Dimethyl (2-allyloxyphenyl)methylenemalonate | 99558-32-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Dimethyl (2-allyloxyphenyl)methylenemalonate
• 英文别名: Dimethyl 2-[(2-prop-2-enoxyphenyl)methylidene]propanedioate
• CAS: 99558-32-4
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: ULXGJDUJRGCHSV-UHFFFAOYSA-N

物化性质

• 沸点：
  359.3±32.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Dimethyl (2-allyloxyphenyl)methylenemalonate 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 以32%的产率得到dimethyl 2-vinylchromane-3,3-dicarboxylate
  参考文献：
  名称：

  C−H Bond Functionalization via Hydride Transfer: Synthesis of Dihydrobenzopyrans from ortho-Vinylaryl Akyl Ethers

  摘要：

  The hydride transfer initiated cyclization ("HT-cyclization") of aryl alkyl ethers, which leads to direct coupling of sp(3) C-H bonds and activated alkenes, is reported. Readily available salicylaldehyde derived ethers are converted in one step to dihydrobenzopyrans, an important class of heteroarenes frequently found in biologically active compounds. This process has not been previously reported, in contrast to known HT-cyclizations of the corresponding tert-amines ("tert-amino effect" reactions).

  DOI：

  10.1021/ol900915p
• 作为产物：
  描述：

  Triphenylphosphonio-dicarbomethoxymethanol 在 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Dimethyl (2-allyloxyphenyl)methylenemalonate
  参考文献：
  名称：

  Carboxylic esters radical leaving groups: a new and efficient gas-phase synthesis of benzofurans

  摘要：

  邻烯丙基肉桂酸酯的闪速真空热解（FVP）可通过苯氧自由基的环化和随后的羧基酯功能裂解，得到高产率的苯并呋喃；相应苯酚的 FVP 可得到香豆素。

  DOI：

  10.1039/c39930000959

文献信息

• SUBSTITUTED CHROMANES, ANALOGS THEREOF, AND METHODS OF USE AND SYNTHESIS
  申请人：NORTHWESTERN UNIVERSITY

  公开号：US20210009547A1

  公开（公告）日：2021-01-14

  Disclosed are chromane compounds, analogs thereof, and methods of their synthesis and use. The compounds may be synthesized by methods involving reductive annulations of arylidene malonates with unsaturated electrophiles using photoredox/Lewis acid cooperative catalysis. The compounds may be formulated in a pharmaceutical composition for treating one of the aforementioned diseases or disorders.

  本文披露了萘醌化合物、其类似物以及它们的合成和使用方法。这些化合物可以通过涉及芳基亚甲基丙二酸酯与不饱和亲电试剂的还原缩合方法，利用光还原/路易斯酸协同催化来合成。这些化合物可以配制成药物组合物，用于治疗上述疾病或紊乱之一。
• Intramolecular cycloaddition of N-phthalimidoaziridines to double and triple carbon–carbon bonds
  作者：Alena S. Pankova、Vladimir V. Voronin、Mikhail A. Kuznetsov

  DOI：10.1016/j.tetlet.2009.08.015

  日期：2009.11

  Thermolysis of 3-(2-allyloxyphenyl)- or 3-(2-propargyloxyphenyl)-1-phthalimidoaziridine-2-carboxylic acid derivatives results in stereospecific intramolecular cycloaddition of intermediate N-phthalimidoazomethine ylides to double or triple carbon–carbon bonds. This leads to condensed N-phthalimidopyrrolidines, N-phthalimidopyrrolines, or products of their subsequent transformations. On the other hand

  3-（2-烯丙氧基苯基）-或3-（2-丙炔氧基苯基）-1-邻苯二甲酰氮丙啶-2-羧酸衍生物的热解导致中间体N-邻苯二甲酰亚胺基甲亚胺基团立体定向分子内环加成至双或三碳-碳键。这导致缩合的N-邻苯二甲酰亚胺吡咯烷，N-邻苯二甲酰亚胺吡咯啉或其后续转化的产物。另一方面，类似的3-芳基-1-邻苯二甲酰咪唑啉二甲基-2,2-二羧酸二甲酯的热解仅产生5-甲氧基恶唑，这是竞争性1,5-偶极电环化的产物。
• Black, Michael; Cadogan; McNab, Hamish, Journal of the Chemical Society. Perkin transactions I, 1997, # 17, p. 2483 - 2493
  作者：Black, Michael、Cadogan、McNab, Hamish、MacPherson, Andrew D.、Roddam, V. Peter、Smith, Carol、Swenson, Helen R.

  DOI：——

  日期：——
• C−H Bond Functionalization via Hydride Transfer: Synthesis of Dihydrobenzopyrans from <i>ortho</i>-Vinylaryl Akyl Ethers
  作者：Kevin M. McQuaid、Jonathan Z. Long、Dalibor Sames

  DOI：10.1021/ol900915p

  日期：2009.7.16

  The hydride transfer initiated cyclization ("HT-cyclization") of aryl alkyl ethers, which leads to direct coupling of sp(3) C-H bonds and activated alkenes, is reported. Readily available salicylaldehyde derived ethers are converted in one step to dihydrobenzopyrans, an important class of heteroarenes frequently found in biologically active compounds. This process has not been previously reported, in contrast to known HT-cyclizations of the corresponding tert-amines ("tert-amino effect" reactions).
• Carboxylic esters radical leaving groups: a new and efficient gas-phase synthesis of benzofurans
  作者：Michael Black、J. I. G. Cadogan、Gary A. Cartwright、Hamish McNab、Andrew D. MacPherson

  DOI：10.1039/c39930000959

  日期：——

  Flash vacuum pyrolysis (FVP) of o-allyloxycinnamate esters gives benzofurans in high yield, via cyclisation of a phenoxyl radical and subsequent cleavage of the carboxylic ester function; coumarins are obtained by FVP of the corresponding phenols.

  邻烯丙基肉桂酸酯的闪速真空热解（FVP）可通过苯氧自由基的环化和随后的羧基酯功能裂解，得到高产率的苯并呋喃；相应苯酚的 FVP 可得到香豆素。