(4S)-7,8-dimethoxy-2,4-dimethyl-4,5-dihydronaphtho-[1,2-d][1,3]dioxepine | 1078723-17-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4S)-7,8-dimethoxy-2,4-dimethyl-4,5-dihydronaphtho-[1,2-d][1,3]dioxepine
• 英文别名: (4S)-7,8-dimethoxy-2,4-dimethyl-4,5-dihydrobenzo[i][1,3]benzodioxepine
• CAS: 1078723-17-7
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: AXYHXVJXASRXLF-VUWPPUDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-7,8-dimethoxy-2,4-dimethyl-4,5-dihydronaphtho-[1,2-d][1,3]dioxepine 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以83%的产率得到(S)-(+)-2-(2'-hydroxypropyl)-5-methoxy-1,4-naphthoquinone
  参考文献：
  名称：

  A short enantioselective synthesis of (+)-eleutherin, (+)-allo-eleutherin and a formal synthesis of (+)-nocardione B

  摘要：

  A short enantioselective synthesis of (+)-eleutherin, (+)-allo-eleutherin and the formal synthesis of (+)-nocardione B is described. The synthesis is completed in six steps in overall yields of 8% for eleutherin and 14% for allo-eleutherin. The synthetic strategy features ail efficient combination of the Dotz annulation reaction with a chiral alkyne and an oxa-Pictet Spengler reaction as the keys steps in the stereodivergent synthesis of (+)-eleutherin and (+)-allo-eleutherin. The synthesis of (S)-(+)-2-(2'-hydroxypropyl)-5-methoxy-1,4-naphthoquinone entails the formal synthesis of (+)-nocardione B. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.065
• 作为产物：
  描述：

  (2S)-2-(2-(tert-butyldimethylsilyloxy)propyl)-4,5-dimethoxynaphthalen-1-ol 在 三氟化硼乙醚 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 14.5h， 生成 (4S)-7,8-dimethoxy-2,4-dimethyl-4,5-dihydronaphtho-[1,2-d][1,3]dioxepine
  参考文献：
  名称：

  A concise and improved synthesis of (+)-eleutherin, (+)-allo-eleutherin and a formal synthesis of (+)-nocardione B

  摘要：

  A concise and improved stereoselective synthesis of (+)-eleutherin, (+)-allo-eleutherin and the formal synthesis of (+)-nocardione B is described. The synthesis is based on a Dotz benzannulation and an improved oxa-Pictet-Spengler cyclization as the key steps. The synthesis is achieved in six steps in overall yields of 18% for eleutherin and 20% for allo-eleutherin. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.011

文献信息

• A short enantioselective synthesis of (+)-eleutherin, (+)-allo-eleutherin and a formal synthesis of (+)-nocardione B
  作者：Rodney A. Fernandes、Vijay P. Chavan、Arun B. Ingle

  DOI：10.1016/j.tetlet.2008.08.065

  日期：2008.10

  A short enantioselective synthesis of (+)-eleutherin, (+)-allo-eleutherin and the formal synthesis of (+)-nocardione B is described. The synthesis is completed in six steps in overall yields of 8% for eleutherin and 14% for allo-eleutherin. The synthetic strategy features ail efficient combination of the Dotz annulation reaction with a chiral alkyne and an oxa-Pictet Spengler reaction as the keys steps in the stereodivergent synthesis of (+)-eleutherin and (+)-allo-eleutherin. The synthesis of (S)-(+)-2-(2'-hydroxypropyl)-5-methoxy-1,4-naphthoquinone entails the formal synthesis of (+)-nocardione B. (c) 2008 Elsevier Ltd. All rights reserved.
• A concise and improved synthesis of (+)-eleutherin, (+)-allo-eleutherin and a formal synthesis of (+)-nocardione B
  作者：Rodney A. Fernandes、Vijay P. Chavan、Sandip V. Mulay

  DOI：10.1016/j.tetasy.2011.02.011

  日期：2011.2

  A concise and improved stereoselective synthesis of (+)-eleutherin, (+)-allo-eleutherin and the formal synthesis of (+)-nocardione B is described. The synthesis is based on a Dotz benzannulation and an improved oxa-Pictet-Spengler cyclization as the key steps. The synthesis is achieved in six steps in overall yields of 18% for eleutherin and 20% for allo-eleutherin. (C) 2011 Elsevier Ltd. All rights reserved.