3-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one | 31490-70-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one
• 英文别名: isoprenyl coumarin；4-Hydroxy-3-(3-methyl-but-2-enyl)-chromen-2-one；4-hydroxy-3-(3-methylbut-2-enyl)chromen-2-one
• CAS: 31490-70-7
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: YRWFXMOTWDSLNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one 在 硫酸 作用下， 反应 1.0h， 以50%的产率得到2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]chromen-5-one
  参考文献：
  名称：

  Synthetic methods for the preparation of ARQ 501 (β-Lapachone) human blood metabolites

  摘要：

  ARQ 501 (3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione), a synthetic version of beta-Lapachone, is a promising anti-cancer agent currently in multiple Phase II clinical trials. Promising anti-cancer activity was observed in Phase I and Phase II trials. Metabolism by red blood cells of drugs is an understudied area of research and the metabolites arising from oxidative ring opening (M2 and M3), decarbonylation/ ring contraction (M5), and decarbonylation/ oxidation (M4 and M6) of ARQ 501 offer a unique opportunity to provide insight into these metabolic processes. Since these metabolites were not detected in in vitro incubations of ARQ 501 with liver microsomes and were structurally diverse, confirmation by chemical synthesis was considered essential. In this report, we disclose the synthetic routes employed and the characterization of the reference standards for these blood metabolites as well as additional postulated structures, which were not confirmed as metabolites. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.073
• 作为产物：
  描述：

  异戊烯醇 在 sodium hydroxide 、 三溴化磷 、 lithium diisopropyl amide 作用下， 以 乙醇 、 正戊烷 为溶剂， 反应 3.92h， 生成 3-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  A Regioselective Synthesis of 3-Isoprenyl-4-Hydroxycoumarins

  摘要：

  the dianion of ethyl 3-(2-hydroxyphenyl)-3-oxopropanoate can be regioselectively alkylated with isoprenyl bromides to give, after hydrolytic work-up, the corresponding 3-substituted-4-hydroxycoumarins.

  DOI：

  10.1080/00397919208019073

文献信息

• In(OTf)₃-catalysed easy access to dihydropyranocoumarin and dihydropyranochromone derivatives
  作者：Naouel Boufroua、Elisabet Dunach、Fabien Fontaine-Vive、Samia Achouche-Bouzroura、Sophie Poulain-Martini

  DOI：10.1039/d0nj00080a

  日期：——

  Allylation/cyclization of β-ketolactone-type heterocyclic compounds, under In(OTf)₃-catalysis, for the construction of biologically active dihydropyranocoumarin and dihydropyranochromone derivatives.

  β-酮内酯类杂环化合物的烯丙基化/环化反应，在In(OTf)₃催化下进行，用于构建具有生物活性的二氢吡喃香豆素和二氢吡喃色酮衍生物。
• Synthetic methods for the preparation of ARQ 501 (β-Lapachone) human blood metabolites
  作者：Rui-Yang Yang、Darin Kizer、Hui Wu、Erika Volckova、Xiu-Sheng Miao、Syed M. Ali、Manish Tandon、Ronald E. Savage、Thomas C.K. Chan、Mark A. Ashwell

  DOI：10.1016/j.bmc.2008.03.073

  日期：2008.5

  ARQ 501 (3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione), a synthetic version of beta-Lapachone, is a promising anti-cancer agent currently in multiple Phase II clinical trials. Promising anti-cancer activity was observed in Phase I and Phase II trials. Metabolism by red blood cells of drugs is an understudied area of research and the metabolites arising from oxidative ring opening (M2 and M3), decarbonylation/ ring contraction (M5), and decarbonylation/ oxidation (M4 and M6) of ARQ 501 offer a unique opportunity to provide insight into these metabolic processes. Since these metabolites were not detected in in vitro incubations of ARQ 501 with liver microsomes and were structurally diverse, confirmation by chemical synthesis was considered essential. In this report, we disclose the synthetic routes employed and the characterization of the reference standards for these blood metabolites as well as additional postulated structures, which were not confirmed as metabolites. (C) 2008 Elsevier Ltd. All rights reserved.
• A Regioselective Synthesis of 3-Isoprenyl-4-Hydroxycoumarins
  作者：G. Appendino、G. Cravotto、G. M. Nano、G. Palmisano

  DOI：10.1080/00397919208019073

  日期：1992.8

  the dianion of ethyl 3-(2-hydroxyphenyl)-3-oxopropanoate can be regioselectively alkylated with isoprenyl bromides to give, after hydrolytic work-up, the corresponding 3-substituted-4-hydroxycoumarins.