Dolabellin | 165467-49-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Dolabellin
• 英文别名: [(2R,3S)-7,7-dichloro-1-[(1S)-1-(4-methoxycarbonyl-1,3-thiazol-2-yl)-2-methylpropoxy]-2-methyl-1-oxooctan-3-yl] 2-[(1R)-1,2-dihydroxyethyl]-1,3-thiazole-4-carboxylate
• CAS: 165467-49-2
• 化学式: C₂₄H₃₂Cl₂N₂O₈S₂
• 分子量: 611.565
• InChiKey: JHKFWJUVTLNOJZ-ZSGPHXLJSA-N

物化性质

• 沸点：
  718.7±60.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  38
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  202
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Dolabellin 在 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 氢氟酸 、 sodium methylate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 46.5h， 生成 methyl 2-[(1S)-1-[(2R,3S)-3-hydroxy-2-methyloctanoyl]oxy-2-methylpropyl]-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  Dolabellin, a Cytotoxic Bisthiazole Metabolite from the Sea Hare Dolabella auricularia: Structural Determination and Synthesis

  摘要：

  Dolabellin (1), a novel cytotoxic metabolite which consists of two thiazole hydroxy acids and a new dichlorinated beta-hydroxy acid, was isolated from the Japanese sea hare Dolabella auricularia. The gross structure of 1 was elucidated on the basis of spectral data in conjunction with chemical degradations, which provided three methyl esters: methyl 2-(1-hydroxy-2 -methylpropyl)thiazole-4-carboxylate (2), methyl 2-(1,2-dihydroxyethyl)thiazole-4-carboxylate (3), and methyl 7,7-dichloro-3-hydroxy-2-methyloctanoate (4). The absolute stereochemistry of 1 was determined by stereoselective syntheses of two degradation products 2 and 3 and two diastereomeric octanoates 7a,b (the dechloro derivatives of degradation product 4), and the enantioselective total synthesis of dolabellin itself. Dechlorodolabellin (23) was also synthesized.

  DOI：

  10.1021/jo00120a021
• 作为产物：
  描述：

  Ethyl (S)-2-(1-Acetoxy-2-methylpropyl)thiazole-4-carboxylate 在 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 氢氟酸 、 sodium methylate 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 54.5h， 生成 Dolabellin
  参考文献：
  名称：

  Dolabellin, a Cytotoxic Bisthiazole Metabolite from the Sea Hare Dolabella auricularia: Structural Determination and Synthesis

  摘要：

  Dolabellin (1), a novel cytotoxic metabolite which consists of two thiazole hydroxy acids and a new dichlorinated beta-hydroxy acid, was isolated from the Japanese sea hare Dolabella auricularia. The gross structure of 1 was elucidated on the basis of spectral data in conjunction with chemical degradations, which provided three methyl esters: methyl 2-(1-hydroxy-2 -methylpropyl)thiazole-4-carboxylate (2), methyl 2-(1,2-dihydroxyethyl)thiazole-4-carboxylate (3), and methyl 7,7-dichloro-3-hydroxy-2-methyloctanoate (4). The absolute stereochemistry of 1 was determined by stereoselective syntheses of two degradation products 2 and 3 and two diastereomeric octanoates 7a,b (the dechloro derivatives of degradation product 4), and the enantioselective total synthesis of dolabellin itself. Dechlorodolabellin (23) was also synthesized.

  DOI：

  10.1021/jo00120a021

文献信息

• Dolabellin, a Cytotoxic Bisthiazole Metabolite from the Sea Hare Dolabella auricularia: Structural Determination and Synthesis
  作者：Hiroki Sone、Takashi Kondo、Minoru Kiryu、Hiroyuki Ishiwata、Makoto Ojika、Kiyoyuki Yamada

  DOI：10.1021/jo00120a021

  日期：1995.7

  Dolabellin (1), a novel cytotoxic metabolite which consists of two thiazole hydroxy acids and a new dichlorinated beta-hydroxy acid, was isolated from the Japanese sea hare Dolabella auricularia. The gross structure of 1 was elucidated on the basis of spectral data in conjunction with chemical degradations, which provided three methyl esters: methyl 2-(1-hydroxy-2 -methylpropyl)thiazole-4-carboxylate (2), methyl 2-(1,2-dihydroxyethyl)thiazole-4-carboxylate (3), and methyl 7,7-dichloro-3-hydroxy-2-methyloctanoate (4). The absolute stereochemistry of 1 was determined by stereoselective syntheses of two degradation products 2 and 3 and two diastereomeric octanoates 7a,b (the dechloro derivatives of degradation product 4), and the enantioselective total synthesis of dolabellin itself. Dechlorodolabellin (23) was also synthesized.