2-phenylmethylene-naphtho[2,1-b]furan-1(2H)-one | 88503-21-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: 2-phenylmethylene-naphtho[2,1-b]furan-1(2H)-one
• 英文别名: 2-benzylidene-naphtho[2,1-b]furan-1-one；2-Benzyliden-naphtho[2,1-b]furan-1-on；2-Benzylidenenaphtho[2,1-b]furan-1(2H)-one；2-benzylidenebenzo[e][1]benzofuran-1-one
• CAS: 88503-21-3
• 化学式: C₁₉H₁₂O₂
• 分子量: 272.303
• InChiKey: KVTOUJXIEXWYOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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：

  2-phenylmethylene-naphtho[2,1-b]furan-1(2H)-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 以1.3 g的产率得到2-benzylnaphtho[2,1-b]furan-1(2H)-one
  参考文献：
  名称：

  钯催化脱羧脱芳基不对称烯丙基烷基化的光学活性黄酮类分子

  摘要：

  借助一类新发现的带有手性环烷烃骨架的 Trost 型双膦配体，Pd 催化的苯并呋喃脱羧脱芳基不对称烯丙基烷基化 (AAA) 高效 [0.2-1.0 mol% Pd2(dba)3 /L]，良好的通用性和高对映选择性（> 30 个实例，82-99% 产率和 90-96% ee）。此外，公开了以前无法到达的黄酮类化合物的面向多样性的合成（DOS）。它具有可靠且可扩展的新开发的 Tsuji-Trost-Stoltz AAA 序列、Wacker-Grubbs-Stoltz 氧化、安息香内缩合和共轭加成，可有效构建具有挑战性的紧凑型具有连续立体中心的环戊二烯[b]苯并呋喃支架。该策略为开发基于黄格兰的药物提供了新途径。

  DOI：

  10.1021/jacs.0c05113
• 作为产物：
  描述：

  1-(2-tert-butyldimethylsilyloxynaphthalen-1-yl)-3-phenyl-2-propyn-1-one 在 四丁基氟化铵 作用下， 以72%的产率得到2-phenylmethylene-naphtho[2,1-b]furan-1(2H)-one
  参考文献：
  名称：

  β-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: Improvement of solubility by disruption of molecular planarity

  摘要：

  The physiological role of aryl hydrocarbon receptor (AhR) is not yet fully understood, and investigation is hampered by the limited solubility of reported AhR ligands in aqueous media. To achieve improved solubility, we focused on our previous finding that planarity-disruption of molecules leads to less efficient crystal packing and greater aqueous solubility. Here, we describe chemical modification of an AhR agonist, beta-naphthoflavone, focusing on planarity-disruption. As expected, introduction of substituents at the ortho-positions of the phenyl group resulted in greater solubility. Among the compounds prepared, the fluoro analog showed more potent AhR agonistic activity and greater solubility than did b-naphthoflavone. Our results indicate that this strategy to improve aqueous solubility, that is, introduction of substituent(s) that disrupt planarity, may be generally applicable to bicyclic molecules. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.036

文献信息

• Ingham et al., Journal of the Chemical Society, 1931, p. 895,900
  作者：Ingham et al.

  DOI：——

  日期：——
• Blaser, Jahrb. philos. Fakultaet II Univ. Bern 2 <1922>, 48
  作者：Blaser

  DOI：——

  日期：——
• Optically Active Flavaglines-Inspired Molecules by a Palladium-Catalyzed Decarboxylative Dearomative Asymmetric Allylic Alkylation
  作者：Meng-Yue Cao、Bin-Jie Ma、Zhi-Qi Lao、Hongliang Wang、Jing Wang、Juan Liu、Kuan Xing、Yu-Hao Huang、Kang-Ji Gan、Wei Gao、Huaimin Wang、Xin Hong、Hai-Hua Lu

  DOI：10.1021/jacs.0c05113

  日期：2020.7.15

  With the aid of a class of newly discovered Trost-type bisphosphine ligands bearing a chiral cycloalkane framework, the Pd-catalyzed decarboxylative dearomative asymmetric allylic alkylation (AAA) of benzofurans was achieved with high efficiency [0.2-1.0 mol% Pd2(dba)3/L], good generality and high enantioselectivity (> 30 examples, 82-99% yield and 90-96% ee). Moreover, a diversity-oriented synthesis

  借助一类新发现的带有手性环烷烃骨架的 Trost 型双膦配体，Pd 催化的苯并呋喃脱羧脱芳基不对称烯丙基烷基化 (AAA) 高效 [0.2-1.0 mol% Pd2(dba)3 /L]，良好的通用性和高对映选择性（> 30 个实例，82-99% 产率和 90-96% ee）。此外，公开了以前无法到达的黄酮类化合物的面向多样性的合成（DOS）。它具有可靠且可扩展的新开发的 Tsuji-Trost-Stoltz AAA 序列、Wacker-Grubbs-Stoltz 氧化、安息香内缩合和共轭加成，可有效构建具有挑战性的紧凑型具有连续立体中心的环戊二烯[b]苯并呋喃支架。该策略为开发基于黄格兰的药物提供了新途径。
• β-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: Improvement of solubility by disruption of molecular planarity
  作者：Yuji Fujita、Mitsuhiro Yonehara、Masashi Tetsuhashi、Tomomi Noguchi-Yachide、Yuichi Hashimoto、Minoru Ishikawa

  DOI：10.1016/j.bmc.2009.12.036

  日期：2010.2

  The physiological role of aryl hydrocarbon receptor (AhR) is not yet fully understood, and investigation is hampered by the limited solubility of reported AhR ligands in aqueous media. To achieve improved solubility, we focused on our previous finding that planarity-disruption of molecules leads to less efficient crystal packing and greater aqueous solubility. Here, we describe chemical modification of an AhR agonist, beta-naphthoflavone, focusing on planarity-disruption. As expected, introduction of substituents at the ortho-positions of the phenyl group resulted in greater solubility. Among the compounds prepared, the fluoro analog showed more potent AhR agonistic activity and greater solubility than did b-naphthoflavone. Our results indicate that this strategy to improve aqueous solubility, that is, introduction of substituent(s) that disrupt planarity, may be generally applicable to bicyclic molecules. (C) 2010 Elsevier Ltd. All rights reserved.