2,3-Dihydro-5-hydroxy-6-<3-(2-hydroxymethylphenyl)-2-propenyl>benzofuran | 120694-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,3-Dihydro-5-hydroxy-6-<3-(2-hydroxymethylphenyl)-2-propenyl>benzofuran
• 英文别名: 6-<1-<2-(hydroxymethyl)phenyl>-1-propen-3-yl>-2,3-dihydro-5-benzofuranol；6-(3-(2-hydroxymethylphenyl)-trans-prop-2-enyl)-5-hydroxy-2,3-dihydrobenzofuran；5-hydroxy-6-(2-hydroxymethylcinnamyl)-2,3-dihydrobenzofuran；2,3-dihydro-5-hydroxy-6-(o-hydroxymethylcinnamyl)-benzofuran；2,3-Dihydro-6-(3-(2-hydroxymethyl)phenyl-2-propenyl)-benzofuranol；6-[(E)-3-[2-(hydroxymethyl)phenyl]prop-2-enyl]-2,3-dihydro-1-benzofuran-5-ol
• CAS: 120694-96-4
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: RRKABGWFFMSVQH-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-Dihydro-5-hydroxy-6-<3-(2-hydroxymethylphenyl)-2-propenyl>benzofuran 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 0.05h， 以49%的产率得到6-<3-<2-(hydroxymethyl)phenyl>propyl>-2,3-dihydro-5-benzofuranol
  参考文献：
  名称：

  Hammond, Milton L.; Zambias, Robert A.; Chang, Michael N., Journal of Medicinal Chemistry, 1990, vol. 33, # 3, p. 909 - 918

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二氢苯并呋喃-5-甲醛 在 aluminum oxide 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.08h， 生成 2,3-Dihydro-5-hydroxy-6-<3-(2-hydroxymethylphenyl)-2-propenyl>benzofuran
  参考文献：
  名称：

  [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
  [FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS

  摘要：

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。

  公开号：

  WO2021237371A1

文献信息

• Substituted cinnamyl-2,3-dihydrobenzofuran and analogs useful as
  申请人：Merck & Co., Inc.

  公开号：US04537903A1

  公开（公告）日：1985-08-27

  Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophilic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.

  将亚苄基-2,3-二氢苯并呋喃及类似物制备自亚苄卤代物与2,3-二氢苯并呋喃阴离子或其类似物的亲核取代反应。这些化合物被发现是有效的局部抗炎药物。
• Synthesis of 6-(3-Aryl-2-propenyl)-2,3-dihydro-5-hydroxybenzofuran Derivatives by Cross Coupling Reactions
  作者：Ramon J. Alabaster、Ian F. Cottrell、David Hands、Guy R. Humphrey、Derek J. Kennedy、Stanley H. B. Wright

  DOI：10.1055/s-1989-27329

  日期：——

  The synthesis of 6-(3-aryl-2-propenyl)-2,3-dihydro-5-hydroxybenzofuran derivatives by cross coupling between 6-bromo-2,3-dihydro-benzofurans and cinnamyl halides via organo-metallic compounds has been explored. Palladium catalysed reaction between benzofurylzinc bromides and cinnamyl acetates gave high yields of pure products, and the reaction was developed into an economic process for the large scale preparation of 2,3-dihydro-5-hydroxy-6-[3-(2-hydroxymethylphenyl)-2-propenyl]benzofuran, a topical anti-inflammatory agent.

  通过有机金属化合物，探索了6-溴-2,3-二氢苯并呋喃与肉桂基卤化物之间的交叉耦合反应，以合成6-(3-芳基-2-丙烯基)-2,3-二氢-5-羟基苯并呋喃衍生物。钯催化下，苯并呋喃锌溴化物与肉桂基乙酸酯的反应产生了高产率的纯产品，该反应已发展成经济的工艺，用于大规模制备2,3-二氢-5-羟基-6-[3-(2-羟甲基苯基)-2-丙烯基]苯并呋喃，这是一种外用抗炎剂。
• Phenylpropyl-2,3-dihydrobenzofurans useful as anti-inflammatory agents
  申请人：Merck & Co., Inc.

  公开号：US04713393A1

  公开（公告）日：1987-12-15

  Phenylalkyl-2,3-dihydrobenzofurans and analogs were prepared by (1) nucleophilic substitution involving an appropriately substituted 2,3-dihydrobenzofuranol (or 2,3-dihydrobenzopyranol) and a cinnamylhalide followed by reduction; or (2) by Wittig reaction involving a halomethyl derivative of 2,3-dihydrobenzofuran (or 2,3-dihydrobenzopyran and an aryl or a heteroaryl aldehyde followed by reduction. These compounds were found to be potent anti-inflammatory agents.

  苯基烯基-2,3-二氢苯并呋喃及其类似物是通过以下两种方法制备的：(1) 亲核取代，涉及适当取代的2,3-二氢苯并呋喃醇（或2,3-二氢苯并吡喃醇）和肉桂基卤代物的还原；或者(2) 通过Wittig反应，涉及2,3-二氢苯并呋喃（或2,3-二氢苯并吡喃）的卤甲基衍生物和芳基或杂环芳基醛的还原制备。这些化合物被发现具有强效的抗炎作用。
• Certain heterocyclic-ethyl-2,3-dihydrobenzofurans useful as
  申请人：Merck & Co., Inc.

  公开号：US04775679A1

  公开（公告）日：1988-10-04

  Phenylalkyl-2,3-dihydrobenzofurans and analogs were prepared by (1) nucleophilic substitution involving an appropriately substituted 2,3-dihydrobenzofuranol (or 2,3-dihydrobenzopyranol) and a cinnamylhalide followed by reduction; or (2) by Wittig reaction involving a halomethyl derivative of 2,3-dihydrobenzofuran (or 2,3-dihydrobenzopyran and an aryl or a heteroaryl aldehyde followed by reduction. These compounds were found to be potent anti-inflammatory agents.

  苯基烷基-2,3-二氢苯并呋喃及其类似物是通过以下两种方法制备的：(1) 通过亲核取代，涉及适当取代的2,3-二氢苯并呋喃醇（或2,3-二氢苯并吡喃醇）和肉桂基卤代物的还原; 或者(2) 通过威廉逊合成，涉及2,3-二氢苯并呋喃（或2,3-二氢苯并吡喃）的卤甲基衍生物和芳基或杂环芳基醛的还原。这些化合物被发现具有强效的抗炎作用。
• Phenylalkyl-2,3-dihydrobenzofurans and analogs useful as anti-inflammatory agents
  申请人：Merck & Co., Inc.

  公开号：EP0199235A2

  公开（公告）日：1986-10-29

  Compounds of formula (I): and pharmaceutically acceptable salts thererof are disclosed wherein m is 1 to 4; n is 2 or 3; r is 1 to 3; A is, e.g., phenyl substituted with (R')q wherein q is an integer of 1 to 5 and when there are more than one R', R' can be the same or different from each other and is hydrogen; halo; loweralkoxy; lower alkenoyl; haloloweralkyl; cyano; hydroxyloweralkyl; or hydroxy; and R, R2 and R3 independently are R'. Those compounds are prepared by (1) nucleophilic substitution involving an appropriately substituted 2,3-dihydrobenzofuranol (or 2,3-dihydrobenzopyranol) and a cinnamylhalide followed by reduction; or (2) by Wittig reaction involving a halomethyl derivative of 2,3-dihydrobenzofuran (or 2,3,-dihydroben- zopyran and an aryl or a heteroaryl aldehyde followed by reduction. These compounds were found to be potent antiinflammatory agents.

  式(I)化合物 及其药学上可接受的盐类，其中 m 为 1 至 4 n 是 2 或 3 r 为 1 至 3； A 是例如被 (R')q 取代的苯基，其中 q 是 1 至 5 的整数，当有多个 R'时，R'可以彼此相同或不同，并且是氢；卤代；低级烷氧基；低级烯酰基；卤代低级烷基；氰基；羟基低级烷基；或羟基；以及 R、R2 和 R3 独立地为 R'。这些化合物是通过以下方法制备的：(1) 2,3-二氢苯并呋喃（或 2,3-二氢苯并呋喃）与肉桂酰卤发生亲核取代反应，然后还原；或 (2) 2,3-二氢苯并呋喃（或 2,3,-二氢苯并呋喃）的卤代甲基衍生物与芳基醛或杂芳基醛发生 Wittig 反应，然后还原。这些化合物被发现是有效的抗炎剂。