(+/-)-1-(2-furyl)but-3-en-1-yl acetate | 24334-29-0

• 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: (+/-)-1-(2-furyl)but-3-en-1-yl acetate
• 英文别名: 1-(2-furyl)but-3-en-1-yl acetate；1-(2-furyl)-3-butenyl acetate；1--but-3-enyl-acetat；1-(Fur-2-yl)-but-3-enyl-acetat；1-(2-Furyl)-3-butene-1-yl acetate；1-(furan-2-yl)but-3-enyl acetate
• CAS: 24334-29-0
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: QHZMBJOQUONRJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(2-furyl)but-3-en-1-yl acetate 在 phosphate buffer 、 PLE lipase 作用下， 反应 4.5h， 生成 (S)-1-(2-furyl)but-3-en-1-yl acetate 、 (R)-(+)-1-(2-furyl)but-3-en-1-yl acetate
  参考文献：
  名称：

  Conformational control on remote stereochemistry in the intramolecular Pauson–Khand reactions of enynes tethered to homoallyl and homopropargyl alcohols

  摘要：

  An intramolecular Pauson-Khand reaction of enynes derived from homoallyl and homopropargyl alcohols is described. 2-Furyl substituted homoallyl and homopropargyl alcohols are easily and efficiently resolved through enzymatic resolution in a high ee (93-99%) with a known stereochemistry. Each enantiomerically enriched enyne affords the conformationally most stable diastereomeric cyclopenta[c]pyran ring system. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.012
• 作为产物：
  描述：

  糠醛 在 吡啶 、 氯化铵 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 (+/-)-1-(2-furyl)but-3-en-1-yl acetate
  参考文献：
  名称：

  Study on the coupling of acyclic esters with alkenes – the synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide

  摘要：

  在以 HMPA 和 H2O 为添加剂的烯丙基溴化铵存在下，前所未有地实现了脂肪族无环酯与烯烃之间的自由基环化。这种级联自由基环化-环-开环-阴离子环化的方法可以方便有效地从现有材料中获得 2-（2-羟基烷基）环丙醇。

  DOI：

  10.1039/c2cc34630c

文献信息

• Chemoenzymatic synthesis of optically active heterocyclic homoallylic and homopropargylic alcohols
  作者：Satwinder Singh、Subodh Kumar、Swapandeep Singh Chimni

  DOI：10.1016/s0957-4166(02)00743-7

  日期：2002.12

  A chemoenzymatic methodology has been developed using indium-mediated allylation of heterocyclic aldehydes under aqueous conditions followed by Pseudomonas cepacia lipase-catalyzed enantioselective acylation of racemic homoallylic and homopropargylic alcohols in organic media. It is observed that the lipase immobilized on ceramic particles (PS-C Amano II) catalyzes the resolution in a highly enantioselective

  已开发出一种化学酶学方法，该方法是在水性介质中使用铟介导的杂环醛的烯丙基化烯丙基化，然后在有机介质中假单胞菌cepcia脂肪酶催化外消旋均烯丙基和均炔丙醇的对映选择性酰化。观察到，与天然酶（PS Amano）相比，固定在陶瓷颗粒上的脂肪酶（PS-C Amano II）以更少的时间以高对映选择性的方式催化拆分。该方法提供了新的功能化手性合成子，可用于合成天然和假天然产物。
• High Atom Efficiency in Sc(OTf)3-Catalyzed Allylation of Aldehydes with Tetraallyltin
  作者：Yoshifumi Nagano、Akihiro Orita、Junzo Otera

  DOI：10.1002/adsc.200202207

  日期：2003.5

  The high atom efficiency was achieved through addition of Ac2O in the Sc(OTf)3-catalyzed allylation of aldehyde with tetraallytin in a 4 : 1 molar ratio.

  通过在Sc（OTf）3催化的醛与四烯丙基锡的烯丙基化反应中以4：1的摩尔比添加Ac 2 O，可以实现高原子效率。
• Indium-mediated one-pot, three-component synthesis of homoallyl alcohol esters without catalysts and dehydrants
  作者：Zhengyin Du、Yanchun Li、Fen Wang、Wanwei Zhou、Jin-Xian Wang

  DOI：10.1016/j.tetlet.2010.01.092

  日期：2010.3

  Indium-mediated one-pot esterification reaction of acyl chlorides or anhydride by using in situ-prepared homoallyl alcohols from aromatic aldehydes and allyl bromide proceeded smoothly to afford the corresponding homoallyl alcohol esters in high yields within about 1 h, which provided a simple and efficient protocol for the simultaneous allylation and esterification of aldehydes without other catalysts and dehydrants

  使用芳族醛和烯丙基溴原位制备的均烯丙基醇进行的铟介导的酰氯或酸酐的一锅酯化反应可顺利进行，从而在约1小时内以高收率得到相应的均烯丙基醇酯，这提供了一种简单而有效的方法在不使用其他催化剂和脱水剂的情况下同时进行醛的烯丙基化和酯化的操作规程。
• Conformational control on remote stereochemistry in the intramolecular Pauson–Khand reactions of enynes tethered to homoallyl and homopropargyl alcohols
  作者：Serdar Sezer、Devrim Özdemirhan、Ertan Şahin、Cihangir Tanyeli

  DOI：10.1016/j.tetasy.2006.11.012

  日期：2006.11

  An intramolecular Pauson-Khand reaction of enynes derived from homoallyl and homopropargyl alcohols is described. 2-Furyl substituted homoallyl and homopropargyl alcohols are easily and efficiently resolved through enzymatic resolution in a high ee (93-99%) with a known stereochemistry. Each enantiomerically enriched enyne affords the conformationally most stable diastereomeric cyclopenta[c]pyran ring system. (c) 2006 Elsevier Ltd. All rights reserved.
• Study on the coupling of acyclic esters with alkenes – the synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide
  作者：Yawei Tu、Liejin Zhou、Ruifeng Yin、Xin Lv、Robert A. Flowers II、Kimberly A. Choquette、Huili Liu、Qingsheng Niu、Xiaoxia Wang

  DOI：10.1039/c2cc34630c

  日期：——

  The radical cyclization between aliphatic acyclic esters and alkenes was achieved unprecedentedly in the presence of allylsamarium bromide with HMPA and H2O as additives. The cascade radical cyclization–ring-opening–anionic cyclization allowed facile and efficient access to 2-(2-hydroxyalkyl)cyclopropanols from readily available materials.

  在以 HMPA 和 H2O 为添加剂的烯丙基溴化铵存在下，前所未有地实现了脂肪族无环酯与烯烃之间的自由基环化。这种级联自由基环化-环-开环-阴离子环化的方法可以方便有效地从现有材料中获得 2-（2-羟基烷基）环丙醇。