(8R*,14S*)-(+/-)-8-hydroxymethyltetrahydropalmatine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: (8R*,14S*)-(+/-)-8-hydroxymethyltetrahydropalmatine
• 英文别名: [(8R,13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-8-yl]methanol
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: QFMVLHJHJAMXIF-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  四氢罂粟碱盐酸盐 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 5.0h， 生成 (8R*,14S*)-(+/-)-8-hydroxymethyltetrahydropalmatine
  参考文献：
  名称：

  （-）-水榄红碱的结构和全合成。藜角藜的一种不寻常的原小pro碱生物碱

  摘要：

  对Ceratocapnos heterocarpa（Papaveraceae）中存在的生物碱的检查导致分离出了新的原小ber碱生物碱（-）-马拉西茶碱。该生物碱的特征结构特征是1,2,10,11取代模式和C-8处的羟甲基。已经开发了由苄基异喹啉（±）-去甲福西林合成（±）-马拉金嘌呤及其C-8差向异构体的方法。报道了几种C-8取代的原小ine碱生物碱的光谱数据（pmr，cmr和ir）与喹oli嗪构象有关。

  DOI：

  10.1016/s0040-4020(01)86777-6

文献信息

• Photochemical hydroxymethylation of protoberberine alkaloids. Total synthesis of (±)-solidaline
  作者：Rafael Suau、Francisco Nájera、Rodrigo Rico

  DOI：10.1016/0040-4039(96)00625-9

  日期：1996.5

  berberinium salts was readily achieved by photoaddition of methanol. The resulting photoproducts were isolated as tetrahydroprotoberberine derivatives. By combining this photochemical reaction with the oxidation of the photoproduct, the synthesis of (±)-solidaline starting from palmatine chloride was accomplished for the first time.

  通过甲醇的光加成很容易地在小salts盐的C-8位上引入羟甲基。分离得到的光产物为四氢小ber碱衍生物。通过将该光化学反应与光产物的氧化相结合，首次完成了从氯化棕榈酰开始的（±）-固醇的合成。
• Hydroxymethylation of protoberberine alkaloids by photoinduced SET. The total synthesis of (±)-solidaline
  作者：Rafael Suau、Francisco Nájera、Rodrigo Rico

  DOI：10.1016/s0040-4020(99)00090-3

  日期：1999.3

  The direct insertion of a hydroxymethyl group at position C-8 in a protoberberinium ion by photoaddition of methanol was approached via two mechanistic pathways: acetone-sensitized and single-electron transfer. The latter produces 8-hydroxymethylberbines in good yields after reduction. By combining this photochemical reaction with the oxidation of the photoproduct, syntheses of (+/-)-solidaline and its C-13 epimer from palmatine chloride were accomplished for the first time. On the other hand, insertion of a hydroxymethyl group at position 14 of the berberine skeleton in order to open a synthetic pathway for zijinlongine proved unsuccessful. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Structure and total synthesis of (-)-malacitanine. An unusual protoberberine alkaloid from ceratocapnos heterocarpa
  作者：Rafael Suau、M. Victoria Silva、Maria Valpuesta

  DOI：10.1016/s0040-4020(01)86777-6

  日期：——

  The examination of the alkaloids present in Ceratocapnos heterocarpa (Papaveraceae) had led to the isolation of the new protoberberine alkaloid, (-)-malacitanine. Characteristic structural features for this alkaloid are the 1,2,10,11-substitution pattern and the hydroxymethyl group at C-8. The synthesis of (±)-malacitanine and its C-8 epimer from the benzylisoquinoline (±)-norcrassifoline has been

  对Ceratocapnos heterocarpa（Papaveraceae）中存在的生物碱的检查导致分离出了新的原小ber碱生物碱（-）-马拉西茶碱。该生物碱的特征结构特征是1,2,10,11取代模式和C-8处的羟甲基。已经开发了由苄基异喹啉（±）-去甲福西林合成（±）-马拉金嘌呤及其C-8差向异构体的方法。报道了几种C-8取代的原小ine碱生物碱的光谱数据（pmr，cmr和ir）与喹oli嗪构象有关。