2,2-diphenylbenzo(1,3-dioxole)-5-carboxylic acid methyl ester | 65638-94-0

• 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: 2,2-diphenylbenzo(1,3-dioxole)-5-carboxylic acid methyl ester
• 英文别名: Methyl 2,2-diphenyl-1,3-benzodioxole-5-carboxylate
• CAS: 65638-94-0
• 化学式: C₂₁H₁₆O₄
• 分子量: 332.356
• InChiKey: ABOQOJCHLDRHMD-UHFFFAOYSA-N

物化性质

• 熔点：
  98.0-99.5 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  466.9±45.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-diphenylbenzo(1,3-dioxole)-5-carboxylic acid methyl ester 在 manganese(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 正丁基锂 、 对甲苯磺酸 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 19.67h， 生成 2,2-Diphenyl-6-triethylsilyl-1,3-benzodioxole-5-carbaldehyde
  参考文献：
  名称：

  Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids

  摘要：

  By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (+/-)-sanguinine and the total syntheses of (+/-)-galanthamine, (+/-)-narwedine, (+/-)-lycoramine, and (+/-)-norgalanthamine were also successfully carried out.

  DOI：

  10.1021/jo9807868
• 作为产物：
  描述：

  原儿茶酸 在 硫酸 作用下， 反应 9.17h， 生成 2,2-diphenylbenzo(1,3-dioxole)-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids

  摘要：

  By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (+/-)-sanguinine and the total syntheses of (+/-)-galanthamine, (+/-)-narwedine, (+/-)-lycoramine, and (+/-)-norgalanthamine were also successfully carried out.

  DOI：

  10.1021/jo9807868

文献信息

• Linker-modified quinoline derivatives targeting HIV-1 integrase: synthesis and biological activity
  作者：Christophe Bénard、Fatima Zouhiri、Marie Normand-Bayle、Michèle Danet、Didier Desmaële、Hervé Leh、Jean-François Mouscadet、Gladys Mbemba、Claire-Marie Thomas、Sabine Bonnenfant、Marc Le Bret、Jean d'Angelo

  DOI：10.1016/j.bmcl.2004.03.005

  日期：2004.5

  A novel series of HIV-1 integrase inhibitors was synthesized and tested in both in vitro and ex vivo assays. These inhibitors are featured by the presence of a quinoline subunit and an ancillary aromatic ring linked by functionalized spacers such as amide, hydrazide, urea and 1-hydroxyprop-l-en-3-one moiety. Amide derivatives are the most promising ones and could serve as leads for further developments. (C) 2004 Elsevier Ltd. All rights reserved.
• PATCHETT, A. A.;TAUB, D.
  作者：PATCHETT, A. A.、TAUB, D.

  DOI：——

  日期：——
• Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids
  作者：Yasuyuki Kita、Mitsuhiro Arisawa、Michiyo Gyoten、Makiko Nakajima、Ryuji Hamada、Hirofumi Tohma、Takeshi Takada

  DOI：10.1021/jo9807868

  日期：1998.9.1

  By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (+/-)-sanguinine and the total syntheses of (+/-)-galanthamine, (+/-)-narwedine, (+/-)-lycoramine, and (+/-)-norgalanthamine were also successfully carried out.