3-cyano-4,5,7-trimethoxy-1(3H)-isobenzofuranone | 116664-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-cyano-4,5,7-trimethoxy-1(3H)-isobenzofuranone
• 英文别名: 4,6,7-trimethoxy-3-oxo-1H-2-benzofuran-1-carbonitrile
• CAS: 116664-70-1
• 化学式: C₁₂H₁₁NO₅
• 分子量: 249.223
• InChiKey: WNVPFCQOEAHPHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-cyano-4,5,7-trimethoxy-1(3H)-isobenzofuranone 、 (E,E)-6',7'-dihydro-9'-methoxy-3'-(1,3-pentadienyl)spiro<3-cyclopentene-1,8'-cyclopentisoquinoline>-2,5-(2'H)-dione 在 lithium diisopropyl amide 作用下， 生成 4,6,7-trimethoxy-1-[9-methoxy-1,2',4'-trioxo-3-[(1E,3E)-penta-1,3-dienyl]spiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,3'-cyclopentane]-1'-yl]-3-oxo-2-benzofuran-1-carbonitrile
  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：

  2,4,5-三甲氧基苯甲酰氯 在 盐酸 、 四甲基乙二胺 、 仲丁基锂 、 溶剂黄146 作用下， 以 水 、 苯 为溶剂， 反应 49.5h， 生成 3-cyano-4,5,7-trimethoxy-1(3H)-isobenzofuranone
  参考文献：
  名称：

  Diels-Alder approaches to model compounds related to fredericamycin A

  摘要：

  DOI：

  10.1021/jo00258a022

文献信息

• Total Syntheses of HMP-Y1, Hibarimicinone, and HMP-P1
  作者：Brian B. Liau、Benjamin C. Milgram、Matthew D. Shair

  DOI：10.1021/ja307207q

  日期：2012.10.10

  Total syntheses of HMP-Y1, atrop-HMP-Y1, hibarimicinone, atrop-hibarimicinone, and HMP-P1 are described using a two-directional synthesis strategy. A novel benzyl fluoride Michael-Claisen reaction sequence was developed to construct the complete carbon skeleton of HMP-Y1 and atrop-HMP-Y1 via a symmetrical, two-directional, double annulation. Through efforts to convert HMP-Y1 derivatives to hibarimicinone

  使用双向合成策略描述了 HMP-Y1、atrop-HMP-Y1、hibarimicinone、atrop-hibarimicinone 和 HMP-P1 的总合成。开发了一种新的苄基氟迈克尔-克莱森反应序列，通过对称、双向、双环化来构建 HMP-Y1 和 atrop-HMP-Y1 的完整碳骨架。通过将 HMP-Y1 衍生物转化为 Hibarimicinone 和 HMP-P1，实现了仿生单氧化使受保护的 HMP-Y1 去对称化。开发了一种双向不对称双环化和仿生醚化，以构建多环和高度氧化的 Hibarimicinone、atrop-hibarimicinone 和 HMP-P1 骨架。使用外消旋联芳基前体可以合成两种 Hibarimicinone 阻转异构体，并首次证实了 atrop-hibarimicinone 的结构。此外，这项工作记录了首次报道的 atrop-hibarimicinon
• Saint-Jalmes, L.; Lila, C.; Xu, J. Z., Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 447 - 449
  作者：Saint-Jalmes, L.、Lila, C.、Xu, J. Z.、Moreau, L.、Pfeiffer, B.、et al.

  DOI：——

  日期：——
• EVANS, JONATHAN C.;KLIX, RUSSELL C.;BACH, ROBERT D., J. ORG. CHEM., 53,(1988) N 23, C. 5519-5527
  作者：EVANS, JONATHAN C.、KLIX, RUSSELL C.、BACH, ROBERT D.

  DOI：——

  日期：——
• Diels-Alder approaches to model compounds related to fredericamycin A
  作者：Jonathan C. Evans、Russell C. Klix、Robert D. Bach

  DOI：10.1021/jo00258a022

  日期：1988.11
• 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.