2-氨基-7-氟-9H-芴-9-醇 | 88899-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 2-氨基-7-氟-9H-芴-9-醇
• 中文别名: 2,2'-[(3,3'-二甲基[1,1'-联苯基]-4,4'-二基)二[亚氨基[1-(1-羟基亚乙基)-2-羰基-2,1-乙二基]偶氮]]二[5-[[[(4-磺酸根苯基)氨基]羰基]氨基]苯酸]四钠
• 英文名称: (+/-)-solanapyrone B
• 英文别名: Solanapyrone B；6-[(1R,2S,4aR,8aR)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-(hydroxymethyl)-4-methoxypyran-2-one
• CAS: 88899-60-9
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: YJHFAFJKTXEFDR-SFDCBXKLSA-N

物化性质

• 沸点：
  500.6±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基-7-氟-9H-芴-9-醇 在 potassium phosphate buffer 、 enzyme from A_. solani 、 甘油 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-甲氧基-6-[(1R,2S,4aR,8aR)-2-甲基-1,2,4a,5,6,7,8,8a-八氢-1-萘基]-2-氧代-2H-吡喃-3-甲醛
  参考文献：
  名称：

  Total Synthesis of (−)-Solanapyrone A via Enzymatic Diels−Alder Reaction of Prosolanapyrone

  摘要：

  The syntheses of prosolanapyrones I (6) and II (7) via the aldol reactions of pyrone and dienal segments have been achieved in five steps in 31% overall yield for 6 and seven steps in 5% overall yield for 7. An improved synthetic route starting from vinylpyrone 27 provided 7 in 11 steps in 12% overall yield. The enzymatic Diels-Alder reaction of 7 affords (-)-solanapyrone A (1) with high enantioselectivity and with good exo-selectivity, which is difficult to attain by chemical methods. In addition, a crude enzyme preparation from Alternaria solani has been used to perform a kinetic resolution of(+/-)-3.

  DOI：

  10.1021/jo980743r
• 作为产物：
  描述：

  4-甲氧基-6-甲基-2H-吡喃酮 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四丁基氟化铵 、 四氯化钛 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 对甲苯磺酰氯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 35.0h， 生成 2-氨基-7-氟-9H-芴-9-醇
  参考文献：
  名称：

  Total Synthesis of (−)-Solanapyrone A via Enzymatic Diels−Alder Reaction of Prosolanapyrone

  摘要：

  The syntheses of prosolanapyrones I (6) and II (7) via the aldol reactions of pyrone and dienal segments have been achieved in five steps in 31% overall yield for 6 and seven steps in 5% overall yield for 7. An improved synthetic route starting from vinylpyrone 27 provided 7 in 11 steps in 12% overall yield. The enzymatic Diels-Alder reaction of 7 affords (-)-solanapyrone A (1) with high enantioselectivity and with good exo-selectivity, which is difficult to attain by chemical methods. In addition, a crude enzyme preparation from Alternaria solani has been used to perform a kinetic resolution of(+/-)-3.

  DOI：

  10.1021/jo980743r

文献信息

• Synthesis of (±)-solanapyrones A and B
  作者：Barry Lygo、Mohamed Bhatia、Jason W.B. Cooke、David J. Hirst

  DOI：10.1016/s0040-4039(03)00288-0

  日期：2003.3

  In this paper we report the development of a stereoselective IMDA approach to the phytotoxic polyketides (+/-)-solanapyrones A and B. The stereoselectivity of the key IMDA cycloaddition was optimized by investigating a range of 2,8,10-dodecatrienoic acid derivatives. This established that use of the Weinreb amide led to the desired exo-selectivity and also facilitated construction of the pyrone moiety. A novel approach to the installation of the C-3 formyl group in solanapyrone A is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Total Synthesis of (−)-Solanapyrone A via Enzymatic Diels−Alder Reaction of Prosolanapyrone
  作者：Hideaki Oikawa、Tomonori Kobayashi、Kinya Katayama、Yuichi Suzuki、Akitami Ichihara

  DOI：10.1021/jo980743r

  日期：1998.11.1

  The syntheses of prosolanapyrones I (6) and II (7) via the aldol reactions of pyrone and dienal segments have been achieved in five steps in 31% overall yield for 6 and seven steps in 5% overall yield for 7. An improved synthetic route starting from vinylpyrone 27 provided 7 in 11 steps in 12% overall yield. The enzymatic Diels-Alder reaction of 7 affords (-)-solanapyrone A (1) with high enantioselectivity and with good exo-selectivity, which is difficult to attain by chemical methods. In addition, a crude enzyme preparation from Alternaria solani has been used to perform a kinetic resolution of(+/-)-3.