N-(乙酰氧基)-N-((4-甲基苯基)甲氧基)苯酰胺 | 108890-89-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异色满醌
• 中文名称: N-(乙酰氧基)-N-((4-甲基苯基)甲氧基)苯酰胺
• 中文别名: (3aR-(3aalpha,5alpha,11balpha))-3,3a,5,11b-四氢-7-羟基-8-甲氧基-5-甲基-2H-呋喃并(3,2-b)萘并(2,3-d)吡喃-2,6,11-三酮
• 英文名称: arizonin B1
• 英文别名: (11R,15R,17R)-4-hydroxy-5-methoxy-17-methyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione
• CAS: 108890-89-7
• 化学式: C₁₇H₁₄O₇
• 分子量: 330.294
• InChiKey: CLXIMNXZNQOXNS-WEWYWXMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(乙酰氧基)-N-((4-甲基苯基)甲氧基)苯酰胺 、 碘甲烷 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以77%的产率得到arizonin C1
  参考文献：
  名称：

  A concise total synthesis of arizonins B1 and C1

  摘要：

  A concise and efficient total synthesis of arizonins B1 and C1 is reported. A key building block alkyne is synthesized from a-glucono-S-lactone and used in the Dotz benzannulation reaction to construct the naphthalene unit. An oxa-Pictet-Spengler reaction gave the pyran ring while an H2SO4 mediated isomerization set the correct stereochemistry of the target molecules. Alternatively, a direct anti-pyran stereochemistry was prepared in a TFA solvent. The synthesis is competitive to previous reports and marks the first enantioselective synthesis of arizonin B1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.10.011
• 作为产物：
  描述：

  在 硫酸 作用下， 反应 0.75h， 以48%的产率得到N-(乙酰氧基)-N-((4-甲基苯基)甲氧基)苯酰胺
  参考文献：
  名称：

  A concise total synthesis of arizonins B1 and C1

  摘要：

  A concise and efficient total synthesis of arizonins B1 and C1 is reported. A key building block alkyne is synthesized from a-glucono-S-lactone and used in the Dotz benzannulation reaction to construct the naphthalene unit. An oxa-Pictet-Spengler reaction gave the pyran ring while an H2SO4 mediated isomerization set the correct stereochemistry of the target molecules. Alternatively, a direct anti-pyran stereochemistry was prepared in a TFA solvent. The synthesis is competitive to previous reports and marks the first enantioselective synthesis of arizonin B1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.10.011

文献信息

• A concise total synthesis of arizonins B1 and C1
  作者：Rodney A. Fernandes、Sandip V. Mulay、Vijay P. Chavan

  DOI：10.1016/j.tetasy.2013.10.011

  日期：2013.12

  A concise and efficient total synthesis of arizonins B1 and C1 is reported. A key building block alkyne is synthesized from a-glucono-S-lactone and used in the Dotz benzannulation reaction to construct the naphthalene unit. An oxa-Pictet-Spengler reaction gave the pyran ring while an H2SO4 mediated isomerization set the correct stereochemistry of the target molecules. Alternatively, a direct anti-pyran stereochemistry was prepared in a TFA solvent. The synthesis is competitive to previous reports and marks the first enantioselective synthesis of arizonin B1. (C) 2013 Elsevier Ltd. All rights reserved.