2-(4-methoxyphenyl)-2,3-dihydrobenzofuran | 140423-65-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(4-methoxyphenyl)-2,3-dihydrobenzofuran
• 英文别名: 2-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran
• CAS: 140423-65-0
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: VAWVWTFEBFXKGH-UHFFFAOYSA-N

物化性质

• 沸点：
  340.8±31.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-bromo-2-((trimethylsilyl)methyl)benzene 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 2-(4-methoxyphenyl)-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Efficient One-Pot Synthesis of 2-Aryldihydrobenzofuran

  摘要：

  以相应的羰基化合物和(2-溴苄基)三甲基硅烷为原料,通过一锅法苄基化-取代反应成功合成了一系列2-芳基二氢苯并呋喃衍生物。

  DOI：

  10.1055/s-2005-871940

文献信息

• Enantioselective Oxy-Heck-Matsuda Arylations: Expeditious Synthesis of Dihydrobenzofuran Systems and Total Synthesis of the Neolignan (−)-Conocarpan
  作者：Allan R. Silva、Ellen C. Polo、Nelson C. Martins、Carlos Roque D. Correia

  DOI：10.1002/adsc.201701278

  日期：2018.1.17

  process is demonstrated by a concise total synthesis of the neolignan (−)‐conocarpan. X‐ray diffraction of an advanced brominated intermediate in the route to (−)‐conocarpan has allowed the unequivocal assignment of the absolute stereochemistry of the oxy‐Heck–Matsuda aryldihydrobenzofuran products. A rationale for the mechanism operating in these enantioselective oxy‐Heck–Matsuda reactions is also presented

  这项工作公开了使用多种苯乙烯烯烃生成手性二氢苯并呋喃的有效对映选择性氧-Heck-Matsuda反应的第一个实例。该反应以中等至良好的产率进行，具有高反式使用N，N-配体嘧啶-双恶唑啉（PyriBox）在90:10的对映选择性中具有非对映选择性（高达20：1）。oxy-Heck-Matsuda反应在温和的条件下和较低的催化剂载量下进行。新木脂素（-）-角果胶的简明全合成证明了该方法的可行性和实用性。在通往（-）-香柏树醇的途径中，对高级溴化中间体进行X射线衍射分析，使得对氧-赫克-松田芳基二氢苯并呋喃产品的绝对立体化学的明确分配成为可能。还介绍了在这些对映选择性氧-Heck-Matsuda反应中起作用的机理的基本原理。
• Ruthenium NHC Catalyzed Highly Asymmetric Hydrogenation of Benzofurans
  作者：Nuria Ortega、Slawomir Urban、Bernhard Beiring、Frank Glorius

  DOI：10.1002/anie.201107811

  日期：2012.2.13

  H2‐O‐T! Aromatic O‐heterocycles are a challenging substrates for asymmetric hydrogenation (H2). An in situ formed chiral N‐heterocyclic carbene (NHC) ruthenium complex allows the high yielding, completely regioselective, and highly asymmetric hydrogenation of substituted benzofurans at room Temperature, giving valuable 2,3‐dihydrobenzofurans (see scheme).

  H 2 ‐O‐T！芳族O杂环是不对称氢化（H 2）的具有挑战性的底物。原位形成的手性N-杂环卡宾（NHC）钌络合物可在T温度下以高收率，完全区域选择性和高度不对称氢化取代苯并呋喃，得到有价值的2,3-二氢苯并呋喃（参见方案）。
• Ambident Effect of a <i>p</i>-Sulfinyl Group for the Introduction of Two Carbon Substituents to Phenol Rings:  A Convergent Synthesis of Diverse Benzofuran Neolignans
  作者：Shuji Akai、Nobuyoshi Morita、Kiyosei Iio、Yuka Nakamura、Yasuyuki Kita

  DOI：10.1021/ol0001261

  日期：2000.7.1

  A convergent synthesis of diversely substituted benzofuran neolignans (8) is described employing a single p-sulfinyl group on the phenols (3) as an ambident functional group for two types of carbon-carbon bond-forming reactions: (i) the direct synthesis of the dihydrobenzofuran skeletons through an aromatic Pummerer-type reaction and (ii) the ipso-substitution of the sulfur functional group by carbon

  描述了采用多种方式取代的苯并呋喃新木聚糖（8）的收敛合成方法，该方法利用酚（3）上的单个对亚磺酰基作为环境官能团，用于两种类型的碳-碳键形成反应：（i）直接合成二氢苯并呋喃骨架通过芳族Pummerer型反应和（ii）硫官能团通过碳取代基通过配体交换反应进行ipso取代。
• One-pot synthesis of substituted indoles via titanium(iv) alkoxide mediated imine formation – copper-catalyzed N-arylation
  作者：Ferdinand S. Melkonyan、Daniil E. Kuznetsov、Marina A. Yurovskaya、Alexander V. Karchava

  DOI：10.1039/c3ra40389k

  日期：——

  Readily accessible o-bromobenzylketones and primary alkyl amines and anilines were used for the construction of substituted indoles in good to excellent yields. The sequence involves a titanium-mediated reaction of ketones with amines to afford imines and subsequent intramolecular cyclization into indoles employing copper catalysis. The two-step protocol allows for the preparation of indoles bearing

  易于获得的邻溴苄基酮，伯烷基胺和苯胺以良好或优异的产率用于构建取代的吲哚。该序列涉及酮与胺的钛介导的反应以提供亚胺，并随后利用铜催化将分子内环化成吲哚。两步方案允许制备带有N-烷基和N-芳基基团的吲哚以及N-未取代的吲哚，而无需分离中间体，并且具有广泛的功能性。
• A Regioselective Lithiation of ortho-Cresols Using the Bis(dimethylamino)phosphoryl Group as a Directing Group: General Synthesis of 2,3-Dihydrobenzo(b)furans Including Naturally Occurring Neolignans.
  作者：Mituaki WATANABE、Kenji KAWANISHI、Ryuji AKIYOSHI、Sunao FURUKAWA

  DOI：10.1248/cpb.39.3123

  日期：——

  A general synthetic method was developed for 2-aryl-2, 3-dihydrobenzo[b]furans via regioselective lithiation of ortho-tolyl tetramethylphosphorodiamidates followed by addition of aromatic aldehydes as a key step. ortho-Tolyl tetramethylphosphorodiamidates were regioselectively lithiated with sec-BuLi in tetrahydrofuran at -105°C to give benzylic lithio species. The resulting lithio species were reacted with aromatic aldehydes to provide 1, 2-diarylethanolderivatives. Reductive removal of the phosphoryl group with lithium aluminum hydride followed by acidic treatment led to 2-aryl-2, 3-dihydrobenzo[b]furans in good overall yields. The utility of this strategy was demonstrated in regioselective syntheses of highly substituted neolignan natural products, such as (±)-licarin B and (±)-carnatol, starting from O-bis(dimethylamino)phosphorylated eugenol or isoeugenol.

  作为关键步骤，通过对原甲苯基四甲基磷二酰胺进行区域选择性石化作用，然后加入芳香醛，开发了一种 2-芳基-2，3-二氢苯并[b]呋喃的通用合成方法。生成的二硫代锂与芳香醛反应，得到 1，2-二硫代乙醇衍生物。用氢化铝锂还原去除磷基，然后进行酸处理，可得到 2-芳基-2，3-二氢苯并[b]呋喃，总产率很高。在以 O-双（二甲基氨基）磷酸化丁香酚或异丁香酚为起始物，对 (±)-licarin B 和 (±)-carnatol 等高度取代的新木犀草素天然产物进行区域选择性合成时，证明了这一策略的实用性。