(Z)-3-(naphthalen-1-ylmethylene)isobenzofuran-1(3H)-one | 38144-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-3-(naphthalen-1-ylmethylene)isobenzofuran-1(3H)-one
• 英文别名: (Z)-3-(1-naphthylmethylene)isobenzofuran-1-one；3-Naphthalen-1-ylmethylene-3H-isobenzofuran-1-one；(3Z)-3-(naphthalen-1-ylmethylidene)-2-benzofuran-1-one
• CAS: 38144-82-0
• 化学式: C₁₉H₁₂O₂
• 分子量: 272.303
• InChiKey: JRLHCXITJGWLCS-PDGQHHTCSA-N

物化性质

• 沸点：
  467.7±45.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3-(naphthalen-1-ylmethylene)isobenzofuran-1(3H)-one 在 磷化氢 、 氢碘酸 作用下， 生成 2-(2-萘-1-基乙基)苯甲酸
  参考文献：
  名称：

  Fulvenes and Thermochromic Ethylenes. XXXIII.¹ Polycyclic Derivatives of Heptafulvene

  摘要：

  DOI：

  10.1021/jo01047a015
• 作为产物：
  描述：

  1-乙炔基萘 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (Z)-3-(naphthalen-1-ylmethylene)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Systematic Modifications of a Simple Tolan: Another Category of Viscosity Sensor

  摘要：

  The first tolan derivative-based viscosity sensor (5d) has been synthesized, and its fluorescence intensity and lifetime increase when the viscosity of the solvent increases in methanol glycerol mixtures. Phthalide (5d) was selected among structurally diverse tolan derivatives through systematic modifications of a simple tolan. To test 5d as a viscosity sensor, fluorescence lifetime imaging (FLIM) images of HeLa cells were obtained upon treatment with 5 irM of 5d to map the viscosity of the HeLa cells.

  DOI：

  10.1021/acs.orglett.9b04050

文献信息

• Synthesis of phthalides through palladium-catalysed heteroannulation of acetylenic compounds
  作者：Nitya G. Kundu、Manojit Pal

  DOI：10.1039/c39930000086

  日期：——

  The reaction of o-iodobenzoic acid with various acetylenic compounds in the presence of a palladium catalyst leads to phthalides [1-(3H)isobenzofuran-3-ones] as major products and isocoumarins as minor products.

  邻碘苯甲酸与各种乙炔化合物在钯催化剂的存在下反应，主要生成酞烯 [1-(3H)异苯并呋喃-3-酮]，少量生成异香豆素。
• Palladium-catalysed heteroannulation with terminal alkynes: synthesis of phthalides 1
  作者：Nitya G. Kundu、Manojit Pal、Bidisha Nandi

  DOI：10.1039/a705450e

  日期：——

  The palladium–copper-catalysed heteroannulation of o-iodobenzoic acid 3 with terminal alkynes 4–18 leads to the synthesis of (Z)-3-alkylidenephthalides 19–33 as the major products. In certain cases, the formation of isocoumarins 34–37 is also observed.

  钯-铜催化的o-碘苯甲酸3与末端炔烃4-18的杂环化反应主要合成得到(Z)-3-烷亚基苯并呋喃19-33。在某些情况下，也会观察到异香豆素34-37的形成。
• Ir‐SpinPHOX Catalyzed Enantioselective Hydrogenation of 3‐Ylidenephthalides
  作者：Yao Ge、Zhaobin Han、Zheng Wang、Chen‐Guo Feng、Qian Zhao、Guo‐Qiang Lin、Kuiling Ding

  DOI：10.1002/anie.201807639

  日期：2018.10

  The first asymmetric hydrogenation of 3‐ylidenephthalides has been developed using the IrI complex of a spiro[4,4]‐1,6‐nonadiene‐based phosphine‐oxazoline ligand (SpinPHOX) as the catalyst, affording a wide variety of chiral 3‐substituted phthalides in excellent enantiomeric excesses (up to 98 % ee). The utility of the protocol has been demonstrated in the asymmetric synthesis of chiral drugs NBP and

  使用基于螺[4,4] -1,6-壬二烯的膦-恶唑啉配体（SpinPHOX）的Ir I络合物作为催化剂开发了3种亚萘二甲酸酯的第一个不对称氢化反应，提供了多种手性3出色的对映体过量（最高ee达98％）的预取代邻苯二甲酸酯。该协议的实用性已在手性药物NBP和BZP前体以及天然产物创心酚和邻苯二甲酰亚胺的不对称合成中得到证明。
• Microwaves assisted Gabriel synthesis of phthalides
  作者：Margita Lácová、Jarmila Chovancová、Eva Veverková、Štefan Toma

  DOI：10.1016/0040-4020(96)00922-2

  日期：1996.11

  Cesium acetate was found to be the best catalyst for the synthesis of 3-benzylidenephthalide from phthalic anhydride and phenylacetic acid. Reasonable to good yields of different 3-arylmethylenephthalides were isolated from the microwave Gabriel synthesis, even when phenylthio- and 2-(3-)thienyl- acetic acids were used as the starting material.

  发现乙酸铯是从邻苯二甲酸酐和苯乙酸合成3-苄叉二苯酞的最佳催化剂。即使使用苯硫基和2-（3-）噻吩基-乙酸作为原料，从微波Gabriel合成中也可以分离出具有合理收率的不同3-芳基亚甲基邻苯二甲酸酯。
• Synthesis, Bioevaluation and Structural Study of Substituted Phthalazin-1(2H)-ones Acting as Antifungal Agents
  作者：Marcos Derita、Esther del Olmo、Bianca Barboza、Ana García-Cadenas、José López-Pérez、Sebastián Andújar、Daniel Enriz、Susana Zacchino、Arturo San Feliciano

  DOI：10.3390/molecules18033479

  日期：——

  important yeasts and filamentous fungi. Among them, the compound 4-(4-chlorobenzyl)-2-methylphthalazin-1(2H)-one (5) exhibited a remarkable antifungal activity against standardised strains of dermatophytes and Cryptococcus neoformans, as well as against some clinical isolates. A physicochemical study performed on compound 5 revealed its conformational and electronic characteristics, providing us with useful

  合成了 25 种多取代的酞嗪酮衍生物，并测试了它们对一组致病性和临床上重要的酵母菌和丝状真菌的抗真菌活性。其中，化合物 4-(4-chlorobenzyl)-2-methylphthalazin-1(2H)-one (5) 对皮肤癣菌和新型隐球菌的标准化菌株以及一些临床分离株表现出显着的抗真菌活性。对化合物 5 进行的物理化学研究揭示了其构象和电子特性，为我们未来设计新型相关抗真菌类似物提供了有用的数据。