4-Methoxy-9-phenyl-3H-naphtho[2,3-c]furan-1-one | 80466-41-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 4-Methoxy-9-phenyl-3H-naphtho[2,3-c]furan-1-one
• 英文别名: 4-methoxy-9-phenyl-3H-benzo[f][2]benzofuran-1-one
• CAS: 80466-41-7
• 化学式: C₁₉H₁₄O₃
• 分子量: 290.318
• InChiKey: ZPEIYOHQDNUALT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Methoxy-9-phenyl-3H-naphtho[2,3-c]furan-1-one 生成 5-hydroxy-10-phenyl-2,3-dihydro-1H-benzo[g]phthalazin-4-one
  参考文献：
  名称：

  KREPELKA, J.;VANCUROVA, I.;ROUBIK, J.;SEMONSKY, M.

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methoxymethyl-α-phenylbenzyl alcohol 在 palladium on activated charcoal 吡啶 、 氯化亚砜 、 Celite 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.5h， 生成 4-Methoxy-9-phenyl-3H-naphtho[2,3-c]furan-1-one
  参考文献：
  名称：

  A Convenient Method for the Synthesis of9-Aryl-4-methoxynaphtho[2,3-c]furan-1(3H)-ones

  摘要：

  A three-step procedure for the synthesis of the title lignan lactone derivatives is described. The route involves a tandem Michael addition/cyclization reaction between o-aroyl-alpha-methoxybenzyllithiums, which are generated in situ by the treatment of aryl 2-methoxymethylphenyl ketones with lithium diisopropylamide (LDA) in THF at -78 degrees C, and furan-2(5H)-one to give the corresponding 9-aryl-9-hydroxy-4-methoxy-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1 (3H)-ones in moderate to good yields. These products are readily transformed into the title naphthofuranones by dehydration with thionyl. chloride in pyridine, followed by aromatization with palladium on activated carbon.

  DOI：

  10.3987/com-97-7864

文献信息

• Sequential and regioselective Friedel-Crafts reactions of gem-dihalocyclopropanecarbonyl chlorides with benzenes for the synthesis of 4-aryl-l-naphthol derivatives
  作者：Yoshinori Nishii、Yoo Tanabe

  DOI：10.1016/0040-4039(95)01866-g

  日期：1995.11

  Two types of novel, sequential and regioselective Friedel-Crafts reactions of gem-dihalocyclopmpanecarbonyl chlorides with benzenes proceeded in a one-pot manner, E-3-aryl-2,2-dihalo-cyclopropanecarbonyl chlorides reacted with substituted benzenes to afford 4-aryl-3-halo- l-naphthols, while 2,2-dichlorocyclopropanecarbonyl chlorides were transformed into 4-aryl-l-naphthols in benzene or p-xylene, Both

  宝石-二卤代环丙烷羰基氯化物与苯的两种新颖的，顺序的和区域选择性的弗瑞德-克来福特反应以一锅法进行，E -3-芳基-2,2-二卤代环丙烷羰基氯化物与取代的苯反应得到4-芳基-3-卤代-1-萘，而2,2-二氯环丙烷羰基氯在苯或对二甲苯中转化为4-芳基-1-萘，两种环合均涉及交替和高度区域选择性的环丙烷开环。
• Sequential and regioselective Friedel–Crafts reactions of gem-dihalogenocyclopropanecarbonyl chlorides with benzenes for the synthesis of 4-aryl-1-naphthol derivatives
  作者：Yoshinori Nishii、Yoo Tanabe

  DOI：10.1039/a605030a

  日期：——

  Novel, sequential and regioselective Friedel–Crafts type reactions of (E)-3-aryl-2,2-dihalogenocyclopropanecarbonyl chlorides 1 and 2,2-dichlorocyclopropanecarbonyl chlorides 3 with benzenes produce various 4-aryl-3-halogeno-1-naphthols 2 and 4-aryl-1-naphthols 4, respectively. One of the benzannulations involves the intramolecular cyclization of acid chlorides 1, followed by intermolecular coupling with substituted benzenes to give 4-aryl-3-halogeno-1-naphthols 2. As a demonstration of this annulation, 4-aryl-3-bromo-1-naphthols 2i and 2k are successfully converted into new analogues of 1-aryl-3-hydroxymethyl-4-methoxy-2-naphthoic acid lactones 13, a class of lignan lactones. The other benzannulation involves three series of reactions using acid chlorides 3a–c: (1) the intermolecular Friedel–Crafts acylation of 3 with one benzene molecule giving the intermediary 2,2-dichlorocyclopropyl(phenyl)methanones 14a–c; (2) the intermolecular trapping of 14a–c with another benzene molecule accompanied by regioselective ring opening; and (3) the final intramolecular cyclization giving 4-phenyl-1-naphthols 4a–c. The use of p-xylene also gives the corresponding 4-(p-xylyl)-1-naphthol 4d. The reactions of alternatively prepared ketones 14 with benzenes gives a variety of ‘unsymmetrically’ substituted 4-aryl-1-naphthols 4c,e–k under identical conditions. However, the reaction using p-methoxyphenyl ketone analogues 14g does not produce 4-aryl-1-naphthols, but gives 5-aryl-2-(p-methoxyphenyl)-3-methylfurans 16. These annulations proceed straightforwardly (in a one-pot manner) and this variation is due to the highly regioselective cyclopropane ring-openings.

  新颖的、顺序的以及区域选择性的Friedel-Crafts类反应，通过苯与(E)-3-芳基-2,2-二卤代环丙烷羧酰氯1和2,2-二氯环丙烷羧酰氯3发生反应，生成各种4-芳基-3-卤代-1-萘醇2和4-芳基-1-萘醇4。其中一类苯环增殖反应涉及酸氯1的分子内环化，随后与取代苯的分子间耦合，生成4-芳基-3-卤代-1-萘醇2。作为这一环增殖反应的示范，成功将4-芳基-3-溴-1-萘醇2i和2k转化为新的1-芳基-3-羟甲基-4-甲氧基-2-萘酸内酯类化合物13，这是一类木质素内酯。另一类苯环增殖反应涉及使用酸氯3a-c进行三系列反应：（1）与一个苯分子的分子间Friedel-Crafts酰基化反应，得到中间体2,2-二氯环丙基（苯基）甲酮14a-c；（2）与另一个苯分子的分子间捕捉14a-c，伴随区域选择性的开环；（3）最终的分子内环化反应生成4-苯基-1-萘醇4a-c。使用对二甲苯也能得到相应的4-(对二甲基基)-1-萘醇4d。交替制备的酮14与苯的反应在相同条件下生成多种“不对称”取代的4-芳基-1-萘醇4c,e-k。然而，使用对甲氧基苄基酮类化合物14g的反应并不产生4-芳基-1-萘醇，而是生成5-芳基-2-(对甲氧基苄基)-3-甲基呋喃16。这些环增殖反应在单锅条件下直接进行，这种变化是由于高度区域选择性的环丙烷开环反应造成的。
• KREPELKA, J.;VANCUROVA, I.;ROUBIK, J.;SEMONSKY, M.
  作者：KREPELKA, J.、VANCUROVA, I.、ROUBIK, J.、SEMONSKY, M.

  DOI：——

  日期：——
• Krepelka, Jiri; Holubek, Jiri, Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 9, p. 2123 - 2128
  作者：Krepelka, Jiri、Holubek, Jiri

  DOI：——

  日期：——
• Krepelka, Jiri; Vancurova, Iva; Holubek, Jiri, Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 4, p. 1252 - 1257
  作者：Krepelka, Jiri、Vancurova, Iva、Holubek, Jiri

  DOI：——

  日期：——