lamellarin U diisopropyl ether | 215715-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: lamellarin U diisopropyl ether
• 英文别名: 8,16,17-Trimethoxy-12-(4-methoxy-3-propan-2-yloxyphenyl)-7-propan-2-yloxy-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18-octaen-3-one
• CAS: 215715-41-6
• 化学式: C₃₅H₃₇NO₈
• 分子量: 599.681
• InChiKey: IAELHOGMPZDEDM-UHFFFAOYSA-N

物化性质

• 熔点：
  210.5-211.5 °C
• 沸点：
  768.4±60.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  86.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  lamellarin U diisopropyl ether 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 48.0h， 以93%的产率得到3-isopropoxy-14-(3-isopropoxy-4-methoxyphenyl)-2,11,12-trimethoxy-6H-[1]benzopyrano-[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one
  参考文献：
  名称：

  Total synthesis and evaluation of lamellarin α 20-Sulfate analogues

  摘要：

  In order to explore the influence of sulfate groups on the bioactivity profiles of marine alkaloids of the lamellarin class, three such alkaloids, lamellarin alpha, lamellarin alpha 13,20-disulfate and lamellarin H, were synthesized and their activities against HIV-1 integrase and cancer cell lines were compared with those of lamellarin alpha 20-sulfate, which is a selective inhibitor of HIV-1 integrase. Lamellarin alpha does not inhibit HIV-1 integrase but shows moderate cytotoxicity with good cell line selectivity. Lamellarin alpha 13,20-disulfate is a moderate inhibitor of both HIV-1 integrase and cancer cell lines. Lamellarin H is a more potent inhibitor of HIV-1 integrase but lacked the specificity required to be medicinally useful. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00237-7
• 作为产物：
  描述：

  2-iodo-5-isopropoxy-4-methoxybenzaldehyde 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 copper(l) iodide 、 氨 、 potassium hydrogencarbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 64.0h， 生成 lamellarin U diisopropyl ether
  参考文献：
  名称：

  Total synthesis and evaluation of lamellarin α 20-Sulfate analogues

  摘要：

  In order to explore the influence of sulfate groups on the bioactivity profiles of marine alkaloids of the lamellarin class, three such alkaloids, lamellarin alpha, lamellarin alpha 13,20-disulfate and lamellarin H, were synthesized and their activities against HIV-1 integrase and cancer cell lines were compared with those of lamellarin alpha 20-sulfate, which is a selective inhibitor of HIV-1 integrase. Lamellarin alpha does not inhibit HIV-1 integrase but shows moderate cytotoxicity with good cell line selectivity. Lamellarin alpha 13,20-disulfate is a moderate inhibitor of both HIV-1 integrase and cancer cell lines. Lamellarin H is a more potent inhibitor of HIV-1 integrase but lacked the specificity required to be medicinally useful. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00237-7

文献信息

• Regioselective Synthesis of 2,4-Differentially Arylated Pyrroles and Its Application to The Synthesis of Lamellarins
  作者：Masatomo Iwao、Tsutomu Fukuda、Mizuho Anzai

  DOI：10.3987/com-15-s(t)49

  日期：——

  been developed. In the last decade, several strategies for the synthesis of 2,4-differentially arylated pyrroles have been reported. They involve the interesting key reactions such as ring formation from 1,3-diaryl-4-nitrobutan-1-ones, carbanion induced pyrrole synthesis from azirines and ketones, ozonolysis of homoallylic ketones followed by Paal–Knorr condensation, gold-catalyzed reaction with N-tosyl

  通过逐步钯催化的 Suzuki-Miyaura 偶联 N-苯磺酰基-4-溴-2-碘吡咯与不同的芳基硼酸，开发了一种合成 2,4-差异芳基化吡咯的有效方法。该方法已应用于海洋天然产物板层素的新合成。引言 吡咯衍生物广泛存在于具有广泛生物活性的天然产物中。它们也嵌入在一些药剂中。此外，它们还被用作制备具有独特电子和光物理特性的功能材料的宝贵组成部分。因此，已经开发了多种用于从头构建环和对吡咯核进行区域选择性功能化的合成方法。在过去的十年里，已经报道了几种合成 2,4-差异芳基化吡咯的策略。它们涉及有趣的关键反应，例如 1,3-diaryl-4-nitrobutan-1-ones 的成环反应、碳负离子诱导的氮杂环丙烷和酮合成吡咯、高烯丙基酮的臭氧分解以及 Paal-Knorr 缩合、金催化反应N-甲苯磺酰基炔基氮丙啶，铑催化的 N-甲苯磺酰基-1,2,3-三唑与末端炔烃或烯基烷基醚的环化反应，铜
• Scalable Total Syntheses of Some Natural and Unnatural Lamellarins: Application of a One-Pot Domino Process for Regioselective Access to the Central 1,2,4-Trisubstituted Pyrrole Core
  作者：Virendra Kumar、Annapurna Awasthi、Abdus Salam、Tabrez Khan

  DOI：10.1021/acs.joc.9b01521

  日期：2019.9.20

  Short and scalable total syntheses of lamellarin G trimethyl ether, lamellarin D trimethyl ether, lamellarin H, lamellarin η, dihydrolamellarin η, and lamellarin U have been realized in four to six linear steps with an overall yield of ≤22%. Highlights of the synthesis include single-step access to the central 1,2,4-trisubstituted pyrrole core in a highly regioselective manner via a one-pot [3+2]

  lamellarin G三甲基醚，lamellarin D三甲基醚，lamellarin H，lamellarinη，二氢lamellarinη和lamellarin U的短而可扩展的总合成已通过四至六个线性步骤实现，总收率≤22％。合成的重点包括通过基于一锅[3 + 2]环加成/消除/芳香化序列的多米诺法，以高度区域选择性的方式一步一步进入中心1,2,4-三取代的吡咯核心。随后，在单锅操作中，钯介导的双CH氧化双偶联提供了层状蛋白中存在的五环香豆素融合的吡咯并二氢异喹啉核心的通道。