4-pentyl-chromen-2-one

• 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: 4-pentyl-chromen-2-one
• 英文别名: 4-pentyl-2H-chromen-2-one；4-Pentylchromen-2-one
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: PNMBLAGZSGYCFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-pentylnaphthalene-1,2-dione 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 氧气 、 1,4-双(二苯基膦)丁烷 作用下， 以 甲苯 为溶剂， 反应 60.0h， 以54%的产率得到4-pentyl-1H-isochromen-1-one
  参考文献：
  名称：

  铑（I）催化的环状α-二酮的脱羰好氧氧化：区域选择性单碳挤出策略。

  摘要：

  首次开发了铑催化的环状α-二酮的去羰基好氧氧化反应，在该反应中已经实现了α-吡喃酮和异香豆素的区域选择性形成。当前的脱羰需氧氧化途径是通过C–C键断裂，然后形成C–O键进行的，这代表了对不饱和六元环内酯的仿生氧化方法。铑催化剂具有独特的诱导脱羰需氧氧化的能力，从而开辟了利用“区域选择性单碳”挤出策略的新型合成工具箱。

  DOI：

  10.1021/acs.orglett.7b03837

文献信息

• Microwave-accelerated, palladium-catalyzed carbonylative cyclization reactions of 2-iodophenol with alkynes — Rapid and efficient synthesis of chromen-2-one derivatives
  作者：Hong Cao、Wen-Jing Xiao

  DOI：10.1139/v05-094

  日期：2005.6.1

  Rapid palladium-catalyzed carbonylative cyclization reactions of 2-iodophenol with various alkynes have been carried out by the use of commercially available molybdenum hexacarbonyl as a convenient and solid carbon monoxide source. The reactions were conducted at 160 °C for 30 min with microwave heating in the presence of DIEA and DMAP in 1,4-dioxane, and afford the corresponding chromen-2-one derivatives

  2-碘苯酚与各种炔烃的快速钯催化羰基化环化反应已通过使用市售六羰基钼作为方便和固体一氧化碳源进行。在DIEA和DMAP的存在下，在1,4-二恶烷中，在160°C和微波加热下进行反应30分钟，并以良好的收率得到相应的chromen-2-one衍生物。 关键词：微波，钯，羰基化, 2-iodophenol, chromen-2-one。
• [EN] ANTI-VASCULATURE AND ANTI-TUBULIN COMBRETASTATIN ANALOGS FOR TREATMENT OF CANCER<br/>[FR] ANALOGUES DE COMBRÉTASTATINE ANTI-VAISSEAUX SANGUINS ET ANTI-TUBULINE POUR LE TRAITEMENT DU CANCER
  申请人：XAVIER UNIVERSITY OF LOUISIANA

  公开号：WO2015153252A1

  公开（公告）日：2015-10-08

  Combretastatins analog compounds and their pharmaceutically acceptable salts are presented, as well as pharmaceutical compositions comprising the combretastatin analog compounds and uses of the combretastatin analog compounds, either alone or in combination with at least one additional therapeutic agent, in the treatment of cancer, and in particular cancer presenting as metastatic tumors.

  提供了Combretastatins类似化合物及其药用可接受的盐，以及包含Combretastatins类似化合物的药物组合物，以及Combretastatins类似化合物的用途，无论是单独使用还是与至少一种额外治疗剂联合使用，用于治疗癌症，特别是表现为转移性肿瘤的癌症。
• Chromene-containing compounds with anti-tubulin and vascular targeting activity
  申请人：Pinney G. Kevin

  公开号：US20050245489A1

  公开（公告）日：2005-11-03

  Trimethoxyphenyl substituted indole ligands have been discovered which demonstrate impressive cytotoxicity as well as a remarkable ability to inhibit tubulin polymerization. Such compounds as well as related derivatives are excellent clinical candidates for the treatment of cancer in humans. In addition, certain of these ligands, as pro-drugs, may well prove to be tumor selective vascular targeting chemotherapeutic agents or to have vascular targeting activity resulting in the selective prevention and/or destruction of nonmalignant proliferating vasculature.

  已发现取代了三甲氧基苯基的吲哚配体，表现出令人印象深刻的细胞毒性以及抑制微管聚合的显著能力。这些化合物以及相关衍生物是治疗人类癌症的优秀临床候选药物。此外，这些配体中的某些作为前药，可能证明是肿瘤选择性血管靶向化疗药物，或具有血管靶向活性，从而选择性地预防和/或破坏非恶性增殖血管。
• Novel coumarin-amide derivatives and its preparation, said drug composition and its use
  申请人：Xu Shiping

  公开号：US20060148834A1

  公开（公告）日：2006-07-06

  The present invention relates to novel coumarin derivatives, their carboxamides, pharmaceutical compositions containing them and their uses as drugs for kidney protection, treating drugs of hypertension, cardio-cerebrovascular diseases, non-insulin dependent diabetes, tumor, pre-cancerous lesion, and edemas.

  本发明涉及新型香豆素衍生物，它们的羧酰胺，包含它们的制药组合物以及它们作为肾脏保护药物、治疗高血压、心脑血管疾病、非胰岛素依赖性糖尿病、肿瘤、癌前病变和水肿的用途。
• Method for the preparation of (+/-)-calanolide A
  申请人：MEDICHEM RESEARCH, INC.

  公开号：EP1054007A2

  公开（公告）日：2000-11-22

  A method of preparing (±)-calanolide A, 1, a potent HIV reverse transcriptase inhibitor, from chromene 4 is provided. Useful intermediates for preparing (±)-calanolide A and its derivatives are also provided. According to the disclosed method, chromene 4 intermediate was reacted with acetaldehyde diethyl acetal or paraldehyde in the presence of an acid catalyst with heating, or a two-step reaction including an aldol reaction with acetaldehyde and cyclization either under acidic conditions or neutral Mitsunobu conditions, to produce chromanone 7. Reduction of chromanone 7 with sodium borohydride, in the presence of cerium trichloride, produced (±)-calanolide A. A method for resolving (±)-calanolide A into its optically active forms by a chiral HPLC system or by enzymatic acylation and hydrolysis is also disclosed. Finally, a method for treating or preventing viral infections using (±)-calanolide or (-)-calanolide is provided.

  本研究提供了一种由色烯 4 制备 (±)-calanolide A, 1 的方法，(±)-calanolide A, 1 是一种有效的 HIV 逆转录酶抑制剂。还提供了制备 (±)-calanolide A 及其衍生物的有用中间体。根据所公开的方法，在酸性催化剂存在下，加热铬烯 4 中间体与乙醛二乙缩醛或副醛反应，或在酸性条件下或中性三忍条件下进行两步反应，包括与乙醛的醛醇反应和环化反应，生成色满酮 7。在三氯化铈存在下，用硼氢化钠还原色满酮 7，生成(±)-丙醇内酯 A。此外，还公开了一种通过手性 HPLC 系统或酶酰化和水解将 (±)-calanolide A 分解为其光学活性形式的方法。最后，还提供了一种使用 (±)-calanolide 或 (-)-calanolide 治疗或预防病毒感染的方法。