1,3-二氢-(1-亚甲基)异苯并呋喃 | 84666-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 中文名称: 1,3-二氢-(1-亚甲基)异苯并呋喃
• 英文名称: 1-methylene-1,3-dihydroisobenzofuran
• 英文别名: 1-Methylene-1,3-dihydroisobenzofuran；3-methylidene-1H-2-benzofuran
• CAS: 84666-75-1
• 化学式: C₉H₈O
• 分子量: 132.162
• InChiKey: PYLKQVLRIKGNEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-二氢-(1-亚甲基)异苯并呋喃 在 palladium on activated charcoal 氢气 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以0.321 g的产率得到1,3-二氢-1-甲基异苯并呋喃
  参考文献：
  名称：

  Cyclization reactions of 2-alkynylbenzyl alcohol and 2-alkynylbenzylamine derivatives promoted by tetrabutylammonium fluoride

  摘要：

  The regioselectivity of the cyclization reaction of 2-ethynylbenzyl alcohol and 2-ethynylbenzylamine derivatives promoted by TBAF was investigated. Six-membered ring derivatives were obtained from the compounds, which have a butyl group on the triple bond. Whereas five-membered ring products were afforded from the substrates having hydrogen or aromatic substituents. on the acetylene moiety. It was also concluded that both the tetrabutylammonium cation and fluoride anion were essential for the cyclization. Thus, the actual mechanism and catalytic cycle were also suggested. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00991-7
• 作为产物：
  描述：

  {2-[2-(trimethylsilyl)ethynyl]phenyl}methanol 在 四丁基氯化铵 、 silver fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 1,3-二氢-(1-亚甲基)异苯并呋喃
  参考文献：
  名称：

  Cyclization reactions of 2-alkynylbenzyl alcohol and 2-alkynylbenzylamine derivatives promoted by tetrabutylammonium fluoride

  摘要：

  The regioselectivity of the cyclization reaction of 2-ethynylbenzyl alcohol and 2-ethynylbenzylamine derivatives promoted by TBAF was investigated. Six-membered ring derivatives were obtained from the compounds, which have a butyl group on the triple bond. Whereas five-membered ring products were afforded from the substrates having hydrogen or aromatic substituents. on the acetylene moiety. It was also concluded that both the tetrabutylammonium cation and fluoride anion were essential for the cyclization. Thus, the actual mechanism and catalytic cycle were also suggested. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00991-7

文献信息

• Synthesis and catalytic activity of heterogeneous rare-earth metal catalysts coordinated with multitopic Schiff-base ligands
  作者：Yilin Sun、Guangming Wu、Dinghai Cen、Yaofeng Chen、Limin Wang

  DOI：10.1039/c2dt30763d

  日期：——

  Four multitopic Schiff-base ligand precursors were synthesized via condensation of 4,4′-diol-3,3′-diformyl-1,1′-diphenyl or 1,3,5-tris(4-hydroxy-5-formylphenyl)benzene with 2,6-diisopropylaniline or 2,6-dimethylaniline. Amine elimination reactions of Ln[N(SiMe3)2]3 (Ln = La, Nd, Sm or Y) with these multitopic ligand precursors gave ten heterogeneous rare-earth metal catalysts. These heterogeneous rare-earth metal catalysts are active for intramolecular hydroalkoxylation of alkynols, and the catalytic activities are influenced by the ligand and metal ion. The recycling experiment on the most active heterogeneous catalyst showed the catalyst has a good reusability.

  合成了四种多位点 Schiff 碱配体前体，通过 4,4′-二醇-3,3′-二福尔马基-1,1′-二苯基或 1,3,5-三(4-羟基-5-福尔马基苯基)苯与 2,6-二异丙基苯胺或 2,6-二甲基苯胺缩合反应得到。Ln[N(SiMe3)2]3 (Ln = La, Nd, Sm 或 Y) 与这些多位点配体前体的胺消除反应生成了十种异质稀土金属催化剂。这些异质稀土金属催化剂在烯醇的分子内氢醇化反应中具有活性，催化活性受到配体和金属离子的影响。对最活跃的异质催化剂进行的循环实验表明，该催化剂具有良好的可重复使用性。
• Alkyl Isobenzofurans from Phthalides; Inter and Intramolecular Diels-Alder Reactions
  作者：Sanath K. Meegalla、Russell Rodrigo

  DOI：10.1055/s-1989-27438

  日期：——

  A general procedure for the conversion of phthalides 1 to alkyl isobenzofurans 4 is described and illustrated with nine. examples. Thus, the alkylidene phthalans 3 produced from the phthalides 1 in one step are in acid catalyzed equilibrium with the. alkyl isobenzofurans 4 which are trapped in situ by dienophiles as the inter- and intramolecular Diels-Alder adducts 5-9.

  描述了一种将邻苯二甲酯1转化为烷基异苯并呋喃4的一般程序，并用九个例子进行了说明。因此，从邻苯二甲酯1一步生成的烷基苯丙烯化合物3在酸催化下与烷基异苯并呋喃4处于平衡状态，这些烷基异苯并呋喃4在适当的二烯亲合试剂的作用下被原位捕获，形成相互作用和分子内的Diels-Alder加成物5-9。
• Organothorium-Catalyzed Hydroalkoxylation/Cyclization of Alkynyl Alcohols. Scope, Mechanism, and Ancillary Ligand Effects
  作者：Stephen D. Wobser、Tobin J. Marks

  DOI：10.1021/om300881b

  日期：2013.5.13

  hydroelementation processes, and an ROH/ROD kinetic isotope effect of 0.97(0.02) is observed. The reactivity patterns, kinetics, and activation parameters are consistent with a pathway proceeding via turnover-limiting alkyne insertion into the Th–O bond, with subsequent, rapid Th–C protonolysis, regenerating the initial Th–OR species.

  带有酰胺或烷基配体的有机锡鎓络合物对炔醇的高度选择性加氢烷氧基化/环化有活性。底物包括伯醇和仲醇，以及末端和内部炔烃。与强烈结合结扎催化剂如五甲基环戊二烯（CP * = C 5我5）或“限制几何构型催化剂”（CGC =我2的Si（η 5 -Me 4 Ç 5）（吨BUN））在整个反应过程中保持可溶性，与（CGC）Th（NMe 2）2（1）比Cp * 2 Th（CH 2 TMS）具有更高的活性2（2）。使用预催化剂的[（ME 3 Si）的2 N] 2的Th [κ 2 - （Ñ，c ^）-CH 2的Si（CH 3）2 N（森达3（）] 3在加入醇的）导致沉淀底物，尽管保留了催化活性。为底物范围1包括伯和仲醇以及终端和内部炔烃。原位11 H NMR光谱监测表明，速率规律在[底物]中为零级，在[催化剂]中为第一级。伯醇和末端炔烃的速度比受空间位阻的对应物要快得多，这表明空间需求占主导地位的是加氢烷氧基化/环化过渡态。周转频率高达49ħ
• Gold(I)/Chiral Rh(III) Lewis Acid Relay Catalysis Enables Asymmetric Synthesis of Spiroketals and Spiroaminals
  作者：Jun Gong、Qian Wan、Qiang Kang

  DOI：10.1002/adsc.201800492

  日期：2018.11.5

  An efficient asymmetric cascade reaction of keto esters with alkynyl alcohols and amides was catalyzed by the combination of achiral gold(I) catalysis and chiral Rh(III) Lewis acid catalysis as asymmetric relay catalysis. The corresponding spiroketals and spiroaminals were synthesized in good yields (up to 99%), with good diastereoselectivity (up to 20:1 dr) and excellent enantioselectivity (up to

  通过非手性金（I）催化和手性Rh（III）Lewis酸催化（不对称中继催化）的结合，催化了酮酸酯与炔醇和酰胺的有效不对称级联反应。合成了相应的螺环酮和螺氨基苯胺，收率好（高达99％），非对映选择性好（高达20：1 dr），对映体选择性好（高达98％ee）。
• Regioselective synthesis of phthalans via Cu(OTf)2-catalyzed 5-exo-dig intramolecular hydroalkoxylation of 2-(ethynyl)benzyl alcohols
  作者：Chandrasekaran Praveen、Chandran Iyyappan、Paramasivan Thirumalai Perumal

  DOI：10.1016/j.tetlet.2010.07.030

  日期：2010.9

  efficient, regioselective Cu(OTf)2-catalyzed 5-exo-dig intramolecular hydroalkoxylation of 2-(ethynyl)benzyl alcohol, which provides a concise access to functionalized phthalan in high yields has been developed. A wide range of substrates possessing terminal, internal, and heteroaromatic alkynes can be efficiently transformed into the targeted phthalans. Substrates with primary, secondary, and tertiary benzyl

  一种高效，区域选择性的Cu（OTF）2催化的5-外型-挖2-（乙炔基）苄醇，它提供一个简明的访问以高收率官能phthalan的分子内hydroalkoxylation已经研制成功。具有末端，内部和杂芳族炔烃的多种底物可以有效地转化为目标邻苯二甲酸酯。具有伯，仲和叔苄醇的底物也进展良好，以高收率生产了相应的邻苯二甲酸酯。不论底物的性质如何，当区域选择性成为一个问题时，环化反应都遵循高度选择性的5- exo - dig区域化学。