(+)-setoclavine | 519-12-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: (+)-setoclavine
• 英文别名: Setoclavin；Setoclavine；(6aR,9S)-7,9-dimethyl-4,6,6a,8-tetrahydroindolo[4,3-fg]quinolin-9-ol
• CAS: 519-12-0
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: BGVUWLLRNRBDAY-ZBFHGGJFSA-N

物化性质

• 熔点：
  216-222 °C (decomp)(Solv: ethyl ether (60-29-7))
• 沸点：
  473.6±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (+)-setoclavine 在 aluminum oxide 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以0.34 g的产率得到Lysergen
  参考文献：
  名称：

  Conversion of Agroclavine to Lysergol

  摘要：

  The conversion of agroclavine (1) to lysergol (4) has been achieved in three steps utilising the dehydration of setoclavine (2) to lysergene (3).

  DOI：

  10.1080/00397919208019288
• 作为产物：
  描述：

  曲麦角碱 在 potassium dichromate 、 硫酸 作用下， 生成 (+)-setoclavine
  参考文献：
  名称：

  Yamatodani; Abe, Journal of the Agricultural Chemical Society of Japan, 1955, vol. 19, p. 94

  摘要：

  DOI：

文献信息

• New Routes to Clavine-type Ergot Alkaloids. Part 1. First Total Synthesis of Three Natural Products: (+)-Setoclavine, (+)-Isosetoclavine, (-)-9,10-Dihydroisosetoclavine, and Structure Correction of the Latter
  作者：István Moldvai、Eszter Temesvári-Major、Eszter Gács-Baitz、Mária Incze、Gábor Dörnyei、Csaba Szántay

  DOI：10.3987/com-05-s(t)26

  日期：——

  The double bond in ring D of (+)-9,10-didehydro-6-methylergolin-8-one (2) was reduced selectively by catalytic hydrogenation to yield (-)-6-methylergolin-8-one (6). Grignard reaction of 6 has been performed with methylmagnesium iodide to afford two isomers (5 and 7). The main isomer having an 8 alpha-methyl group at C8 with a C/D-trans junction (5; (-)-dihydroisosetoclavine) proved to be identical with the natural product, hence its name and structure should be corrected. As a minor isomer (7) a C/D-cis clavine derivative was also isolated which can be regarded as unnatural (+)-8 alpha-hydroxy-costaclavine. (+)-Setoclavine (8) and (+)-isosetoclavine (9) have also been prepared from 2, thus achieving the first total synthesis of these natural products. Detailed structure elucidation of 5-9 has been carried out as well.
• Yamatodani; Abe, Journal of the Agricultural Chemical Society of Japan, 1955, vol. 19, p. 94
  作者：Yamatodani、Abe

  DOI：——

  日期：——
• Conversion of Agroclavine to Lysergol
  作者：J. R. Harris、D. C. Horwellt

  DOI：10.1080/00397919208019288

  日期：1992.4

  The conversion of agroclavine (1) to lysergol (4) has been achieved in three steps utilising the dehydration of setoclavine (2) to lysergene (3).