12-(3-Chlorophenyl)-5,7,8,9,10,12-hexahydro-5,6-dihydroxypyrido<2,3-b>azecin-11(6H)-one | 138963-12-9

• 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: 12-(3-Chlorophenyl)-5,7,8,9,10,12-hexahydro-5,6-dihydroxypyrido<2,3-b>azecin-11(6H)-one
• CAS: 138963-12-9；139066-47-0
• 化学式: C₁₈H₁₉ClN₂O₃
• 分子量: 346.813
• InChiKey: AFUSUYNPTFPZNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.66
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  12-(3-Chlorophenyl)-5,7,8,9,10,12-hexahydro-5,6-dihydroxypyrido<2,3-b>azecin-11(6H)-one 、 N,N'-羰基二咪唑 以 二氯甲烷 为溶剂， 反应 3.0h， 以44%的产率得到9-(3-Chlorophenyl)-3a,4,5,6,7,13b-hexahydro-2H-1,3-dioxolo<4,5-d>pyrido<2,3-b>azecin-2,8(9H)-dione
  参考文献：
  名称：

  Oxidative cleavage of a tricyclic pyridone to a bicyclic lactam-dione

  摘要：

  Two equivalents of anhydrous m-chloroperbenzoic acid (m-CPBA) cleaved the pyridone ring of 10-(3-chlorophenyl)-6,8,9,10-tetrahydrobenzo[b][1,8]naphthyridin-5(7H)-one, forming the ten-membered lactam alpha-diketone 12-(3-chlorophenyl)-7,8,9,10-tetrahydropyrido[2,3-b]azecine-5,6,11(12H)-trione. Under aqueous conditions, one equivalent of m-CPBA and the same pyridone formed the lactam alpha-ketol 12-(3-chlorophenyl)-7,8,9,10-tetrahydro-6-hydroxypyrido[2,3-b]azecine-5,11(6H, 12H)-dione, which partly confirmed the postulated mechanism of ring cleavage.

  DOI：

  10.1016/s0040-4020(01)96046-6
• 作为产物：
  描述：

  12-(3-Chlorophenyl)-7,8,9,10-tetrahydropyrido<2,3-b>azecine-5,6,11(12H)-trione 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以34%的产率得到12-(3-Chlorophenyl)-5,7,8,9,10,12-hexahydro-5,6-dihydroxypyrido<2,3-b>azecin-11(6H)-one
  参考文献：
  名称：

  Oxidative cleavage of a tricyclic pyridone to a bicyclic lactam-dione

  摘要：

  Two equivalents of anhydrous m-chloroperbenzoic acid (m-CPBA) cleaved the pyridone ring of 10-(3-chlorophenyl)-6,8,9,10-tetrahydrobenzo[b][1,8]naphthyridin-5(7H)-one, forming the ten-membered lactam alpha-diketone 12-(3-chlorophenyl)-7,8,9,10-tetrahydropyrido[2,3-b]azecine-5,6,11(12H)-trione. Under aqueous conditions, one equivalent of m-CPBA and the same pyridone formed the lactam alpha-ketol 12-(3-chlorophenyl)-7,8,9,10-tetrahydro-6-hydroxypyrido[2,3-b]azecine-5,11(6H, 12H)-dione, which partly confirmed the postulated mechanism of ring cleavage.

  DOI：

  10.1016/s0040-4020(01)96046-6

文献信息

• Oxidative cleavage of a tricyclic pyridone to a bicyclic lactam-dione
  作者：Richard J. Friary、John H. Schwerdt

  DOI：10.1016/s0040-4020(01)96046-6

  日期：1991.1

  Two equivalents of anhydrous m-chloroperbenzoic acid (m-CPBA) cleaved the pyridone ring of 10-(3-chlorophenyl)-6,8,9,10-tetrahydrobenzo[b][1,8]naphthyridin-5(7H)-one, forming the ten-membered lactam alpha-diketone 12-(3-chlorophenyl)-7,8,9,10-tetrahydropyrido[2,3-b]azecine-5,6,11(12H)-trione. Under aqueous conditions, one equivalent of m-CPBA and the same pyridone formed the lactam alpha-ketol 12-(3-chlorophenyl)-7,8,9,10-tetrahydro-6-hydroxypyrido[2,3-b]azecine-5,11(6H, 12H)-dione, which partly confirmed the postulated mechanism of ring cleavage.