2,3-dihydrobenzofuran-2(R)-carboxylic acid | 77341-31-2

• 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-dihydrobenzofuran-2(R)-carboxylic acid
• 英文别名: d-2,3-dihydrobenzo-2-furoic acid；(R)-2,3-dihydro-benzofuran-2-carboxylic acid；(R)-2,3-Dihydro-benzofuran-2-carbonsaeure；(R)-2,3-dihydro-benzofuran-2-carboxylic acid；(R)-2,3-Dihydrobenzofuran-2-carboxylic acid；(2R)-2,3-dihydro-1-benzofuran-2-carboxylic acid
• CAS: 77341-31-2
• 化学式: C₉H₈O₃
• 分子量: 164.161
• InChiKey: WEVFUSSJCGAVOH-MRVPVSSYSA-N

物化性质

• 熔点：
  104-105 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  340.5±31.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  2,3-dihydrobenzofuran-2(R)-carboxylic acid 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 氢气 、 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 溶剂黄146 、 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (R)-5-(propanesulfonylamino-methyl)-2,3-dihydro-benzofuran-2-carboxylic acid-{2-[(S)-3-hydroxy-pyrrolidin-1-yl]-(S)-1-phenyl-ethyl}-methyl-amide
  参考文献：
  名称：

  Potent and highly selective kappa opioid receptor agonists incorporating chroman- and 2,3-dihydrobenzofuran-based constraints

  摘要：

  Two novel chemical classes of kappa opioid receptor agonists, chroman-2-carboxamide derivatives and 2,3-dihydrobenzofuran-2-carboxamide derivatives, were synthesized. These agents exhibited high and selective affinity for the kappa opioid receptor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.094
• 作为产物：
  描述：

  苯并二氢呋喃-2-羧酸 生成 2,3-dihydrobenzofuran-2(R)-carboxylic acid
  参考文献：
  名称：

  Fredga; Vazquez de Castro y Sarmiento, Arkiv foer Kemi, 1954, vol. 7, p. 387,388, 389

  摘要：

  DOI：

文献信息

• Fused bicyclic carboxamide derivatives and methods of their use
  申请人：Dolle E. Roland

  公开号：US20050054630A1

  公开（公告）日：2005-03-10

  Fused bicyclic carboxamide derivatives are disclosed. Pharmaceutical compositions containing the compounds and methods for their use are also disclosed.

  揭示了融合的双环羧酰胺衍生物。还公开了含有这些化合物的药物组合物以及它们的使用方法。
• THE SYNTHESES AND ABSOLUTE CONFIGURATIONS OF FOMANNOXIN, (−)-5-ACETYL-2-(1-HYDROXYMETHYLVINYL)-2,3-DIHYDROBENZOFURAN, AND ANODENDROIC ACID
  作者：Yoshiyuki Kawase、Seiji Yamaguchi、Osamu Inoue、Michiko Sannomiya、Kazuko Kawabe

  DOI：10.1246/cl.1980.1581

  日期：1980.12.5

  The title compounds were synthesized from (−)-(S)- or (+)-(R)-2,3-dihydrobenzofuran-2-carboxylic acid. And their absolute configurations were determined.

  标题化合物由(-)-(S)-或(+)-(R)-2,3-二氢苯并呋喃-2-羧酸合成。并且确定了它们的绝对构型。
• Comparison of Deacylation Rates of Chymotryptic Catalysis within an Enantiomeric Pair of p-Nitrophenyl Esters.
  作者：Kazutaka TANIZAWA、Hiroyuki YAMADA、Kunihiko ITOH、Yuichi KANAOKA

  DOI：10.1248/cpb.39.2748

  日期：——

  p-Nitrophenyl esters carrying a chiral acyl group were synthesized. These compounds were shown to meet the requirements of chymotrypsin for the specific binding and the acylation. Therefore, the behavior of p-nitrophenyl esters with chymotrypsin is considered to be virtually identical to that of p-amidinophenyl esters with trypsin which were proposed as "inverse substrates" for the enzyme. These esters, derived from each pair of enantiomers, have been successfully used for the analysis of enantiomeric preference of chymotrypsin at the deacylation stage. The chiral requirement of the enzyme active site for the catalytic efficiency was discussed.

  合成了带有手性酰基的对硝基苯基酯。这些化合物被证明符合胰蛋白酶在特定结合和酰化方面的要求。因此，认为对硝基苯基酯与胰蛋白酶的作用几乎与对氨基苯基酯与胰酶的作用相同，后者被提议作为该酶的“逆底物”。这些酯源自每对对映体，已成功用于分析胰蛋白酶在去酰化阶段的对映体偏好。讨论了酶活性位点对催化效率的手性需求。
• Fredga; Vazquez de Castro y Sarmiento, Arkiv foer Kemi, 1954, vol. 7, p. 387,388, 389
  作者：Fredga、Vazquez de Castro y Sarmiento

  DOI：——

  日期：——
• Boronic Acid Derivatives
  申请人：Merck Patent GmbH

  公开号：US20210317145A1

  公开（公告）日：2021-10-14

  α-Amino boronic acid derivatives are useful for inhibiting the activity of immunoproteasome (LMP7) and for the treatment and/or prevention of a medical condition affected by immunoproteasome activity, such as an inflammatory and autoimmune disease, a neurodegenerative disease, a proliferative disease, and cancer.