(2S)-1,2-dihydroxy-3-<2-(benzylamino)-4-<<(tert-butyloxy)carbonyl>oxy>naphthalene-1-yl>propane | 144299-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S)-1,2-dihydroxy-3-<2-(benzylamino)-4-<<(tert-butyloxy)carbonyl>oxy>naphthalene-1-yl>propane
• 英文别名: (2S)-1,2-dihydroxy-3-(2-(benzylamino)-4-{[(tert-butyloxy)carbonyl]oxy}naphthalene-1-yl)propane；[3-(benzylamino)-4-[(2S)-2,3-dihydroxypropyl]naphthalen-1-yl] tert-butyl carbonate
• CAS: 144299-23-0
• 化学式: C₂₅H₂₉NO₅
• 分子量: 423.509
• InChiKey: DSNZYRSEVVYTSK-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二碳酸二叔丁酯 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 水 、 叔丁醇 为溶剂， 反应 60.0h， 生成 (2S)-1,2-dihydroxy-3-<2-(benzylamino)-4-<<(tert-butyloxy)carbonyl>oxy>naphthalene-1-yl>propane
  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.