furan-2-yl(thiophen-2-yl)methanol | 77806-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: furan-2-yl(thiophen-2-yl)methanol
• CAS: 77806-74-7
• 化学式: C₉H₈O₂S
• 分子量: 180.227
• InChiKey: ZKIRRJDVJPDXNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  furan-2-yl(thiophen-2-yl)methanol 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 乙醚 为溶剂， 以42%的产率得到2-furyl-2-thienylmethane
  参考文献：
  名称：

  Nutaitis, Charles F.; Patragnoni, Richard; Goodkin, Greg, Organic Preparations and Procedures International, 1991, vol. 23, # 4, p. 403 - 412

  摘要：

  DOI：
• 作为产物：
  描述：

  糠醛 、 magnesium,2H-thiophen-2-ide,bromide 以 乙醚 为溶剂， 生成 furan-2-yl(thiophen-2-yl)methanol
  参考文献：
  名称：

  Efficient Synthesis of Bis(heterocyclyl)methanes

  摘要：

  The reaction of pyrrole/furan aldehyde with Grignard reagent and pyrrole/N-methyl pyrrole in sequence allows efficient synthesis of a number of meso-elaborated bis(heterocyclyl)methanes, which are otherwise difficult to obtain through a direct aldehyde condensation route.

  DOI：

  10.1080/00397911.2010.518330

文献信息

• A Domino Aza-Piancatelli Rearrangement/Intramolecular Diels–Alder Reaction: Stereoselective Synthesis of Octahydro-1<i>H</i>-cyclopenta[<i>cd</i>]isoindole
  作者：Shaik Gouse、Narra Rajashekar Reddy、Sundarababu Baskaran

  DOI：10.1021/acs.orglett.9b01267

  日期：2019.5.17

  an efficient one-pot method for the construction of an angularly fused 5–6–5 aza-tricyclic framework has been developed in a highly stereoselective manner. This domino reaction is a novel combination of aza-Piancatelli rearrangement and intramolecular Diels–Alder reaction, which readily furnishes hexahydro-2a,5-epoxy-cyclopenta[cd]isoindole adducts, bearing six contiguous stereogenic centers in very

  首次以高度立体选择性的方式开发了一种有效的单锅法，用于构建有角度融合的5-6-5氮杂三环骨架。该多米诺反应是氮杂-Piancatelli重排和分子内Diels-Alder反应的新颖组合，可轻松提供六氢-2a，5-环氧-环戊[ cd ]异吲哚加合物，带有六个连续的立体中心，且收率很高。BBr 3介导的氧杂桥联加合物的裂解导致八氢-1 H-环戊[ cd ]异吲哚的形成，这是gracilamine生物碱的氮杂-三环BCE核心。
• Catalytic and enantioselective oxa-Piancatelli reaction using a chiral vanadium complex
  作者：Lukas Schober、Makoto Sako、Shinobu Takizawa、Harald Gröger、Hiroaki Sasai

  DOI：10.1039/d0cc02621b

  日期：——

  An enantioselective oxa-Piancatelli reaction was established for the first time using a chiral vanadium(V) catalyst. The dual Brønsted and Lewis acid properties of the vanadium catalyst afforded 4-hydroxycyclopent-2-enone derivatives in up to 90% yields and with 93 : 7 enantiomeric ratios, as well as >20 : 1 diastereomeric ratios.

  使用手性钒（V）催化剂首次建立了对映选择性的oxa-Piancatelli反应。钒催化剂的布朗斯台德和路易斯酸的双重性质以高达90％的收率和93：7对映体比率以及> 20：1非对映体比率提供了4-羟基环戊-2-烯酮衍生物。
• Efficient synthesis of 4-hydroxycyclopentenones: dysprosium(III) triflate catalyzed Piancatelli rearrangement
  作者：David Fisher、Leoni I. Palmer、Jonathan E. Cook、Jessica E. Davis、Javier Read de Alaniz

  DOI：10.1016/j.tet.2014.03.007

  日期：2014.7

  4-Hydroxycyclopentenones represent a privileged scaffold in chemical synthesis. A dysprosium(III) trifluoromethanesulfonate catalyzed rearrangement of furylcarbinols to 4-hydroxycyclopentenones via a 4π electrocyclization has been developed. The catalytic Piancatelli rearrangement affords a single trans-diastereomer from both aryl and alkyl substituted furylcarbinols.

  4-羟基环戊烯酮代表化学合成中的一种特权支架。已开发了fluoro氟（III）三氟甲磺酸via通过4π电环化催化呋喃基甲醇重排成4-羟基环戊烯酮的方法。催化的Piancatelli重排从芳基和烷基取代的呋喃基碳氢化合物得到单一的反式非对映异构体。
• Cascade rearrangement of furylcarbinols with hydroxylamines: practical access to densely functionalized cyclopentane derivatives
  作者：Gesine K. Veits、Donald R. Wenz、Leoni I. Palmer、André H. St. Amant、Jason E. Hein、Javier Read de Alaniz

  DOI：10.1039/c5ob00944h

  日期：——

  The aza-Piancatelli rearrangement with hydroxylamines to 4-aminocyclopentenones is described. Subsequent transformations highlight the versatility of the cyclopentene scaffold and the value of the hydroxylamine in this transformation.

  描述了使用氢氧胺进行aza-Piancatelli重排反应制备4-氨基环戊酮。随后的转化突显了环戊烯骨架的多功能性以及氢氧胺在这一转化中的价值。
• A chiral cobalt(<scp>ii</scp>) complex catalyzed enantioselective aza-Piancatelli rearrangement/Diels–Alder cascade reaction
  作者：Bin Shen、Qianwen He、Shunxi Dong、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/d0sc00542h

  日期：——

  A chiral N,N′-dioxide/cobalt(II) complex catalyzed highly diastereoselective and enantioselective tandem aza-Piancatelli rearrangement/intramolecular Diels–Alder reaction has been disclosed. Various valuable hexahydro-2a,5-epoxycyclopenta[cd]isoindoles bearing six contiguous stereocenters have been obtained in good yields with excellent diastereo- and enantio-selectivities from a wide range of both

  已公开了一种手性N，N'-二氧化物/钴（II）配合物，催化高度非对映选择性和对映选择性的串联氮杂-Piancatelli重排/分子内狄尔斯-阿尔德反应。从各种现成的2-呋喃基甲醇和N-（呋喃-2）中，以良好的收率获得了具有六个非连续立体中心的高收率的各种有价值的六氢-2 a，5-环氧环戊基[ cd ]异吲哚，并具有六个连续的立体中心。-基甲基）苯胺。