methyl 5-(furan-2-yl)-5-hydroxy-3-oxopentanoate | 35468-75-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 5-(furan-2-yl)-5-hydroxy-3-oxopentanoate
• 英文别名: Methyl 5-(furan-2-yl)-5-hydroxy-3-oxopentanoate
• CAS: 35468-75-8
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: OZGMBZHGBPGWOS-UHFFFAOYSA-N

物化性质

• 沸点：
  301.3±32.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-(furan-2-yl)-5-hydroxy-3-oxopentanoate 在 吡啶 、 4-二甲氨基吡啶 、 三甲基氯硅烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.67h， 生成 methyl 4-acetoxy-6-(furan-2-yl)-2,2-dimethyl-5,6-dihydro-2H-pyran-3-carboxylate
  参考文献：
  名称：

  A Maitland–Japp inspired synthesis of dihydropyran-4-ones and their stereoselective conversion to functionalised tetrahydropyran-4-ones

  摘要：

  已开发出新的Maitland–Japp反应变体，可用于合成带有三级和四级立体中心的二氢吡喃和四氢吡喃，包括Civet中的官能化四氢吡喃和lasonolide A的A环。

  DOI：

  10.1039/c5ob00292c
• 作为产物：
  描述：

  Chan's diene 在 (S,S)-naphthyl-TADDOL 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 methyl 5-(furan-2-yl)-5-hydroxy-3-oxopentanoate
  参考文献：
  名称：

  Enantioselective vinylogous aldol reaction of Chan’s diene catalyzed by hydrogen-bonding

  摘要：

  Hydrogen-bonding activation of aromatic aldehydes by a TADDOL-derivative promotes the vinylogous aldol reaction of Chan's diene in moderate efficiency and enantioselectivity. Electron-poor aromatic aldehydes show an enhanced reactivity and a competing asymmetric hetero-Diels-Alder reaction takes place in comparable (or higher) yields and enantiomeric excesses. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.159

文献信息

• Silicon tetrachloride in organic synthesis: new applications for the vinylogous aldol reaction
  作者：Maria R. Acocella、Margherita De Rosa、Antonio Massa、Laura Palombi、Rosaria Villano、Arrigo Scettri

  DOI：10.1016/j.tet.2005.02.020

  日期：2005.4

  efficient methodology for vinylogous aldol reactions based on SiCl4 catalysis. According to the nucleophilicity Mayr's scale, vinylogous aldol reaction of Chan's diene proved to be effective by using catalytic amount of SiCl4, without any other promoter. On the contrary, the SiCl4/Lewis base system has been conveniently exploited for the efficient and selective vinylogous reaction of less nucleophilic

  本文介绍了一种基于SiCl 4催化的乙烯基醇醛醇缩醛反应的新颖而有效的方法。根据亲核性迈尔（Mayr）规模，通过使用催化量的SiCl 4而不使用任何其他助催化剂，证明了陈氏二烯的乙烯基醇醛醇缩醛反应是有效的。相反，SiCl 4 / Lewis碱系统已被方便地用于较少亲核的Danishefsky's二烯和2-三甲基甲硅烷基氧基呋喃（TMSOF）的高效选择性乙烯基反应。实际上，许多路易斯碱（例如亚砜，甲酰胺和磷酰胺）已成功用作SiCl 4发起人。由2,2,6-三甲基-[1,3]-二恶英-4-酮衍生物衍生而来的TMSOF和甲硅烷基氧二烯需要化学计量的SiCl 4，而Chan和Danishefsky的二烯的乙烯基醇醛缩合反应在存在催化或亚化学计量的催化剂。
• A Chemoenzymatic Approach to Optically Active 5-Hydroxy-3-oxo-carboxylates
  作者：Chengye Yuan、Chengfu Xu、Yonghui Zhang

  DOI：10.1055/s-2004-817746

  日期：——

  Enzymatic hydrolysis was applied to the preparation of certain chiral 5-hydroxy-3-oxo-carboxylates that are potential precursors for natural product synthesis via the formation of lactone derivatives and tetrahydropyran rings.

  酶促水解被应用于某些手性5-羟基-3-氧基羧酸酯的制备，这些化合物是通过形成内酯衍生物和四氢吡喃环用于天然产物合成的潜在前体。
• Synthesis of 2,6-trans- and 3,3,6-trisubstituted tetrahydropyran-4-ones from Maitland–Japp derived 2H-dihydropyran-4-ones: a total synthesis of diospongin B
  作者：Paul A. Clarke、Nadiah Mad Nasir、Philip B. Sellars、Alejandra M. Peter、Connor A. Lawson、James L. Burroughs

  DOI：10.1039/c6ob01182a

  日期：——

  stereoelectronic preference for pseudo-axial addition of the nucleophile and trapping of the enolate from the opposite face. Application of these methods led to a synthesis of the potent anti-osteoporotic diarylheptanoid natural product diospongin B.

  梅特兰–贾普反应的6位取代2 H-二氢吡喃-4-酮产物已转化为含有不常见取代模式的四氢吡喃。用碳亲核试剂处理6-取代的-2 H-二氢吡喃-4-酮导致形成具有2,6-反式-立体化学排列的四氢吡喃环。相同的6-取代的2 H-二氢吡喃-4-酮与L的反应-Selectride导致形成3，6-二取代的四氢吡喃环，而用碳亲电试剂捕获中间烯醇化物进而导致形成3，3，6-三取代的四氢吡喃环。新取代基的相对立体化学构型由亲核试剂的伪轴向加成和从相反面捕获烯醇化物的立体电子偏好控制。这些方法的应用导致了有效的抗骨质疏松性二芳基庚烷天然产物双皂甙B的合成。
• Synthesis of multifunctionalized building blocks via vinylogous addition of Chan’s diene to carbonyl and carbonyl-related electrophiles, mediated by molecular iodine
  作者：Rosaria Villano、Maria R. Acocella、Arrigo Scettri

  DOI：10.1016/j.tet.2011.02.036

  日期：2011.4

  The synthesis of multifunctionalized beta-ketoesters has been achieved by using molecular iodine as a catalyst under very mild conditions. The vinylogous addition of Chan's diene 1 to carbonyl and carbonyl-related compounds (aldehydes, ketones, imines and acetals) occurred with high efficiencies and with complete gamma-selectivity, giving a useful method for the synthesis of interesting libraries of different delta-functionalized beta-ketoesters. (C) 2011 Elsevier Ltd. All rights reserved.
• Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates
  作者：Chengfu Xu、Chengye Yuan

  DOI：10.1016/j.tet.2004.12.059

  日期：2005.2

  A simple and convenient method was reported for the preparation of optically active beta-hydroxy-beta-arylpropionates, delta-hydroxy-delta-aryl-beta-oxo-pentanoates and their butyryl derivatives via CRL-catalyzed hydrolysis. The optically active products are potential precursors of some chiral pharmaceuticals and natural products. (C) 2005 Elsevier Ltd. All rights reserved.