(5-iodo-2-oxo-2H-pyran-6-yl)acetic acid | 1111219-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (5-iodo-2-oxo-2H-pyran-6-yl)acetic acid
• 英文别名: 2-(3-Iodo-6-oxopyran-2-yl)acetic acid
• CAS: 1111219-37-4
• 化学式: C₇H₅IO₄
• 分子量: 280.019
• InChiKey: GPVMJFXEBPDORO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  香叶醇 、 (5-iodo-2-oxo-2H-pyran-6-yl)acetic acid 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以2.0628 g的产率得到(2E)-3,7-dimethylocta-2,6-dienyl (5-iodo-2-oxo-2H-pyran-6-yl)acetate
  参考文献：
  名称：

  Biomimetic Synthesis toward the Transtaganolides/Basiliolides

  摘要：

  A concise biomimetic approach toward transtaganolides C and D involving an Ireland-Claisen rearrangement/intramolecular Diels-Alder reaction sequence suggesting the involvement of pericyclic reactions in the biosynthesis of these biologically active plant metabolites is presented. A final coupling reaction establishes the carbon framework of the transtaganolides.

  DOI：

  10.1021/ol802760z
• 作为产物：
  描述：

  6-(2-hydroxyethyl)-5-iodo-2H-pyran-2-one 在 高碘酸 、 pyridinium chlorochromate 作用下， 以 乙腈 为溶剂， 反应 1.33h， 生成 (5-iodo-2-oxo-2H-pyran-6-yl)acetic acid
  参考文献：
  名称：

  Biomimetic Synthesis toward the Transtaganolides/Basiliolides

  摘要：

  A concise biomimetic approach toward transtaganolides C and D involving an Ireland-Claisen rearrangement/intramolecular Diels-Alder reaction sequence suggesting the involvement of pericyclic reactions in the biosynthesis of these biologically active plant metabolites is presented. A final coupling reaction establishes the carbon framework of the transtaganolides.

  DOI：

  10.1021/ol802760z

文献信息

• The Total Syntheses of Basiliolide C, epi-Basiliolide C, and Protecting-Group-Free Total Syntheses of Transtaganolides C and D
  作者：Jonny R. Gordon、Hosea M. Nelson、Scott C. Virgil、Brian M. Stoltz

  DOI：10.1021/jo501924u

  日期：2014.10.17

  The total syntheses of basiliolide C and previously unreported epi-basiliolide C are achieved by an Ireland–Claisen/Diels–Alder cascade. The development of a palladium catalyzed cross-coupling of methoxy alkynyl zinc reagents allows for the protecting-group-free syntheses of transtaganolides C and D. Syntheses of transtaganolides C and D are accomplished in a single operation to generate three rings

  爱尔兰-克莱森/迪尔斯-阿尔德级联反应实现了巴西里立德C和以前未曾报道的上位basiliolide C的总合成。钯催化的甲氧基炔基锌试剂的交叉偶联的发展使得可以无保护基地合成塔格糖苷C和D。塔格糖苷C和D的合成可在一次操作中完成，从而生成三个环，两个全碳原子。四环中心，以及来自单环，非手性前体的四个三级立体中心。
• A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D
  作者：Hosea M. Nelson、Kei Murakami、Scott C. Virgil、Brian M. Stoltz

  DOI：10.1002/anie.201008003

  日期：2011.4.11

  In a flash: The total synthesis of transtaganolide and basiliolide natural products is achieved in three steps from achiral, monocyclic esters (see scheme). Featured in the syntheses are an Ireland‐Claisen/Diels–Alder cascade and a novel methoxyacetylide coupling/cyclization sequence.

  瞬间：由非手性单环酯（参见方案）可通过三个步骤完成反式塔果内酯和巴利希里德天然产物的总合成。合成中的特征是Ireland-Claisen / Diels-Alder级联和新颖的甲氧基乙酰胺偶联/环化序列。
• SYNTHETIC TRANSTAGANOLIDE AND BASILIOLIDE PRODUCTS, DERIVATIVES THEREOF, AND SYNTHESIS METHODS THEREOF
  申请人：Nelson Hosea

  公开号：US20120184754A1

  公开（公告）日：2012-07-19

  Compounds represented by Formula I are provided that include synthetic transtaganolide and basiliolide products. Derivatives of these compounds and methods of synthesis are also provided.

  提供了由I式表示的化合物，其中包括合成的转油酸内酯和巴西里内酯产物。还提供了这些化合物的衍生物和合成方法。
• Total Syntheses of (−)-Transtaganolide A, (+)-Transtaganolide B, (+)-Transtaganolide C, and (−)-Transtaganolide D and Biosynthetic Implications
  作者：Hosea M. Nelson、Jonny R. Gordon、Scott C. Virgil、Brian M. Stoltz

  DOI：10.1002/anie.201301212

  日期：2013.6.24

  ‘Dibal'lin’ on a budget: The enantioselective total syntheses of transtaganolides A–D are rapidly achieved by a highly diastereoselective Ireland–Claisen/Diels–Alder cascade reaction of an enantioenriched geraniol derivative (see scheme). Based on X‐ray diffraction data, the absolute configuration of these metabolites is established and discussed within the context of existing biosynthetic hypotheses

  预算中的“Dibal'lin”：通过对映体富集的香叶醇衍生物的高度非对映选择性爱尔兰-克莱森/狄尔斯-阿尔德级联反应快速实现转塔格内酯 A-D 的对映选择性全合成（参见方案）。基于 X 射线衍射数据，在现有生物合成假设的背景下建立并讨论了这些代谢物的绝对构型。
• US8912347B2
  申请人：——

  公开号：US8912347B2

  公开（公告）日：2014-12-16