ethyl 2-methoxy-5,6-dihydro-2H-pyran-6-carboxylate | 321994-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: ethyl 2-methoxy-5,6-dihydro-2H-pyran-6-carboxylate
• 英文别名: ethyl (2R,6S)-6-methoxy-3,6-dihydro-2H-pyran-2-carboxylate
• CAS: 321994-95-0
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: ZOTGPTQNWLHTNN-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-methoxy-5,6-dihydro-2H-pyran-6-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 cis-5,6-dihydro-6-(hydroxymethyl)-2-methoxy-2H-pyran
  参考文献：
  名称：

  Synthesis of unsaturated lactone moieties by asymmetric hetero Diels–Alder reactions with binaphthol-titanium complexes

  摘要：

  Natural products like ratjadone and callystatin A contain an alpha,beta -unsaturated lactone moiety which adds to the biological activity of these compounds. Here we report a rapid and practical access to lactone precursor 3 by an asymmetric hetero Diels-Alder reaction as the key step and its subsequent transformation into a suitable building block 4. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02213-9
• 作为产物：
  描述：

  乙醛酸乙酯 、 1-甲氧基-1,3-丁二烯 在 titanium(IV) isopropylate 、 (R)-1,1'-Bi-2-naphthol 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以65%的产率得到ethyl 2-methoxy-5,6-dihydro-2H-pyran-6-carboxylate
  参考文献：
  名称：

  Synthesis of unsaturated lactone moieties by asymmetric hetero Diels–Alder reactions with binaphthol-titanium complexes

  摘要：

  Natural products like ratjadone and callystatin A contain an alpha,beta -unsaturated lactone moiety which adds to the biological activity of these compounds. Here we report a rapid and practical access to lactone precursor 3 by an asymmetric hetero Diels-Alder reaction as the key step and its subsequent transformation into a suitable building block 4. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02213-9

文献信息

• DIANANE-CrIII-salen Complexes as Highly Enantioselective Catalysts for Hetero-Diels–Alder Reactions of Aldehydes with Dienes
  作者：Albrecht Berkessel、Nadine Vogl

  DOI：10.1002/ejoc.200600359

  日期：2006.11

  applied to the hetero-Diels–Alder reaction of Danishefsky’s diene with various aldehydes. The reactions afford the corresponding 2-substituted 2,3-dihydro-4H-pyran-4-ones in high yields and enantioselectivities (up to 96 % ee). The effect of different counteranions of the complex on reactivity as well as enantioselectivity has been investigated. Besides Danishefsky’s diene, reaction of the less reactive

  合成了一种以DIANANE（endo,endo-2,5-diaminonorbornane）为手性骨架的新型铬-salen配合物，并将其应用于Danishefsky's二烯与各种醛的杂Diels-Alder反应。该反应以高产率和对映选择性（高达 96% ee）得到相应的 2-取代的 2,3-二氢-4H-吡喃-4-酮。已经研究了配合物的不同抗衡阴离子对反应性和对映选择性的影响。除了Danishefsky的二烯之外，反应性较低的1-甲氧基丁二烯与苯甲醛和乙醛酸乙酯的反应也可以通过铬催化剂进行。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006）
• Total Synthesis of (+)-Ratjadone
  作者：Mathias Christmann、Ulhas Bhatt、Monika Quitschalle、Eckhard Claus、Markus Kalesse

  DOI：10.1002/1521-3773(20001201)39:23<4364::aid-anie4364>3.0.co;2-g

  日期：2000.12.1
• The First Total Synthesis of (+)-Ratjadone
  作者：Ulhas Bhatt、Mathias Christmann、Monika Quitschalle、Eckhard Claus、Markus Kalesse

  DOI：10.1021/jo005768g

  日期：2001.3.1

  The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis of structural analogues for biological target identification.