1-allyl-2-(benzylamino)-4-<<(tert-butyloxy)carbonyl>oxy>naphthalene | 143144-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-allyl-2-(benzylamino)-4-<<(tert-butyloxy)carbonyl>oxy>naphthalene
• 英文别名: [3-(Benzylamino)-4-prop-2-enylnaphthalen-1-yl] tert-butyl carbonate
• CAS: 143144-68-7
• 化学式: C₂₅H₂₇NO₃
• 分子量: 389.494
• InChiKey: XSFOZOHDICWXJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-allyl-2-(benzylamino)-4-<<(tert-butyloxy)carbonyl>oxy>naphthalene 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 四氧化锇 、 甲酸 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 38.0h， 生成
  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：

  2-benzylamino-[1,4]naphthoquinone 在 4-二甲氨基吡啶 、 sodium dithionite 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 43.0h， 生成 1-allyl-2-(benzylamino)-4-<<(tert-butyloxy)carbonyl>oxy>naphthalene
  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

• Reductive aromatization of quinols. New convenient methods for the regiospecific synthesis of p-hydroxy C-aryl glycals
  作者：Kathlyn A. Parker、Craig A. Coburn、Paul D. Johnson、Paul Aristoff

  DOI：10.1021/jo00046a049

  日期：1992.9
• 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.