6'-bromo-2',3'-dihydro-7'-methoxy-5'-methylspiro-2,5-dione bis(ethylene acetal) | 158304-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6'-bromo-2',3'-dihydro-7'-methoxy-5'-methylspiro-2,5-dione bis(ethylene acetal)
• CAS: 158304-72-4
• 化学式: C₁₉H₂₃BrO₅
• 分子量: 411.293
• InChiKey: IQWPUBZNAMKQNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6'-bromo-2',3'-dihydro-7'-methoxy-5'-methylspiro-2,5-dione bis(ethylene acetal) 在 盐酸 、 正丁基锂 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 氨 、 phenyltrimethylammonium tribromide 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 96.34h， 生成 (E,E)-6',7'-dihydro-9'-methoxy-3'-(1,3-pentadienyl)spiro<3-cyclopentene-1,8'-cyclopentisoquinoline>-2,5-(2'H)-dione
  参考文献：
  名称：

  Synthesis of (.+-.)-Fredericamycin A

  摘要：

  The synthesis of (+/-)-fredericamycin A (1) is reported with full experimental detail. Preparations of building blocks for the upper (2) and lower (3) units of 1 are described. The union of 2 and 3 by a two-step 1,4-dipolar cycloaddition and the elaboration of the resulting product (19) into 1 are presented. The spiro 1,3-dione center in 1 was introduced utilizing a mild mercury-mediated pinacol rearrangement involving a 1,2-carbonyl migration. The reaction of benzylic cuprate anions ortho to aromatic esters has been shown to produce isochromarins in good yield. These isochromarins afford the biologically relevant isoquinolones upon treatment with ammonia.

  DOI：

  10.1021/ja00101a013
• 作为产物：
  描述：

  3,3-Bis(ethylsulfanyl)-6-methyl-1,2-dihydroinden-4-ol 在 N-溴代丁二酰亚胺(NBS) 、 mercury(II) trifluoroacetate 、 potassium hydride 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 67.0h， 生成 6'-bromo-2',3'-dihydro-7'-methoxy-5'-methylspiro-2,5-dione bis(ethylene acetal)
  参考文献：
  名称：

  Synthesis of (.+-.)-Fredericamycin A

  摘要：

  The synthesis of (+/-)-fredericamycin A (1) is reported with full experimental detail. Preparations of building blocks for the upper (2) and lower (3) units of 1 are described. The union of 2 and 3 by a two-step 1,4-dipolar cycloaddition and the elaboration of the resulting product (19) into 1 are presented. The spiro 1,3-dione center in 1 was introduced utilizing a mild mercury-mediated pinacol rearrangement involving a 1,2-carbonyl migration. The reaction of benzylic cuprate anions ortho to aromatic esters has been shown to produce isochromarins in good yield. These isochromarins afford the biologically relevant isoquinolones upon treatment with ammonia.

  DOI：

  10.1021/ja00101a013

文献信息

• Synthesis of (.+-.)-Fredericamycin A
  作者：John A. Wendt、Paul J. Gauvreau、Robert D. Bach

  DOI：10.1021/ja00101a013

  日期：1994.11

  The synthesis of (+/-)-fredericamycin A (1) is reported with full experimental detail. Preparations of building blocks for the upper (2) and lower (3) units of 1 are described. The union of 2 and 3 by a two-step 1,4-dipolar cycloaddition and the elaboration of the resulting product (19) into 1 are presented. The spiro 1,3-dione center in 1 was introduced utilizing a mild mercury-mediated pinacol rearrangement involving a 1,2-carbonyl migration. The reaction of benzylic cuprate anions ortho to aromatic esters has been shown to produce isochromarins in good yield. These isochromarins afford the biologically relevant isoquinolones upon treatment with ammonia.