(5-硝基-1-苯并呋喃-2-基)甲醇 | 90322-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: (5-硝基-1-苯并呋喃-2-基)甲醇
• 英文名称: (5-nitrobenzofuran-2-yl)methanol
• 英文别名: (5-nitro-1-benzofuran-2-yl)methanol
• CAS: 90322-48-8
• 化学式: C₉H₇NO₄
• mdl: MFCD10758066
• 分子量: 193.159
• InChiKey: SAIWPSXAGFHMTA-UHFFFAOYSA-N

物化性质

• 熔点：
  117-119°
• 沸点：
  373.0±27.0 °C(Predicted)
• 密度：
  1.463±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  (5-硝基-1-苯并呋喃-2-基)甲醇 在 bis(η3-allyl-μ-chloropalladium(II)) 、 potassium carbonate 、 三乙胺 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  钯催化苯并呋喃-2-基甲基乙酸酯与亲核试剂的 Tsuji-Trost 型反应。

  摘要：

  研究了钯催化的苯并呋喃-2-基甲基乙酸酯与 N、S、O 和 C 软亲核试剂的类苄基亲核取代反应。反应的成功很大程度上取决于催化体系的选择：对于氮基亲核试剂，反应与 Pd2(dba)3/dppf 反应良好，而对于硫、氧和碳亲核试剂 [Pd(η3-C3H5)Cl] 2/XPhos 效率更高。区域化学结果表明，亲核取代仅发生在 η3-(苯并呋喃基)甲基配合物的苄位上。高至优异的产率和实验程序的简单性使该方案成为制备 2-取代苯并[b]呋喃的通用合成工具。

  DOI：

  10.1039/d0ra09601f
• 作为产物：
  描述：

  5-硝基-1-苯并呋喃-2-甲醛 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以63.5%的产率得到(5-硝基-1-苯并呋喃-2-基)甲醇
  参考文献：
  名称：

  A Novel Model System for Understanding Anticancer Activity of Hypoxia-Activated Prodrugs

  摘要：

  Reports on the comprehensive factors for design considerations of hypoxia-activated prodrugs (HAPs) are rare. We introduced a new model system composed of a series of highly water-soluble HAPs, providing a platform to comprehensively understand the interaction between HAPs and hypoxic biosystems. Specifically, four kinds of new HAPs were designed and synthesized, containing the same biologically active moiety but masked by different bioreductive groups. Our results demonstrated that the activity of the prodrugs was strongly dependent on not only the molecular structure but also the hypoxic tumor microenvironment. We found the presence of a direct linear relationship between cytotoxicity of the HAPs and the reduction potential of whole molecule/oxygen concentration/reductase expression. Moreover, limited blood vasculature in hypoxic regions was also a critical barrier for effective activation of the HAPs. This study offers a comprehensive insight into understanding the design factors required for HAPs.

  DOI：

  10.1021/acs.molpharmaceut.0c00232

文献信息

• Benzoxazepinones and their use as squalene synthase inhibitors
  申请人：——

  公开号：US20030078251A1

  公开（公告）日：2003-04-24

  There is disclosed a compound represented by the formula [I]: 1 wherein R 1 is optionally substituted 1-carboxyethyl group, optionally substituted alkyl-sulfonyl group, optionally substituted (carboxy-cycloalkyl)-alkyl group, —X 1 —X 2 —Ar—X 3 —X 4 —COOH (wherein X 1 and X 4 are a bond or alkylene group, X 2 and X 3 are a bond, —O—, —S—, Ar is divalent aromatic group etc.), R 2 is alkyl group optionally substituted with alkanoyloxy group and/or hydroxy group, R 3 is alkyl group, and W is halogen atom, etc., or a salt thereof. The compound has the cholesterol lowering activity and the triglyceride lowering activity and is useful for preventing and/or treating hyperlipidemia.

  披露了一种由公式[I]表示的化合物： 1 其中R 1 是可选地取代的1-羧乙基，可选地取代的烷基亚磺酰基，可选地取代的(羧基环烷基)-烷基，—X 1 —X 2 —Ar—X 3 —X 4 —COOH(其中X 1 和X 4 是键或亚烷基，X 2 和X 3 是键，—O—，—S—，Ar是二价芳香族等)，R 2 是可选地由酰氧基和/或羟基取代的烷基，R 3 是烷基，W是卤素原子等，或其盐。该化合物具有降低胆固醇活性和降低甘油三酯活性，用于预防或治疗高脂血症。
• Derivatives of Pyrido[2,3-d]pyrimidine, the Preparation Thereof, and the Therapeutic Application of the Same
  申请人：BOURRIE Bernard

  公开号：US20080176874A1

  公开（公告）日：2008-07-24

  The invention relates to derivatives of pyrido[2,3-d]pyrimidine, to the preparation thereof, and to the therapeutic application of the same.

  本发明涉及吡啶并[2,3-d]嘧啶衍生物，其制备方法以及它们的药用应用。
• [EN] ANTI-HIV COMPOUNDS<br/>[FR] COMPOSÉS ANTI-VIH
  申请人：PANACOS PHARMACEUTICALS INC

  公开号：WO2009085256A1

  公开（公告）日：2009-07-09

  Thiazole derivatives represented by Formula (I) are disclosed, where R1, R2, R3, A, X, Y, Z, R6 and R7 are disclosed herein. These thiazole derivatives and pharmaceutical compositions comprising these derivatives are useful in the treatment of HIV mediated diseases and conditions.

  公式（I）代表的噻唑衍生物已被披露，其中在此披露了R1、R2、R3、A、X、Y、Z、R6和R7。这些噻唑衍生物和包含这些衍生物的药物组合物在治疗HIV介导的疾病和症状方面是有用的。
• Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids
  作者：Antonella Goggiamani、Antonia Iazzetti、Antonio Arcadi、Andrea Calcaterra、Marco Chiarini、Giancarlo Fabrizi、Andrea Fochetti、Federico Marrone、Vincenzo Marsicano、Andrea Serraiocco

  DOI：10.1055/s-0041-1737275

  日期：2022.2

  The palladium-catalyzed synthesis of indole/benzofuran-containing diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient

  已经研究了从吲哚甲基或苯并呋喃甲基乙酸酯与硼酸开始钯催化合成含有吲哚/苯并呋喃的二芳基甲烷。反应的成功受预催化剂选择的影响：对于吲哚基乙酸甲酯，该反应与 [Pd(η 3 -C 3 H 5 )Cl] 2 /XPhos反应良好，而对于苯并呋喃基乙酸甲酯 Pd 2 (dba) 3 /XPhos 则反应良好更高效。良好的高产率和实验程序的简单性使该方案成为制备 2-和 3-取代吲哚和 2-苯并[ b]的通用合成工具]呋喃。该方法可以有利地扩展到扎鲁司特的关键前体的制备。
• Pd/C mediated synthesis of 2-substituted benzo[b]furans/nitrobenzo[b]furans in water
  作者：Manojit Pal、Venkataraman Subramanian、Koteswar Rao Yeleswarapu

  DOI：10.1016/j.tetlet.2003.09.080

  日期：2003.11

  ns in water has been accomplished via Pd/C catalyzed reaction of o-iodophenols with terminal alkynes in the presence of PPh3, CuI and prolinol. This method can tolerate a variety of functional groups present in the alkynes as well as base labile nitro group in the o-iodophenols. The protocol does not require the use of a phase transfer catalyst or water-soluble phosphine ligands and is free from the

  2-烷基/芳基取代的苯并[一种高效合成b ]呋喃/硝基苯并[ b / C]水呋喃已经经由钯而完成催化反应ö与PPH的存在末端炔烃-iodophenols 3，碘化亚铜和脯氨醇。该方法可以耐受炔烃中存在的各种官能团以及邻碘苯酚中的碱不稳定的硝基。该方案不需要使用相转移催化剂或水溶性膦配体，并且无需使用任何有机助溶剂。