homofascaplysin B | 132938-12-6

• 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: homofascaplysin B
• 英文别名: Oxo-(12H-pyrido[1,2-a；methyl 2-(3,13-diazapentacyclo[11.7.0.02,10.04,9.014,19]icosa-1(20),2(10),4,6,8,11,14,16,18-nonaen-20-yl)-2-oxoacetate
• CAS: 132938-12-6
• 化学式: C₂₁H₁₄N₂O₃
• 分子量: 342.354
• InChiKey: JSCOOTAVKPBHTB-UHFFFAOYSA-N

物化性质

• 沸点：
  417.7±27.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-[2-(indol-1-yl)ethyl]-1H-indole 在 palladium on activated charcoal 二乙二醇二乙醚 、 三氟乙酸 作用下， 反应 10.75h， 生成 homofascaplysin B
  参考文献：
  名称：

  Total syntheses of the marine sponge pigments fascaplysin and homofascaplysin B and C

  摘要：

  The Fascaplysinopsis spp. marine sponge pigments fascaplysin (1), homofascaplysin B (4), and homofascaplysin C (5) have been synthesized by peracid oxidation, reaction with oxalyl chloride/methanol, or Vilsmeier formylation, respectively, of the keystone intermediate 12H-pyrido[1,2-a:3,4-b']diindole (7). The versatile 7 was prepared from indole (17) in six steps (78% yield), a sequence in which the key reaction is the trifluoroacetic acid-induced ring closure of diindole 15, followed by Pd/C-catalyzed dehydrogenation of the crude mixture of cyclized products 25, 26, to give 7 in 93% yield from 15.

  DOI：

  10.1021/jo00039a024

文献信息

• Synthesis of homofascaplysin B, C and analogues by the photocyclization of 3-acyl-2-chloro-1-[2-(indol-3-yl)ethyl]indoles
  作者：Yisi Dai、Wenxue Zhang、Kongchen Wang、Weixia Wang、Wei Zhang

  DOI：10.1016/j.tet.2012.12.041

  日期：2013.2

  of 2-chloro-3-acyl-1-[2-(indol-3-yl)ethyl]indoles in acetone and DDQ-mediated dehydrogenation of 13-acyl-6,7-dihydro-pyrido[1,2-a;3,4-b′]diindoles in benzene at room temperature. Comparatively, the two-step route for the synthesis of homofascaplysin B, C and analogues is more efficient than the one-pot route.

  使用光环化作为关键步骤，已经建立了两种合成高法丝素B，C和类似物的途径。第一条路线是基于在Cu（OAc）2中的2-氯-3-酰基-1- [2-（吲哚-3-基）乙基]吲哚和空气饱和丙酮的顺序光环化和光化学脱氢反应。第二步是基于两步反应的，即2-氯-3-酰基-1-[[2-（吲哚-3-基）乙基]吲哚在丙酮中的光环化和DDQ介导的13-酰基脱氢室温下苯中的-6,7-二氢吡啶并[1,2- a ; 3,4- b ']二吲哚。相比之下，用于合成高法丝溶素B，C和类似物的两步法比一锅法更有效。
• One-step transformation of the marine alkaloid fascaplysin into homofascaplysins B and B-1. The first syntheses of 3-bromohomofascaplysin B and 3–bromohomofascaplysin B-1
  作者：Maxim E. Zhidkov、Maria A. Sidorova、Irina A. Lyakhova

  DOI：10.1016/j.tetlet.2018.02.070

  日期：2018.4

  A method for one-step conversion of the marine alkaloid fascaplysin into homofascaplysins B and B-1 was elaborated. It was also used for the first syntheses of the marine alkaloids 3-bromohomofascaplysin B and 3-bromohomofascaplysin B-1. The best results were demonstrated under the action of microwave irradiation in presents of dihydroquinone as a reducing agent. (C) 2018 Elsevier Ltd. All rights reserved.
• Total syntheses of the marine sponge pigments fascaplysin and homofascaplysin B and C
  作者：Gordon W. Gribble、Benjamin Pelcman

  DOI：10.1021/jo00039a024

  日期：1992.6

  The Fascaplysinopsis spp. marine sponge pigments fascaplysin (1), homofascaplysin B (4), and homofascaplysin C (5) have been synthesized by peracid oxidation, reaction with oxalyl chloride/methanol, or Vilsmeier formylation, respectively, of the keystone intermediate 12H-pyrido[1,2-a:3,4-b']diindole (7). The versatile 7 was prepared from indole (17) in six steps (78% yield), a sequence in which the key reaction is the trifluoroacetic acid-induced ring closure of diindole 15, followed by Pd/C-catalyzed dehydrogenation of the crude mixture of cyclized products 25, 26, to give 7 in 93% yield from 15.