grossularine-2 | 102488-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: grossularine-2
• 英文别名: [4-(dimethylamino)-3,5,8,10-tetrazatetracyclo[7.7.0.02,6.011,16]hexadeca-1,3,6,8,11,13,15-heptaen-7-yl]-(4-hydroxyphenyl)methanone
• CAS: 102488-58-4
• 化学式: C₂₁H₁₇N₅O₂
• 分子量: 371.398
• InChiKey: OGSOWFWOXWWJSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  97.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 grossularine-2 在 吡啶 作用下， 反应 24.0h， 生成 Acetic acid 4-(6-acetyl-2-dimethylamino-3,6-dihydro-1,3,5,6-tetraaza-cyclopenta[c]fluorene-4-carbonyl)-phenyl ester
  参考文献：
  名称：

  Grossularine-1 and grossularine-2, cytotoxic α-carbolines from the tunicate: Dendrodoa grossularia

  摘要：

  DOI：

  10.1016/s0040-4020(01)81023-1
• 作为产物：
  描述：

  11-(Dimethylamino)-2-(methoxycarbonyl)-9H-imidazo<4',5':3,4>pyrido<2,3-b>indole 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.25h， 生成 grossularine-2
  参考文献：
  名称：

  Total synthesis of grossularines-1 and -2

  摘要：

  The first total syntheses of grossularines-1 (1a) and -2 (1b) have been completed. The cross-coupling reaction between ethyl 3-iodoindole-2-carboxylate (6) and the directed metalation-derived imidazole 9b gave the ethyl 3-(5-imidazolyl)indole-2-carboxylate 11b. Hydrolysis of the ester group of 11b, followed by Curtius rearrangement, yielded the 2-isocyanatoindole 13b. The thermal electrocyclic reaction of 13b was carried out to provide the desired tetracyclic pyrido[2,3-b]indole ring system 14b, which was converted into the triflate 15b. The three-component cross-coupling reaction of the triflate 15b, carbon monoxide, and p-(OMOM)phenylboronic acid (17) followed by hydrolysis gave grossularine-2 (1b) in low yield. In addition, the palladium-catalyzed carbonylation of the triflate 15b afforded the N-deprotected methyl ester 19a or the methyl ester 19b depending on the amounts of triethylamine used. Compound 19a was treated with either p-(OMOM)phenyllithium or 3-(N-TIPS)indolyllithium to obtain grossularine-2 (1b) and grossularine-1 (1a) (37%), respectively. By contrast, when 19b was treated with the same aryllithium reagents, grossularine-2 (1b) (51%) and grossularine-1 (1a) (63%) were produced, respectively.

  DOI：

  10.1021/jo00123a028

文献信息

• Total synthesis of grossularines-1 and -2
  作者：Tominari Choshi、Shiho Yamada、Eiichi Sugino、Takeshi Kuwada、Satoshi Hibino

  DOI：10.1021/jo00123a028

  日期：1995.9

  The first total syntheses of grossularines-1 (1a) and -2 (1b) have been completed. The cross-coupling reaction between ethyl 3-iodoindole-2-carboxylate (6) and the directed metalation-derived imidazole 9b gave the ethyl 3-(5-imidazolyl)indole-2-carboxylate 11b. Hydrolysis of the ester group of 11b, followed by Curtius rearrangement, yielded the 2-isocyanatoindole 13b. The thermal electrocyclic reaction of 13b was carried out to provide the desired tetracyclic pyrido[2,3-b]indole ring system 14b, which was converted into the triflate 15b. The three-component cross-coupling reaction of the triflate 15b, carbon monoxide, and p-(OMOM)phenylboronic acid (17) followed by hydrolysis gave grossularine-2 (1b) in low yield. In addition, the palladium-catalyzed carbonylation of the triflate 15b afforded the N-deprotected methyl ester 19a or the methyl ester 19b depending on the amounts of triethylamine used. Compound 19a was treated with either p-(OMOM)phenyllithium or 3-(N-TIPS)indolyllithium to obtain grossularine-2 (1b) and grossularine-1 (1a) (37%), respectively. By contrast, when 19b was treated with the same aryllithium reagents, grossularine-2 (1b) (51%) and grossularine-1 (1a) (63%) were produced, respectively.
• Grossularine-1 and grossularine-2, cytotoxic α-carbolines from the tunicate: Dendrodoa grossularia
  作者：Carole Moquin-Pattey、Michèle Guyot

  DOI：10.1016/s0040-4020(01)81023-1

  日期：1989.1

表征谱图