methyl (3R,4R)-4-(1-hydroxy-4,5,6-trimethoxynaphthalen-2-yl)-3,4-isopropylidenedioxybutanoate | 1526958-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl (3R,4R)-4-(1-hydroxy-4,5,6-trimethoxynaphthalen-2-yl)-3,4-isopropylidenedioxybutanoate
• 英文别名: methyl 2-[(4R,5R)-5-(1-hydroxy-4,5,6-trimethoxynaphthalen-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl]acetate
• CAS: 1526958-31-5
• 化学式: C₂₁H₂₆O₈
• 分子量: 406.433
• InChiKey: NIJPBOQRNSSBOS-DNVCBOLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (3R,4R)-4-(1-hydroxy-4,5,6-trimethoxynaphthalen-2-yl)-3,4-isopropylidenedioxybutanoate 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.33h， 以85%的产率得到methyl (3R,4R)-4-(1,4,5,6-tetramethoxynaphthalen-2-yl)-3,4-isopropylidenedioxybutanoate
  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：

  1-溴-2,3-二甲氧基苯 在 正丁基锂 作用下， 以 正己烷 、 Petroleum ether 、 苯 为溶剂， 反应 17.25h， 生成 methyl (3R,4R)-4-(1-hydroxy-4,5,6-trimethoxynaphthalen-2-yl)-3,4-isopropylidenedioxybutanoate
  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.