6-carbethoxyphthalide | 96259-62-0

• 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: 6-carbethoxyphthalide
• 英文别名: ethyl 3-oxo-1,3-dihydroisobenzofuran-5-carboxylate；ethyl 3-oxo-1H-2-benzofuran-5-carboxylate
• CAS: 96259-62-0
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: RNKCOEWUOUEICD-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C(Solv: ethanol (64-17-5))
• 沸点：
  403.7±45.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-carbethoxyphthalide 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 水 作用下， 以 四氢呋喃 、 四氯化碳 、 乙酸乙酯 为溶剂， 反应 73.0h， 生成 Methyl 6-methyl-5,11-dioxoindeno[1,2-c]isoquinoline-3-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Indenoisoquinoline Rexinoids with Chemopreventive Potential

  摘要：

  Nuclear receptors, such as the retinoid X receptor (RXR), are proteins that regulate a myriad of cellular processes. Molecules that function as RXR agonists are of special interest for the prevention and control of carcinogenesis. The majority of these ligands possess an acidic moiety that is believed to be key for RXR activation. This communication presents the design, synthesis, and biological evaluation of both acidic and nonacidic indenoisoquinolines as new RXR ligands. In addition, a comprehensive structure-activity relationship study is presented that identifies the important features of the indenoisoquinoline rexinoids. The ease of modification of the indenoisoquinoline core and the lack of the necessity of a carboxyl group for activity make them an attractive and unusual family of RXR agonists. This work establishes a structural foundation for the design of new and novel rexinoid cancer chemopreventive agents.

  DOI：

  10.1021/jm400026k
• 作为产物：
  描述：

  4-甲基-异酞腈 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 水 作用下， 以 四氯化碳 、 二乙二醇 为溶剂， 反应 48.0h， 生成 6-carbethoxyphthalide
  参考文献：
  名称：

  Substituent effects on hydrogenation of aromatic rings: hydrogenation vs. hydrogenolysis in cyclic analogs of benzyl ethers

  摘要：

  DOI：

  10.1021/jo00212a025

文献信息

• Synthesis of Isobenzofuranones by Cobalt Catalyzed [2+2+2] Cycloaddition
  作者：Carolina Méndez-Gálvez、Matthias Böhme、Reko Leino、Risto Savela

  DOI：10.1002/ejoc.202000046

  日期：2020.3.22

  Transition metal‐catalyzed [2+2+2] cyclotrimerization is a powerful method to synthesize substituted benzene derivatives with optimal atom efficiency. However, controlling regio‐ and chemoselectivity is difficult. We present a cobalt catalyzed cycloaddition of alkynes, which provides the cycloaddition products in high yields and excellent regioselectivity in the presence of a pyridine‐2,6‐diimine ligand

  过渡金属催化的[2 + 2 + 2]环三聚是一种以最佳原子效率合成取代苯衍生物的有效方法。但是，很难控制区域选择性和化学选择性。我们提出了炔烃的钴催化环加成反应，该反应可在吡啶-2,6-二亚胺配体存在下以高收率和出色的区域选择性提供环加成产物。
• Cyclotrimerization of acetylenes catalyzed by (η5-cyclopentadienyl)rhodium complexes
  作者：Khalid Abdulla、Brian L. Booth、Catherine Stacey

  DOI：10.1016/0022-328x(85)80250-3

  日期：1985.9

  comparative rates of cyclotrimerization of dimethylacetylenedicarboxylate (DMAD) and hex-3-yne have been studied with the catalysts [η5-C5R5)Rh(COD)] (R = H, Me, Cl; COD = cycloocta-1,5-diene), [(η5-C5R5)Rh(CO)2] (R = H, Me), [(η5-C5Me5RhL2] (L = C2H4, PF3) and [(η5-C5H4PPh3)Rh(CO)2]+ PF6− under pseudo-first-order conditions. In these reactions, which all obey the rate law, rate = kobs [acetylene], the rate

  丁炔二酸二甲酯（DMAD）和环化三聚的比较率己-3-炔已经研究了与催化剂[η 5 -C 5 - [R 5）的Rh（COD）]（R = H，Me中的氯; COD =环辛1 ，5-二烯），[（η 5 -C 5 - [R 5）的Rh（CO）2 ]（R = H，Me）时，[（η 5 -C 5我5 RHL 2 ]（L = C 2 H ^ 4， PF 3）和[（η 5 -C 5 H ^ 4 PPH 3）的Rh（CO）2 ] + PF 6 -在伪一阶条件下。在这些均符合速率定律的反应中，速率= k obs [乙炔]，随着环戊二烯基配体的π-受体强度增加，DMAD的环三聚速率降低，并且在hex-3-反应中这种趋势被逆转恩。环三聚的速率也出现与配位体L的性质改变（其中L = C 2 H ^ 4，CO，PF 3，12 COD）暗示使得L遗体结合于铑原子在整个催化循环。初步研究表明，在某些情况下，选择性共低聚发
• Synthesis of phthalides from bis-propargyl ethers: use of Garratt–Braverman cyclization to construct the phthalans and IBX as a new reagent for subsequent oxidation
  作者：Arpita Panja、Eshani Das、Manasi Maji、Amit Basak

  DOI：10.1016/j.tetlet.2015.09.036

  日期：2015.10

  An efficient route to phthalides is described starting from easily available bis-propargyl ethers. The method involves Garratt-Braverman cyclization of the ethers to phthalans which are then efficiently oxidized to the phthalides by iodoxy benzoic acid (IBX) which has been shown to be a superior reagent in terms of yield and reagent stoichiometry for such a transformation in comparison with more commonly used KMnO4/CuSO4 reagent. (C) 2015 Elsevier Ltd. All rights reserved.
• ANZALONE, L.;HIRSCH, J. A., J. ORG. CHEM., 1985, 50, N 12, 2128-2133
  作者：ANZALONE, L.、HIRSCH, J. A.

  DOI：——

  日期：——
• US4189171A
  申请人：——

  公开号：US4189171A

  公开（公告）日：1980-02-19