2,3-didehydropicrasin B | 26121-57-3

• 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: 2,3-didehydropicrasin B
• 英文别名: 2-hydroxy-12-methoxy-picrasa-2,12-diene-1,11,16-trione；2-Hydroxy-12-methoxy-picrasa-2,12-dien-1,11,16-trion；2-Desmethylquassin；(1S,2S,6S,7S,9R,13R,17S)-4-hydroxy-15-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.02,7.013,17]heptadeca-4,14-diene-3,11,16-trione
• CAS: 26121-57-3
• 化学式: C₂₁H₂₆O₆
• 分子量: 374.434
• InChiKey: IBDCZBYIEPTNQQ-CEAVDVEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-didehydropicrasin B 在 sodium hydride 、 碘甲烷 作用下， 生成 苦木素
  参考文献：
  名称：

  A partial synthesis of picrasin B and Δ2-picrasin B

  摘要：

  DOI：

  10.1016/s0040-4039(01)93834-1
• 作为产物：
  描述：

  Isopicrasin B 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以55%的产率得到2,3-didehydropicrasin B
  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

• Semisynthetic derivatives of quassin
  作者：Caroline C. Lang'at、Robert A. Watt、Istvan Toth、J.David Phillipson

  DOI：10.1016/s0040-4020(98)00367-6

  日期：1998.6

  The natural product quassin has been modified in order to produce compounds with potential antimalarial action. The modifications include demethylation, reduction of the keto function, esterification with simple organic acids and- to enhance the uptake through the biological barriers and increase the stability of the compounds - with lipoamino acids.

  已对天然产物quassin进行了修饰，以生产具有潜在抗疟疾作用的化合物。修饰包括脱甲基，降低酮的功能，用简单的有机酸进行酯化，以及-通过脂氨基酸增强通过生物屏障的摄取并提高化合物的稳定性。
• New Quassinoid Glucosides, Picrasinoside-A, -B, -C, -D, -E, -F, and -G and New Hemiacetals, Picrasinol-A and -B, from the Stem Bark of<i>Picrasma ailanthoides</i>PLANCHON
  作者：Masayoshi Okano、Tomoyuki Fujita、Narihiko Fukamiya、Takaaki Aratani

  DOI：10.1246/bcsj.58.1793

  日期：1985.6

  New quassinoid glucosides, picrasinoside-A, -B, -C, -D, -E, -F, and -G and new quassinoid hemiacetals, picrasinol-A and -B, were isolated from the stem bark of Picrasma ailanthoides PLANCHON, and their structures were established by spectral analyses and chemical transformations.

  通过光谱分析和化学转化，从 PLANCHON Picrasma ailanthoides 的茎皮中分离出新的槲皮苷葡萄糖苷-picrasinoside-A、-B、-C、-D、-E、-F 和-G 以及新的槲皮半乙酸酯-picrasinol-A 和-B，并确定了它们的结构。
• Conversion of ailanthone into shinjudilactone, a backbone-rearranged picrasane.
  作者：Masami Ishibashi、Takahiko Tsuyuki、Tatsushi Murae、Takeyoshi Takahashi

  DOI：10.1248/cpb.30.1917

  日期：——

  On heating with sodium hydrogencarbonate in aqueous methanol, ailanthone (2) afforded 13 (12→11α) abeo-picrasanes [or 9 (11→12α) abeo-picrasanes], shinjudilactone (1) and its 13-epimer (3), in a ratio of 1 : 1 in good yields. The reaction is likely to proceed through isomerization of 2 into an α-diketone (6), followed by benzilic acid rearrangement. Under the same conditions, norquassin (4) gave the rearrangement product, norquassinic acid (5).

  在甲醇水溶液中加热碳酸氢钠时，艾兰酮（2）以13（12→11α）比生成12（11→12α）比量的阿贝奥皮克拉烷、shinjudilactone（1）及其13-表异构体（3），收率较高。该反应可能通过2的异构化生成α-二酮（6），然后进行苯甲酸重排。在相同条件下，去甲奎宁（4）产生重排产物去甲奎宁酸（5）。
• PICRASINOSIDE-A, A NOVEL QUASSINOID GLUCOSIDE FROM<i>PICRASMA AILANTHOIDES</i>PLANCHON
  作者：Masayoshi Okano、Narihiko Fukamiya、Katsuhiko Kondo、Tomoyuki Fujita、Takaaki Aratani

  DOI：10.1246/cl.1982.1425

  日期：1982.9.5

  A novel quassinoid glucoside picrasinoside-A was isolated from Pierasma ailanthoides PLANCHON and the structure was established from spectral data, chemical transformations into picrasin B and quassin, and enzyme hydrolysis. The aglycon picrasin B showed a significant clastogenic activity in cell cultures of Don lung cells of Chinese hamster.

  从Pierasma ailanthoides PLANCHON中分离出一种新的奎宁甙苷类物质——苦参苷-A，并通过光谱数据、化学转化成苦参素B和奎宁以及酶水解确定了其结构。在仓鼠唐氏肺细胞培养物中，苦参素B的糖苷显示出显著的染色体断裂活性。
• Hanson et al., Journal of the Chemical Society, 1954, p. 4238,4249
  作者：Hanson et al.

  DOI：——

  日期：——