous NH4Cl to produce 7-9, whereas with Zn under similar reaction condition 3-5 produce 10-12.

  DOI：

  10.1080/00397910802139049
• 作为产物：
  描述：

  6-甲基-4-氧-4H-1-苯并吡喃-3-甲醛 、 乙酰丙酮 在 乙酸酐 、 potassium carbonate 作用下， 反应 0.67h， 以75%的产率得到1,1-二乙酰基-2-(6-甲基-4-氧代-4H-1-苯并吡喃-3-基)乙烯
  参考文献：
  名称：

  Metal-Free Cascade Approach toward Polysubstituted Indolizines from Chromone-Based Michael Acceptors

  摘要：

  An efficient cascade transformation toward indolizine-based molecules has been developed. This process leads to the rapid construction of two C-N bonds and one C-C bond without the need of any metal catalysis. The approach involves easily accessible chromone-based Michael acceptors and propargylamine derivatives as starting materials. This cascade constitutes a novel and very competitive alternative to the well reported strategies using pyridine or pyrrole derivatives for accessing the indolizine ring with substituents at uncommon C-positions

  DOI：

  10.1021/acs.orglett.7b00309

文献信息

• Reactions of 4-Oxo-4H-1-benzopyran-3-carboxaldehydes with Pentane-2,4-dione in Acidic Medium—a New Route to Dihydroxybenzophenone Derivatives
  作者：Chandrakanta Bandyopadhyay、Kumar Ranabir Sur、Ranjan Patra

  DOI：10.1039/a804173c

  日期：——

  Reaction of the title aldehyde 1 with acetylacetone 2 gives benzophenone 8 along with the Knoevenagel-type product 5 under acidic conditions.

  在酸性条件下，标题醛 1 与乙酰丙酮 2 反应得到二苯甲酮 8 和 Knoevenagel 型产物 5。
• A Mild and Efficient Route to 3-Vinylchromones in Aqueous Micellar Media
  作者：Vikash Kumar、Amrita Chatterjee、Mainak Banerjee

  DOI：10.1080/00397911.2015.1084008

  日期：2015.10.18

  A simple, mild, and ecofriendly method has been developed for the synthesis of 3-vinylchromones from 4-oxo-4H-1-benzopyran-3-carboxaldehyde (3-formylchromone) by simple Knoevenagel condensation with various active methylene compounds (AMC) in aqueous micellar media in the presence of catalytic amounts of cetyl trimethylammonium bromide (CTAB) and 1,4-diazabicyclo[2.2.2]octane (DABCO). In the case of malonic acid as AMC, the reaction resulted in formation of only Doebner decarboxylated products under the standard reaction condition. It has been also observed that 3-formylchromone derivatives primarily undergo tandem Knoevenagel and Michael reactions in the presence of >2 equiv. of ethyl acetoacetate to produce benzophenone derivatives, by opening of pyran ring, as the sole product in good yields.
• Bandyopadhyay, Chandrakanta; Nag, Partha Pratim; Sur, Kumar Ranabir, Journal of the Indian Chemical Society, 2004, vol. 81, # 2, p. 132 - 136
  作者：Bandyopadhyay, Chandrakanta、Nag, Partha Pratim、Sur, Kumar Ranabir、Patra, Ranjan、Banerjee, Subhabrata、Sen, Arunabha、Ghosh, Tapas

  DOI：——

  日期：——
• Ghosh, Chandra Kanta; Sahana, Sirin; Bandyopadhyay, Chandrakanta, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 6, p. 624 - 629
  作者：Ghosh, Chandra Kanta、Sahana, Sirin、Bandyopadhyay, Chandrakanta

  DOI：——

  日期：——
• Ghosh, Chandra Kanta; Bhattacharyya, Atanu; Ghosh-Dastidar, Partha Pratim, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 423 - 426
  作者：Ghosh, Chandra Kanta、Bhattacharyya, Atanu、Ghosh-Dastidar, Partha Pratim

  DOI：——

  日期：——