(S)-(+)-2-(2'-hydroxypropyl)-5-methoxy-1,4-naphthalenediol | 394738-49-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-(+)-2-(2'-hydroxypropyl)-5-methoxy-1,4-naphthalenediol
• 英文别名: (2S)-2-(2-hydroxypropyl)-5-methoxynaphthalene-1,4-diol；2-[(2S)-2-hydroxypropyl]-5-methoxynaphthalene-1,4-diol
• CAS: 394738-49-9
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: NNYNFNBIUMCTSZ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-(2'-hydroxypropyl)-5-methoxy-1,4-naphthalenediol 在 benzeneselenenic anhydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 19.5h， 生成 (R)-nocardione B
  参考文献：
  名称：

  Synthesis and Absolute Configuration of Nocardione A and B, Furano-o-naphthoquinone-Type Metabolites of Nocardia sp. with Antifungal, Cytotoxic, and Enzyme Inhibitory Activities

  摘要：

  (±)-Nocardione A (1), (S)-(-)-nocardione A 和 (R)-(+)-nocardione B (2) 通过以丙二醇环氧丙烷和 5-苄氧基（或甲氧基）-1-四氢萘酮的对映体为起始原料进行合成。天然存在的 (-)-1 和 (-)-2 的绝对构型均被确定为 (S)。

  DOI：

  10.1002/1099-0690(200111)2001:22<4313::aid-ejoc4313>3.0.co;2-j
• 作为产物：
  描述：

  (4S)-7,8-dimethoxy-2,4-dimethyl-4,5-dihydronaphtho-[1,2-d][1,3]dioxepine 在 sodium dithionite 、 ammonium cerium (IV) nitrate 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 (S)-(+)-2-(2'-hydroxypropyl)-5-methoxy-1,4-naphthalenediol
  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 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.
• Synthesis and Absolute Configuration of Nocardione A and B, Furano-o-naphthoquinone-Type Metabolites of Nocardia sp. with Antifungal, Cytotoxic, and Enzyme Inhibitory Activities
  作者：Yoshihisa Tanada、Kenji Mori

  DOI：10.1002/1099-0690(200111)2001:22<4313::aid-ejoc4313>3.0.co;2-j

  日期：2001.11

  (+/-)-Nocardione A (1), (S)-(-)-nocardione A, and (R)-(+)-nocardione B (2) were synthesized by starting from the enantiomers of propylene oxide and 5-benzyloxy (or methoxy)-1-tetralone. The absolute configurations of the naturally occurring (-)-1 and (-)-2 were established as (S).

  (±)-Nocardione A (1), (S)-(-)-nocardione A 和 (R)-(+)-nocardione B (2) 通过以丙二醇环氧丙烷和 5-苄氧基（或甲氧基）-1-四氢萘酮的对映体为起始原料进行合成。天然存在的 (-)-1 和 (-)-2 的绝对构型均被确定为 (S)。