4,9-dihydro-4-(hydroxymethyl)-4-methyl-9-oxonaphtho[2,3-b]furan-3-carboxylic acid | 950906-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 4,9-dihydro-4-(hydroxymethyl)-4-methyl-9-oxonaphtho[2,3-b]furan-3-carboxylic acid
• 英文别名: 4-(Hydroxymethyl)-4-methyl-9-oxobenzo[f][1]benzofuran-3-carboxylic acid
• CAS: 950906-69-1
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: MIMKGVMGMHROEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,9-dihydro-4-(hydroxymethyl)-4-methyl-9-oxonaphtho[2,3-b]furan-3-carboxylic acid 在 吡啶 、 2,4,6-三异丙基苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以54%的产率得到
  参考文献：
  名称：

  Furanosteroid Studies. Stereoselective Synthesis of the A,B,E-Ring Core of Wortmannin

  摘要：

  Alkyne oxazole 11c is converted in three steps, and similar to 45% overall yield, to furanolactone 21 alpha having the A,B,E-ring core of the wortmannin (2) family of furanosteroids. The TiCl4-catalyzed insertion of EtO2C-CHO between C-3 and C-10 in furanoacid 14d is > 98% stereoselective via a pathway involving chemoselective lactonization of equilibrating aldol intermediates 23 alpha,beta (dynamic kinetic resolution).

  DOI：

  10.1021/ol071158s
• 作为产物：
  描述：

  benzyl 4,9-dihydro-4-(hydroxymethyl)-4-methyl-9-oxonaphtho[2,3-b]furan-3-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 为溶剂， 以82%的产率得到4,9-dihydro-4-(hydroxymethyl)-4-methyl-9-oxonaphtho[2,3-b]furan-3-carboxylic acid
  参考文献：
  名称：

  Furanosteroid Studies. Stereoselective Synthesis of the A,B,E-Ring Core of Wortmannin

  摘要：

  Alkyne oxazole 11c is converted in three steps, and similar to 45% overall yield, to furanolactone 21 alpha having the A,B,E-ring core of the wortmannin (2) family of furanosteroids. The TiCl4-catalyzed insertion of EtO2C-CHO between C-3 and C-10 in furanoacid 14d is > 98% stereoselective via a pathway involving chemoselective lactonization of equilibrating aldol intermediates 23 alpha,beta (dynamic kinetic resolution).

  DOI：

  10.1021/ol071158s

文献信息

• Method for synthesizing furanosteroids
  申请人：Jacobi Peter A.

  公开号：US20090143346A1

  公开（公告）日：2009-06-04

  The present invention is a method for synthesizing furanosteroids. The method involves intramolecular Diels-Alder/retro-Diels-Alder reaction and tautomerization of a functionalized alkyne oxazole to produce a furo[2,3-b]phenol derivative which is elaborated by intermolecular and intramolecular condensations to generate ring-A of the furanosteroid. Furanosteroids and pharmaceutical compositions containing the same are also provided.

  本发明涉及一种合成呋喃甾体的方法。该方法涉及分子内Diels-Alder/retro-Diels-Alder反应和一个官能化炔基噁唑的异构化，以产生一种furo[2,3-b]苯酚衍生物，通过分子间和分子内缩合反应来生成呋喃甾体的A环。同时还提供了呋喃甾体和含有其的药物组合物。
• US8067583B2
  申请人：——

  公开号：US8067583B2

  公开（公告）日：2011-11-29
• Furanosteroid Studies. Stereoselective Synthesis of the A,B,E-Ring Core of Wortmannin
  作者：E. Hampton Sessions、Roger T. O'Connor、Peter A. Jacobi

  DOI：10.1021/ol071158s

  日期：2007.8.1

  Alkyne oxazole 11c is converted in three steps, and similar to 45% overall yield, to furanolactone 21 alpha having the A,B,E-ring core of the wortmannin (2) family of furanosteroids. The TiCl4-catalyzed insertion of EtO2C-CHO between C-3 and C-10 in furanoacid 14d is > 98% stereoselective via a pathway involving chemoselective lactonization of equilibrating aldol intermediates 23 alpha,beta (dynamic kinetic resolution).