1-(benzofuran-2-yl)propan-1-ol | 220087-23-0

• 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: 1-(benzofuran-2-yl)propan-1-ol
• 英文别名: 1-benzofuran-2-yl-propan-1-ol；1-(1-benzofuran-2-yl)propan-1-ol
• CAS: 220087-23-0
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: MQOQWAWXUCJNOP-UHFFFAOYSA-N

物化性质

• 沸点：
  149 °C(Press: 12 Torr)
• 密度：
  1.116 g/cm3(Temp: 14 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  1-(benzofuran-2-yl)propan-1-ol 在 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 1-(benzofuran-2-yl)propan-1-one
  参考文献：
  名称：

  Stereoselective reduction of .gamma.-oxobutanoic acids using DIBAL-H and zinc chloride

  摘要：

  A variety of gamma-aromatic gamma-ketobutanoic acids can be reduced selectively, under optimized conditions, by the use of DIBAL-H and ZnCl2 to provide the (RS,SR)-gamma-aryl-gamma-hydroxy-beta-methylbutanoic acids. Further evidence has been gathered to support the hypothesis that the reaction proceeds by formation of a seven-membered ring complex with the aluminium or zinc atom bridging the ketone and carboxyl groups which preceeds the reduction step and that this templated reduction accounts for observed high diastereoselectivity. Also we have shown that some gamma-aryl-gamma-butyrolactones can be easily transformed via an oxidative cleavage of the aromatic ring to provide selective synthesis of either cis- or trans-tetrahydro-3-methyl-5-oxo-2-furancarboxylic acid derivatives.

  DOI：

  10.1021/jo00009a030
• 作为产物：
  描述：

  1-苯并呋喃-2-羰酰氯 生成 1-(benzofuran-2-yl)propan-1-ol
  参考文献：
  名称：

  Normant, Annales de Chimie (Cachan, France), 1942, vol. <11> 17, p. 335,346

  摘要：

  DOI：

文献信息

• Pd/C mediated synthesis of 2-substituted benzo[b]furans/nitrobenzo[b]furans in water
  作者：Manojit Pal、Venkataraman Subramanian、Koteswar Rao Yeleswarapu

  DOI：10.1016/j.tetlet.2003.09.080

  日期：2003.11

  ns in water has been accomplished via Pd/C catalyzed reaction of o-iodophenols with terminal alkynes in the presence of PPh3, CuI and prolinol. This method can tolerate a variety of functional groups present in the alkynes as well as base labile nitro group in the o-iodophenols. The protocol does not require the use of a phase transfer catalyst or water-soluble phosphine ligands and is free from the

  2-烷基/芳基取代的苯并[一种高效合成b ]呋喃/硝基苯并[ b / C]水呋喃已经经由钯而完成催化反应ö与PPH的存在末端炔烃-iodophenols 3，碘化亚铜和脯氨醇。该方法可以耐受炔烃中存在的各种官能团以及邻碘苯酚中的碱不稳定的硝基。该方案不需要使用相转移催化剂或水溶性膦配体，并且无需使用任何有机助溶剂。
• Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Ethers: Enantioselective Synthesis of Diarylethanes
  作者：Buck L. H. Taylor、Elizabeth C. Swift、Joshua D. Waetzig、Elizabeth R. Jarvo

  DOI：10.1021/ja108547u

  日期：2011.1.26

  Secondary benzylic ethers undergo stereospecific substitution reactions with Grignard reagents in the presence of nickel catalysts. Reactions proceed with inversion of configuration and high stereochemical fidelity. This reaction allows for facile enantioselective synthesis of biologically active diarylethanes from readily available optically enriched carbinols.

  二级苄基醚在镍催化剂存在下与格氏试剂发生立体有择取代反应。反应以构型反转和高立体化学保真度进行。该反应允许从容易获得的光学富集的甲醇中轻松对映选择性合成具有生物活性的二芳基乙烷。
• Acid Catalyzed Ring Transformation of Benzofurans to Tri- and Tetrasubstituted Furans
  作者：Seema Dhiman、S. S. V. Ramasastry

  DOI：10.1021/jo4018233

  日期：2013.10.18

  catalyzed benzofuran ring opening and furan ring closure sequence for the formation of tri- and tetrasubstituted furans is presented. Benzofuranyl carbinols and 1,3-dicarbonyls in the presence of a catalytic amount of an acid generated functionalized, polysubstituted furans in good to excellent yields via an unusual benzofuran ring opening and furan recyclization process. This reaction is found to be general

  提出了一种不寻常的布朗斯台德酸催化的苯并呋喃开环和呋喃环闭合序列，用于形成三和四取代的呋喃。苯并呋喃基甲醇和1,3-二羰基化合物在催化量的酸存在下，通过不寻常的苯并呋喃开环和呋喃再循环过程以良好至极好的收率生成了官能化的多取代呋喃。发现该反应即使在呋喃基甲醇上也很普遍；但是，它以中等收率产生了重排的多取代呋喃。
• Enantioselectivity of Some 1-(Benzofuran-2-y1)1-(1-<i>H</i>-imidazol-1-yl) Alkanes as Inhibitors of P450Arom
  作者：G Ali Khodarahmi、H John Smith、Paul J Nicholls、Masoud Ahmadi

  DOI：10.1111/j.2042-7158.1998.tb03352.x

  日期：2011.4.12

  The low stereospecificity of the enantiomers of 1-[(benzofuran-2-yl)-4-chlorophenyl-methyl]imidazole (6, R = H, R’ = 4′-Cl) and the corresponding 4-fluoro compound as inhibitors of aromatase (P450Arom) has been explored using 1-(5,7-dichlorobenzofuran-2-yl)-1-(1H-imidaz-1-yl)ethane (7, R1=R2 = Cl, R = CH3), -propane (7, R1=R2 = Cl, R = C2H5), and the corresponding 5,7-dibromo compounds resolved as their dibenzoyl-D (or -L) tartrates.

  Low enantioselectivity ratios of 4.8 (5,7-diCl) and 12.6 (5,7-diBr) were shown for the ethanes. The values for the corresponding propanes were 8.3 and 5.2, respectively, and for these compounds the stereoselectivity was reversed.

  摘要：研究了1-[(苯并呋喃-2-基)-4-氯苯基甲基]咪唑（6，R = H，R’ = 4'-Cl）及其相应的4-氟化合物作为芳香化酶（P450Arom）抑制剂的对映体的低立体选择性，使用1-(5,7-二氯苯并呋喃-2-基)-1-(1H-咪唑-1-基)乙烷（7，R1 = R2 = Cl，R = CH3），-丙烷（7，R1 = R2 = Cl，R = C2H5），并将相应的5,7-二溴化合物解析为它们的二苯甲酰-D（或-L）酒石酸盐。乙烷的低对映选择性比为4.8（5,7-二氯）和12.6（5,7-二溴）。相应丙烷的值分别为8.3和5.2，对于这些化合物，立体选择性是相反的。
• Normant, Annales de Chimie (Cachan, France), 1942, vol. <11> 17, p. 335,346
  作者：Normant

  DOI：——

  日期：——