3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydro-4H-benzoquinoline | 144191-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydro-4H-benzoquinoline
• 英文别名: (4-acetyl-2-hydroxy-2,3-dihydro-1H-benzo[f]quinolin-6-yl) tert-butyl carbonate
• CAS: 144191-98-0
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: JPHZCYLITSZDBI-UHFFFAOYSA-N

物化性质

• 沸点：
  605.4±55.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydro-4H-benzoquinoline 在 4-二甲氨基吡啶 、 sodium hydride 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one
  参考文献：
  名称：

  Synthesis of CBI-PDE-I-dimer, the benzannelated analog of CC-1065

  摘要：

  A practical synthesis of CBI (2), utilizing inexpensive starting materials, was developed and applied to the synthesis of benzannelated analogs of CC-1065, in particular CBI-PDE-I-dimer (13) and CBI-bis-indole (17). While a Sharpless asymmetric dihydroxylation reaction proved effective at providing optically active intermediates, a more classical resolution procedure was used to prepare materials of higher optical purity. A novel cyclization employing a six-membered-ring intermediate (12) was employed to construct the cyclopropyl ring in CBI. Like CC-1065, CBI-PDE-I-dimer appears to cause delayed toxicity in mice.

  DOI：

  10.1021/jo00049a035
• 作为产物：
  描述：

  [3-amino-4-(2,3-dihydroxypropyl)naphthalen-1-yl] tert-butyl carbonate 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.5h， 生成 3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydro-4H-benzoquinoline
  参考文献：
  名称：

  Synthesis of CBI-PDE-I-dimer, the benzannelated analog of CC-1065

  摘要：

  A practical synthesis of CBI (2), utilizing inexpensive starting materials, was developed and applied to the synthesis of benzannelated analogs of CC-1065, in particular CBI-PDE-I-dimer (13) and CBI-bis-indole (17). While a Sharpless asymmetric dihydroxylation reaction proved effective at providing optically active intermediates, a more classical resolution procedure was used to prepare materials of higher optical purity. A novel cyclization employing a six-membered-ring intermediate (12) was employed to construct the cyclopropyl ring in CBI. Like CC-1065, CBI-PDE-I-dimer appears to cause delayed toxicity in mice.

  DOI：

  10.1021/jo00049a035

文献信息

• Synthesis of CBI-PDE-I-dimer, the benzannelated analog of CC-1065
  作者：Paul A. Aristoff、Paul D. Johnson

  DOI：10.1021/jo00049a035

  日期：1992.11

  A practical synthesis of CBI (2), utilizing inexpensive starting materials, was developed and applied to the synthesis of benzannelated analogs of CC-1065, in particular CBI-PDE-I-dimer (13) and CBI-bis-indole (17). While a Sharpless asymmetric dihydroxylation reaction proved effective at providing optically active intermediates, a more classical resolution procedure was used to prepare materials of higher optical purity. A novel cyclization employing a six-membered-ring intermediate (12) was employed to construct the cyclopropyl ring in CBI. Like CC-1065, CBI-PDE-I-dimer appears to cause delayed toxicity in mice.