(2R,3R)-5,8-dimethoxy-3-methyl-2-propylamino-1,2,3,4-tetrahydronaphthalene | 496043-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (2R,3R)-5,8-dimethoxy-3-methyl-2-propylamino-1,2,3,4-tetrahydronaphthalene
• CAS: 496043-15-3
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: RPEIKZDEROJHBY-BXUZGUMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  30.49
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-5,8-dimethoxy-3-methyl-2-propylamino-1,2,3,4-tetrahydronaphthalene 在 氢溴酸 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 5,8-dihydroxy-3R-methyl-2R-dipropylamino-1,2,3,4-tetrahydronaphthalene hydrobromide
  参考文献：
  名称：

  Synthesis of (−)-5,8-Dihydroxy-3R-methyl-2R-(dipropylamino)-1,2,3,4-tetrahydronaphthalene: An Inhibitor of β-Amyloid1–42 Aggregation

  摘要：

  A concise synthesis of the beta-amyloid(1-42) aggregation inhibitor (-)-5,8-dihydroxy-3R-methyl-2R-(dipropylamino)-1,2,3,4-tetrahydronaphthalene [(-)-2] has been developed. The key step is a regio- and diastereoselective hydroboration-amination sequence to convert alkene 6 into amine 9. Enantiomeric resolution was achieved by recrystallization of amine 9 as the dibenzoyl-D-tartaric acid salt. Hydroquinone 2 is a potent inhibitor of the fibrillar aggregation of beta-amyloid as determined in two different assay systems. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00251-1
• 作为产物：
  描述：

  对苯醌 、 alkaline earth salt of/the/ methylsulfuric acid 在 dichloroborane methyl sulfide complex 、 三氯化硼 作用下， 以 正己烷 、 正庚烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 56.0h， 生成 (2R,3R)-5,8-dimethoxy-3-methyl-2-propylamino-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Synthesis of (−)-5,8-Dihydroxy-3R-methyl-2R-(dipropylamino)-1,2,3,4-tetrahydronaphthalene: An Inhibitor of β-Amyloid1–42 Aggregation

  摘要：

  A concise synthesis of the beta-amyloid(1-42) aggregation inhibitor (-)-5,8-dihydroxy-3R-methyl-2R-(dipropylamino)-1,2,3,4-tetrahydronaphthalene [(-)-2] has been developed. The key step is a regio- and diastereoselective hydroboration-amination sequence to convert alkene 6 into amine 9. Enantiomeric resolution was achieved by recrystallization of amine 9 as the dibenzoyl-D-tartaric acid salt. Hydroquinone 2 is a potent inhibitor of the fibrillar aggregation of beta-amyloid as determined in two different assay systems. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00251-1