(-)-Shinjulactone H | 4283-48-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-Shinjulactone H
• 英文别名: shinjulactone H；Amarolide；(1S,2S,4S,6R,7S,9R,13S,14R,15S,17S)-4,15-dihydroxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.02,7.013,17]heptadecane-3,11,16-trione
• CAS: 4283-48-1
• 化学式: C₂₀H₂₈O₆
• 分子量: 364.439
• InChiKey: HSTCACQRSLZQHZ-GZPFNNFFSA-N

物化性质

• 沸点：
  579.4±50.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-Shinjulactone H 、 乙酸酐 以 吡啶 为溶剂， 以12 mg的产率得到2,12-di-O-acetylshinjulactone H
  参考文献：
  名称：

  Shinjulactones G and H, New Bitter Principles ofAilanthus altissimaSWINGLE

  摘要：

  从臭椿（Ailanthus altissima Swingle）中分离出两种苦味的藜芦苷，即shinjulactones G和H，并通过光谱和化学方法确定其结构分别为1β,11β,12α,20-tetrahydroxypicras-3-ene-2,16-dione和2α,12β-dihydroxypicrasane-1,11,16-trione。

  DOI：

  10.1246/bcsj.57.2013
• 作为产物：
  描述：

  Isopicrasin B 在 platinum(IV) oxide 15-冠醚-5 、 氢气 、 三溴化硼 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 18.5h， 生成 (-)-Shinjulactone H
  参考文献：
  名称：

  A partial synthesis of (-)-shinjulactone H from (+)-quassin

  摘要：

  A partial synthesis of (-)-shinjulactone H (3) from (+)-quassin (1) required the selective manipulation of two similar O-methyldiosphenol groups. Protection of the delta-lactone in 1 as an ortho ester, selective reduction of the C-1 carbonyl group, hydrolysis of the resulting enol ether in the A ring, and catalytic hydrogenation of the O-methyldiosphenol in the C ring delivered an intermediate possessing an alpha-ketol group in the A ring and an alpha-methoxy ketone group in the C ring. Demethylation and concomitant alpha-ketol tautomerization in the A ring delivered (-)-shinjulactone H (3).

  DOI：

  10.1021/jo00034a008

文献信息

• Niimi, Yoshio; Tsuyuki, Takahiko; Takahashi, Takeyoshi, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 10, p. 4302 - 4306
  作者：Niimi, Yoshio、Tsuyuki, Takahiko、Takahashi, Takeyoshi、Matsushita, Kazuhiro

  DOI：——

  日期：——
• HIROTA, HIROSHI;YOKOYAMA, AKIHISA;MIYAJI, KATSUAKI;NAKAMURA, TOSHIO;IGARA+, J. ORG. CHEM., 56,(1991) N, C. 1119-1127
  作者：HIROTA, HIROSHI、YOKOYAMA, AKIHISA、MIYAJI, KATSUAKI、NAKAMURA, TOSHIO、IGARA+

  DOI：——

  日期：——
• A partial synthesis of (-)-shinjulactone H from (+)-quassin
  作者：Hideo Nakamura、Sundar Vasudevan、Moonsun Kim、Carolyn P. Brock、David S. Watt

  DOI：10.1021/jo00034a008

  日期：1992.4

  A partial synthesis of (-)-shinjulactone H (3) from (+)-quassin (1) required the selective manipulation of two similar O-methyldiosphenol groups. Protection of the delta-lactone in 1 as an ortho ester, selective reduction of the C-1 carbonyl group, hydrolysis of the resulting enol ether in the A ring, and catalytic hydrogenation of the O-methyldiosphenol in the C ring delivered an intermediate possessing an alpha-ketol group in the A ring and an alpha-methoxy ketone group in the C ring. Demethylation and concomitant alpha-ketol tautomerization in the A ring delivered (-)-shinjulactone H (3).
• Shinjulactones G and H, New Bitter Principles of<i>Ailanthus altissima</i>SWINGLE
  作者：Masami Ishibashi、Shin Yoshimura、Takahiko Tsuyuki、Takeyoshi Takahashi、Kazuhiro Matsushita

  DOI：10.1246/bcsj.57.2013

  日期：1984.7

  Two bitter quassinoids, shinjulactones G and H were isolated from Ailanthus altissima  Swingle and their structures were determined to be 1β,11β,12α,20-tetrahydroxypicras-3-ene-2,16-dione and 2α,12β-dihydroxypicrasane-1,11,16-trione, respectively, by spectral and chemical means.

  从臭椿（Ailanthus altissima Swingle）中分离出两种苦味的藜芦苷，即shinjulactones G和H，并通过光谱和化学方法确定其结构分别为1β,11β,12α,20-tetrahydroxypicras-3-ene-2,16-dione和2α,12β-dihydroxypicrasane-1,11,16-trione。