2-Isopropoxy phenyl-methylene-propanedioic acid dimethyl ester | 130451-85-3

• 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: 2-Isopropoxy phenyl-methylene-propanedioic acid dimethyl ester
• 英文别名: Dimethyl 2-[(2-propan-2-yloxyphenyl)methylidene]propanedioate
• CAS: 130451-85-3
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: KFZIZDYCQQPMAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-Isopropoxy phenyl-methylene-propanedioic acid dimethyl ester 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以91%的产率得到dimethyl 2,2-dimethyl-4H-chromene-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：

  2-异丙氧基苯甲醛 、 丙二酸二甲酯 在 哌啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 以2.13 g的产率得到2-Isopropoxy phenyl-methylene-propanedioic acid dimethyl ester
  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

文献信息

• Mechanism of decarbalkoxylation of arylmethylene-propanedioic acid dimethyl esters
  作者：Angela M. Bernard、Giovanni Cerioni、Pier Paolo Piras

  DOI：10.1016/s0040-4020(01)90528-9

  日期：1990.1

  The decarbalkoxylation in DMSO-NaX-H2 O, of some arylmethylene propanedioic acid dimethyl esters is studied. Both the relative rates of the para (R = NO2, H, CH3, OCH3) and the ortho [R = H, OCH3 , OCH(CH3)2]substituted aryl derivatives, together with the stereochemical outcome, support a preliminary nucleophilic attack by water followed by decarbalkoxylative elimination.

  研究了一些芳基亚甲基丙二酸二甲酯在DMSO-NaX-H 2 O中的脱碳烷氧基化反应。对位（R = NO 2，H，CH 3，OCH 3）和邻位[R = H，OCH 3，OCH（CH 3）2 ]取代的芳基衍生物的相对速率以及立体化学结果均支持用水引起的初步亲核攻击，然后进行脱羧烷氧基化消除。
• BERNARD, ANGELA M.;CERIONI, GIOVANNI;PIRAS, PIER PAOLO, TETRAHEDRON., 46,(1990) N1, C. 3929-3940
  作者：BERNARD, ANGELA M.、CERIONI, GIOVANNI、PIRAS, PIER PAOLO

  DOI：——

  日期：——