l-2,3-dihydrobenzo-2-furoic acid methyl ester | 24758-34-7

• 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: l-2,3-dihydrobenzo-2-furoic acid methyl ester
• 英文别名: Methyl (2S)-2,3-dihydro-1-benzofuran-2-carboxylate
• CAS: 24758-34-7
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: MVZXFWDZKDGPHE-VIFPVBQESA-N

物化性质

• 沸点：
  180 °C(Press: 2 Torr)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  l-2,3-dihydrobenzo-2-furoic acid methyl ester 在 正丁基锂 、 jones reagent 、 zinc borohydride 、 dimsylsodium 、 二异丁基氢化铝 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 25.75h， 生成 15-(l-2,3-dihydro-2-benzufuryl)-ω-pentanorprostaglandin E₂
  参考文献：
  名称：

  Structure-activity studies of configurationally rigid arylprostaglandins

  摘要：

  Potent, albeit nonselective, smooth-muscle stimulant activity has been previously reported for 16-phenoxy- and 17-phenylprostaglandins, a finding that led to the design and development of the tissue-selective uterine stimulant sulprostone. As an extension of this work, analogues incorporating the 16-phenoxy and 17-phenyl substituents into the rigid indanyl, tetrahydronaphthyl, dihydrobenzofuryl, and dihydrobenzopyranyl ring systems were prepared and evaluated for uterine stimulant activity in vitro and diarrheal effects in vivo. Since these cyclic groups, with the exception of the indanyl, contain a chiral center, both optical antipodes were prepared. These studies demonstrate that ring size, heteroatom, and absolute configuration at C-16 are important determinants for potency and selectivity.

  DOI：

  10.1021/jm00357a004
• 作为产物：
  描述：

  苯并二氢呋喃-2-羧酸 在 硫酸 作用下， 生成 l-2,3-dihydrobenzo-2-furoic acid methyl ester
  参考文献：
  名称：

  Structure-activity studies of configurationally rigid arylprostaglandins

  摘要：

  Potent, albeit nonselective, smooth-muscle stimulant activity has been previously reported for 16-phenoxy- and 17-phenylprostaglandins, a finding that led to the design and development of the tissue-selective uterine stimulant sulprostone. As an extension of this work, analogues incorporating the 16-phenoxy and 17-phenyl substituents into the rigid indanyl, tetrahydronaphthyl, dihydrobenzofuryl, and dihydrobenzopyranyl ring systems were prepared and evaluated for uterine stimulant activity in vitro and diarrheal effects in vivo. Since these cyclic groups, with the exception of the indanyl, contain a chiral center, both optical antipodes were prepared. These studies demonstrate that ring size, heteroatom, and absolute configuration at C-16 are important determinants for potency and selectivity.

  DOI：

  10.1021/jm00357a004

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。
• Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands: Design, Synthesis, and Use in Cu-Catalyzed Inter- and Intramolecular Asymmetric O–H Insertion Reactions
  作者：Shinji Kitagaki、Shunsuke Murata、Kisaki Asaoka、Kenta Sugisaka、Chisato Mukai、Naoko Takenaga、Keisuke Yoshida

  DOI：10.1248/cpb.c18-00519

  日期：2018.10.1

  insertion reactions of α-diazo esters. The reactivities and enantioselectivities of Cu complexes of the synthesized bisoxazoline ligands were lower than those of ligands without central chirality. However, planar chiral [2.2]paracyclophane-based bisoxazoline ligands with an inserted benzene spacer that had a sterically demanding isopropyl substituent showed good enantioselectivities in inter- and intramolecular

  合成了直接连接到平面手性[2.2]对环环烷骨架上的中心手性双恶唑啉，并在Cu催化的α-重氮酯的分子间乙醇氢插入反应中将其作为不对称配体进行了评估。合成的双恶唑啉配体的Cu配合物的反应性和对映选择性低于没有中心手性的配体。然而，具有手性要求高的异丙基取代基的带有插入的苯间隔基的平面手性[2.2]对环环烷基双恶唑啉配体在分子间和分子内芳族OH插入反应中没有良好的对映选择性，而没有中心手性。
• Enantioselective Copper-Catalyzed Intramolecular Phenolic OH Bond Insertion: Synthesis of Chiral 2-Carboxy Dihydrobenzofurans, Dihydrobenzopyrans, and Tetrahydrobenzooxepines
  作者：Xiao-Guang Song、Shou-Fei Zhu、Xiu-Lan Xie、Qi-Lin Zhou

  DOI：10.1002/anie.201209455

  日期：2013.2.25

  Efficient: A copper‐catalyzed enantioselective intramolecular insertion of carbenoids into phenolic OH bonds has been developed. This method can be used for the synthesis of the title compounds in high yields and excellent enantioselectivities under mild and neutral conditions (see scheme). NaBArF=sodium tetrakis[3,5‐bis(trifluoromethyl)phenyl]borate.

  有效：一个铜催化卡宾成酚类的O对映选择性分子内插入 H键已经研制成功。该方法可用于在温和和中性条件下以高收率和出色的对映选择性合成标题化合物（参见方案）。NaBAr F =四[3,5-双（三氟甲基）苯基]硼酸钠。
• HOSOKAWA, TAKAHIRO;OKUDA, CHOZO;MURAHASHI, SHUN-ICHI, J. ORG. CHEM., 1985, 50, N 8, 1282-1287
  作者：HOSOKAWA, TAKAHIRO、OKUDA, CHOZO、MURAHASHI, SHUN-ICHI

  DOI：——

  日期：——
• US7034051B2
  申请人：——

  公开号：US7034051B2

  公开（公告）日：2006-04-25