[3-(benzylideneamino)-4-[(2S)-2,3-dihydroxypropyl]naphthalen-1-yl] tert-butyl carbonate | 144192-04-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [3-(benzylideneamino)-4-[(2S)-2,3-dihydroxypropyl]naphthalen-1-yl] tert-butyl carbonate
• CAS: 144192-04-1
• 化学式: C₂₅H₂₇NO₅
• 分子量: 421.493
• InChiKey: BUCSBLFQWOJZJY-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  88.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-benzylamino-[1,4]naphthoquinone 在 4-二甲氨基吡啶 、 四氧化锇 、 sodium dithionite 、 hydroquinuclidine 9-phenanthryl ether 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 乙醚 、 水 、 叔丁醇 为溶剂， 反应 61.0h， 生成 [3-(benzylideneamino)-4-[(2S)-2,3-dihydroxypropyl]naphthalen-1-yl] tert-butyl carbonate
  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.