4-benzyloxycarbonyloxy-2-methyl-1(2H)-isoquinolinone | 154550-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-benzyloxycarbonyloxy-2-methyl-1(2H)-isoquinolinone
• 英文别名: benzyl (2-methyl-1-oxoisoquinolin-4-yl) carbonate
• CAS: 154550-16-0
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: LHGMIOHKBOVXOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-benzyloxycarbonyloxy-2-methyl-1(2H)-isoquinolinone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 7.85h， 生成 (1α,2aα,8bα)-(+/-)-8b-1-cyano-8b-hydroxy-1,2a,3,8b-tetrahydro-3-methylcyclobutisoquinolin-4(2H)-one
  参考文献：
  名称：

  Photoinduced Molecular Transformations. part 147. [2+2]Photoaddition of Protected 4-Hydroxy-1(2H)-isoquinolinone with an Electrondeficient Alkene and the Formation of a 3,6-Epoxy-3,4,5,6-tetrahydro-2-benzazocin-1(2H)-one via a b-Scission of Cyclobutanoxyl Radicals Generated from the Resulting photoadduct

  摘要：

  The direct irradiation of 4-benzyloxycarbonyloxy-2-methyl-1(2H)-isoquinolinone gave a 1 to 1 ratio of two stereoisomers of [2+2] photoadducts in 97% yield. Removal of the protecting group from the adducts by hydrogenolysis gave the corresponding cyclobutanols, (1 alpha, 2a alpha, 8b alpha)-(+/-)-1-cyano-1,2a,3,8b-tetrahydro-8 b-hydroxy-3 -methylcyclobut[c]-isoquinolin-4(2H)-one and its (1 alpha, 2a beta, 8b beta)- isomer in 78 and 67% yields. The photolysis of the hypoiodite generated in situ from the (1 alpha, 2a alpha, 8b alpha)-(+/-)-cyclobutanol with mercury(II) oxide - iodine in benzene induced a regioselective beta-scission at the ring fusion bond of the cyclobutanoxyl radical to give 5-cyano-3,6-epoxy-3,4,5,6-tetrahydro-6-hydroxy-2-methyl-2- benzazocin-1(2H)-one in 76% yield. The cyano substituent and the amide nitrogen play a decisive role in directing the bond to be cleaved.

  DOI：

  10.3987/com-93-s94
• 作为产物：
  描述：

  4-羟基-1(2H)-异喹啉酮 在 吡啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.75h， 生成 4-benzyloxycarbonyloxy-2-methyl-1(2H)-isoquinolinone
  参考文献：
  名称：

  Photoinduced Molecular Transformations. part 147. [2+2]Photoaddition of Protected 4-Hydroxy-1(2H)-isoquinolinone with an Electrondeficient Alkene and the Formation of a 3,6-Epoxy-3,4,5,6-tetrahydro-2-benzazocin-1(2H)-one via a b-Scission of Cyclobutanoxyl Radicals Generated from the Resulting photoadduct

  摘要：

  The direct irradiation of 4-benzyloxycarbonyloxy-2-methyl-1(2H)-isoquinolinone gave a 1 to 1 ratio of two stereoisomers of [2+2] photoadducts in 97% yield. Removal of the protecting group from the adducts by hydrogenolysis gave the corresponding cyclobutanols, (1 alpha, 2a alpha, 8b alpha)-(+/-)-1-cyano-1,2a,3,8b-tetrahydro-8 b-hydroxy-3 -methylcyclobut[c]-isoquinolin-4(2H)-one and its (1 alpha, 2a beta, 8b beta)- isomer in 78 and 67% yields. The photolysis of the hypoiodite generated in situ from the (1 alpha, 2a alpha, 8b alpha)-(+/-)-cyclobutanol with mercury(II) oxide - iodine in benzene induced a regioselective beta-scission at the ring fusion bond of the cyclobutanoxyl radical to give 5-cyano-3,6-epoxy-3,4,5,6-tetrahydro-6-hydroxy-2-methyl-2- benzazocin-1(2H)-one in 76% yield. The cyano substituent and the amide nitrogen play a decisive role in directing the bond to be cleaved.

  DOI：

  10.3987/com-93-s94