methyl 4-hydroxybenzofuran-5-carboxylate | 60077-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-hydroxybenzofuran-5-carboxylate
• 英文别名: methyl 4-hydroxy-1-benzofuran-5-carboxylate
• CAS: 60077-57-8
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: HYRURJQQQURGQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  methyl 4-hydroxybenzofuran-5-carboxylate 在 哌啶 、 sodium hydride 作用下， 以 甲苯 、 苯 为溶剂， 生成 lanceolatin B
  参考文献：
  名称：

  铑类胡萝卜素与乙烯基酯的偶极环加成。pongamol和lanceolatin B的全合成

  摘要：

  一种重氮偶氮环己烷-1,3-二酮偶极环加成反应的新方法，可产生苯并呋喃衍生物，已被用于全合成来自提弗罗西亚和庞加米的天然产物。

  DOI：

  10.1016/s0040-4039(00)73399-5
• 作为产物：
  描述：

  methyl 4-oxo-4,5,6,7-tetrahydro-1-benzofuran-5-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以85%的产率得到methyl 4-hydroxybenzofuran-5-carboxylate
  参考文献：
  名称：

  通过硝酸铈 (IV) 铵介导的 1,3-二羰基化合物与乙烯基硫化物的氧化环加成高效合成具有硫化物基团的二氢呋喃。在苯并[b]萘并[2,3-d]呋喃-6,11-二酮的合成中的应用及首次全合成小米花萼C和黄甲酚甲醚

  摘要：

  Ceric(IV) 硝酸铵介导的 1,3-二羰基与乙烯基硫化物的氧化环加成反应以中等收率提供了具有硫化物基团的取代二氢呋喃。这种新的合成方法已应用于苯并[b]萘并[2,3-d]呋喃-6,11-二酮和呋喃黄酮类天然产物如小米花萼素C、凤梨甲醚的合成。

  DOI：

  10.1055/s-2003-41023

文献信息

• A Controlled Synthesis of Nature-Mimicking Benzofurans and their Corresponding Dimers
  作者：Atul Goel、Manish Dixit、Ashoke Sharon、Prakas Maulik

  DOI：10.1055/s-2006-944194

  日期：2006.6

  Benzofurans functionalized with hydroxy and acetyl functionalities are not only the core structures found in a large number of biologically important natural products, but also the vital precursors for several naturally occurring furanoflavonoids. Numerous synthetic methodologies are available in the literature for the ­synthesis of functionalized benzofurans but access to benzofurans with adjacent hydroxy and acetyl functionalities shows paucity of references. In this paper we report highly convenient synthesis of nature-mimicking benzofurans and their dimers from easily accessible precursors.

  羟基和乙酰基官能化的苯并呋喃不仅是大量生物活性天然产物中的核心结构，也是多种天然存在的呋喃黄酮类化合物的重要前体。文献中提供了许多合成官能化苯并呋喃的方法，但关于邻位羟基和乙酰基官能化苯并呋喃的文献却很少。本文中，我们报道了从易得的前体出发，高度便捷地合成仿生苯并呋喃及其二聚体的方法。
• The isolation and synthesis of a novel benzofuran compound from Tephrosia purpurea, and the synthesis of several related derivatives, which suppress histamine H1 receptor gene expression
  作者：Manik Chandra Shill、Asish Kumar Das、Tomohiro Itou、Sanmoy Karmakar、Pulok K. Mukherjee、Hiroyuki Mizuguchi、Yoshiki Kashiwada、Hiroyuki Fukui、Hisao Nemoto

  DOI：10.1016/j.bmc.2015.09.049

  日期：2015.11

  A novel naturally occurring compound with a benzofuran skeleton was isolated from a plant, Tephrosia purpurea collected in Bangladesh. The chemical synthesis of this compound confirmed its structure, and preliminary biological results showed its suppressive activity towards histamine H1 gene expression. One isomer and four derivatives were also synthesized, and their suppression activity was investigated

  从孟加拉国收集的一种植物Tephrosia purpurea中分离出了一种具有苯并呋喃骨架的新型天然化合物。该化合物的化学合成证实了其结构，初步的生物学结果表明其对组胺H 1基因表达具有抑制活性。还合成了一种异构体和四种衍生物，并研究了它们的抑制活性。尽管只能从其天然来源中分离出少量这种化合物，但新开发的方法证明了10 g规模的合成。
• First asymmetric total synthesis of Millpuline B
  作者：Hongbo Dong、Min Wu、Weihong Du、Mingwei Shong、Yujiao He、Yuchi Wang

  DOI：10.1080/00397911.2021.2001018

  日期：2022.1.2

  Abstract Millpuline B (1), isolated from Millettia pulchra, is a naturally occurring bioactive compound with a chiral center. Herein, we report the first total syntheses of both (+/-)-Millpuline B from commercal available 6,7-dihydro-4(5H)-benzofuranone (4) using Grignard reaction and asymmetric CBS reduction as the key steps. Millpuline B (1) was synthesized with up to 94.3% enantiomeric excess and

  摘要 Millpline B ( 1 ) 分离自Millettia pulchra，是一种具有手性中心的天然生物活性化合物。在此，我们报告了使用格氏反应和不对称 CBS 还原作为关键步骤从市售的 6,7-二氢-4(5H)-苯并呋喃酮 ( 4 ) 中首次全合成 (+/-)-Millpuline B。Millpuline B ( 1 ) 以高达 94.3% 的对映体过量合成，并使用 Mosher 方法阐明关键中间体11和12的绝对构型。所有合成步骤都可以在克级上进行。
• 3-phenoxy-4-pyridazinol derivatives and herbicide composition containing the same
  申请人：Tsukamoto Yoshihisa

  公开号：US20050037925A1

  公开（公告）日：2005-02-17

  A compound represented by the formula: [wherein R 1 represents a hydrogen atom, a halogen, atom, alkyl group, etc., R 2 represents a hydrogen atom, a halogen atom, alkyl group, etc., R 3 , R 4 , R 5 , R 6 and R 7 each independently represent a hydrogen atom, a halogen atom, a substitutable alkyl group, a substitutable alkenyl group, alkynyl group, a substituteable cycloalkyl group, etc., or R 3 , R 4 , R 5 , R 6 and R 7 may form a ring which may be substituted, which is formed by the adjacent two of them with carbon atoms to which the respective substituents are bonded, m and n each independently represent 0 or 1.] a salt thereof, an ester derivative thereof and an agricultural chemical containing the same as an effective ingredient, and a herbicidal composition containing the compound and a second herbicidally active compound as effective ingredients.

  一种化合物由以下式子表示：[其中R1代表氢原子，卤素原子，烷基团等，R2代表氢原子，卤素原子，烷基团等，R3，R4，R5，R6和R7各自独立地代表氢原子，卤素原子，可替换的烷基团，可替换的烯基团，炔基团，可替换的环烷基团等，或R3，R4，R5，R6和R7可以形成一个环，该环可以被取代，该环由相邻的两个碳原子形成，这些碳原子与相应的取代基团相连，m和n各自独立地代表0或1。]其盐，酯衍生物及含有该化合物为有效成分的农药，以及含有该化合物和第二种草甘膦活性化合物为有效成分的除草剂组合物。
• 3-Phenoxy-4-pyridazinol derivatives and herbicidal composition containing the same
  申请人：Tsukamoto Yoshihisa

  公开号：US20100041555A1

  公开（公告）日：2010-02-18

  A compound represented by the formula: [wherein R 1 represents a hydrogen atom, a halogen atom, alkyl group, etc., R 2 represents a hydrogen atom, a halogen atom, alkyl group, etc., R 3 , R 4 , R 5 , R 6 and R 7 each independently represent a hydrogen atom, a halogen atom, a substitutable alkyl group, a substitutable alkenyl group, alkynyl group, a substitutable cycloalkyl group, etc., or R 3 , R 4 , R 5 , R 6 and R 7 may form a ring which may be substituted, which is formed by the adjacent two of them with carbon atoms to which the respective substituents are bonded, m and n each independently represent 0 or 1.] a salt thereof, an ester derivative thereof and an agricultural chemical containing the same as an effective ingredient, and a herbicidal composition containing the compound and a second herbicidally active compound as effective ingredients.

  一种化合物，其化学式为：[其中R1代表氢原子、卤素原子、烷基等，R2代表氢原子、卤素原子、烷基等，R3、R4、R5、R6和R7各自独立地代表氢原子、卤素原子、可替换的烷基、可替换的烯基、炔基、可替换的环烷基等，或R3、R4、R5、R6和R7可形成一个环，该环可以被取代，由它们中的相邻两个碳原子形成，各自带有相应的取代基，m和n各自独立地代表0或1。]其盐、酯衍生物和含有该化合物作为有效成分的农药，以及含有该化合物和第二种除草活性化合物作为有效成分的除草剂组合物。