rac-1-(benzofuran-2-yl)but-3-en-1-ol | 91324-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: rac-1-(benzofuran-2-yl)but-3-en-1-ol
• 英文别名: 1-(2-benzofuryl)-3-buten-1-ol；1-(2-benzofuryl)but-3-en-1-ol；1-(1-Benzofuran-2-yl)but-3-en-1-ol
• CAS: 91324-09-3
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: YUUOEMPHISJOIT-UHFFFAOYSA-N

物化性质

• 沸点：
  308.6±27.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  rac-1-(benzofuran-2-yl)but-3-en-1-ol 在 Lipozyme IM 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 74.5h， 生成 (-)-2-(1-(allyloxy)but-3-enyl)benzofuran
  参考文献：
  名称：

  Stereoselective synthesis of benzofuran and benzothiophene substituted dihydropyran derivatives via ring closing metathesis

  摘要：

  Ring closing metathesis reactions have been applied to diene and enyne systems derived from homoallylic alcohol backbones are described. The key intermediates 2-benzofuranyl la and 2-benzothiophenyl lb substituted homoallylic alcohols were synthesized from their corresponding carboxaldehyde derivatives. Racemic 2-heteroaryl-substituted homoallylic alcohols are successfully resolved to give the corresponding enantiopure acetates and alcohols with 80-99% ee through enzymatic resolution by various lipases. Enantiomerically enriched diene and enyne skeletons derived from homoallylic alcohols were subjected to the ring closing metathesis via first and second generation Grubbs' catalysts and the corresponding chiral heteroaryl-substituted dihydropyran derivatives were obtained with good yields (41-96%). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.08.005
• 作为产物：
  描述：

  2-苯并呋喃甲醇 在 氢氧化钾 、 potassium tert-butylate 、 四乙基溴化铵 作用下， 以 二甲基亚砜 为溶剂， 反应 7.25h， 生成 rac-1-(benzofuran-2-yl)but-3-en-1-ol
  参考文献：
  名称：

  Isomerization of 2-(allyloxymethyl)benzofurans and -benzothiophenes in the presence of potassium tert-butylate

  摘要：

  DOI：

  10.1007/bf00529578

文献信息

• Synthesis and biological evaluation of α,β-unsaturated lactones as potent immunosuppressive agents
  作者：Sun-Mi Lee、Won-Gil Lee、Young-Chul Kim、Hyojin Ko

  DOI：10.1016/j.bmcl.2011.08.020

  日期：2011.10

  Compounds having α,β-unsaturated lactones display a variety of biological activities. Many research groups have tested both natural and unnatural α,β-unsaturated lactones for as-yet undiscovered biological properties. We synthesized α,β-unsaturated lactones with various substituents at the δ-position and studied their immunosuppressive effects, that is, the inhibition of Interleukin-2 (IL-2) production

  具有α，β-不饱和内酯的化合物表现出多种生物活性。许多研究小组已经对天然和非天然α，β-不饱和内酯进行了测试，但尚未发现其生物学特性。我们合成了在δ位具有各种取代基的α，β-不饱和内酯，并研究了它们的免疫抑制作用，即抑制白介素2（IL-2）的产生。在合成的化合物中，苯并呋喃取代的α，β-不饱和内酯4h在Jurkat e6-1 T淋巴细胞（IC 50  = 66.9 nM）中表现出对IL-2产生的最佳抑制活性，而在10μM时无细胞毒性。结果表明4h 可能用作有效的免疫抑制剂，以及与IL-2相关的研究。
• Design, stereoselective synthesis and computational calculations of novel hybrid compounds via Pauson-Khand reactions
  作者：Selçuk Gümüş、Nezir Aslan、Nalan Nuriye Büyükadalı、Ayşegül Gümüş

  DOI：10.1016/j.tetasy.2017.02.014

  日期：2017.3

  A series of novel chiral hybrid compounds between benzofuran and bicyclic cyclopentenone and also benzothiophene and bicyclic cyclopentenone have been designed and synthesized. Chiral enynes derived from enantiomerically enriched homoallyl and homopropargyl alcohols were converted into bicyclic cyclopentenone structures by intramolecular Pauson-Khand reactions. This strategy provides a facile access to various bicyclic cyclopentenones substituted with benzofuran or benzothiophene ring systems in good yields. In addition to the experimental work, the ground state geometries of the hybrid compounds were optimized using Density Functional Theory applications at the B3LYP/6-31G(d,p) level in order to obtain information about the 3D geometries and electronic structure. (C) 2017 Elsevier Ltd. All rights reserved.
• Mozhaeva, L.V.; Shabanova, S.V.; Kazennova, N.B., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 766 - 769
  作者：Mozhaeva, L.V.、Shabanova, S.V.、Kazennova, N.B.、Anisimov, A.V.、Viktorova, E.A.

  DOI：——

  日期：——
• MOZHAEVA, L. V.;SHABANOVA, S. KAZENNOVA, N. B.;ANISIMOV, A. V.;VIKTOROVA,+, ZH. ORGAN. XIMII, 1984, 20, N 4, 842-845
  作者：MOZHAEVA, L. V.、SHABANOVA, S. KAZENNOVA, N. B.、ANISIMOV, A. V.、VIKTOROVA,+

  DOI：——

  日期：——
• Stereoselective synthesis of benzofuran and benzothiophene substituted dihydropyran derivatives via ring closing metathesis
  作者：Nalan Nuriye Büyükadalı、Nezir Aslan、Selçuk Gümüş、Ayşegül Gümüş

  DOI：10.1016/j.tetasy.2016.08.005

  日期：2016.10

  Ring closing metathesis reactions have been applied to diene and enyne systems derived from homoallylic alcohol backbones are described. The key intermediates 2-benzofuranyl la and 2-benzothiophenyl lb substituted homoallylic alcohols were synthesized from their corresponding carboxaldehyde derivatives. Racemic 2-heteroaryl-substituted homoallylic alcohols are successfully resolved to give the corresponding enantiopure acetates and alcohols with 80-99% ee through enzymatic resolution by various lipases. Enantiomerically enriched diene and enyne skeletons derived from homoallylic alcohols were subjected to the ring closing metathesis via first and second generation Grubbs' catalysts and the corresponding chiral heteroaryl-substituted dihydropyran derivatives were obtained with good yields (41-96%). (C) 2016 Elsevier Ltd. All rights reserved.