methyl 5-hydroxy-3-oxo-6-phenylmethoxyhexanoate | 1314788-98-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 5-hydroxy-3-oxo-6-phenylmethoxyhexanoate
• CAS: 1314788-98-1
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: JDGVTRYHHRXRQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 5-hydroxy-3-oxo-6-phenylmethoxyhexanoate 在 L-Selectride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 methyl 6-(benzyloxymethyl)-2,3-dimethyl-4-oxo tetrahydro-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

文献信息

• Diastereoselective synthesis of functionalized 2-methyltetrahydropyran-4-ones
  作者：Paul A. Clarke、Philip B. Sellars、Nimesh Mistry

  DOI：10.1016/j.tetlet.2011.05.022

  日期：2011.7

  A simple procedure for the synthesis of functionalized 2-methyl-2,3-dihydropyran-4-ones, based on the Maitland-Japp reaction, and their diastereoselective conversion into functionalized 2-methyltetrahydropyran-4-ones has been developed. This allows access to a structural unit present in a large number of biologically active natural products, and has been successfully applied to the synthesis of the molecule found in Civet cat secretion. (C) 2011 Elsevier Ltd. All rights reserved.
• A Maitland–Japp inspired synthesis of dihydropyran-4-ones and their stereoselective conversion to functionalised tetrahydropyran-4-ones
  作者：Paul A. Clarke、Philip B. Sellars、Nadiah Mad Nasir

  DOI：10.1039/c5ob00292c

  日期：——

  New variations of the Maitland–Japp reaction have been developed to enable the synthesis of dihydropyrans and tetrahydropyrans with tertiary and quaternary stereocentres, including the functionalised tetrahydropyrans in Civet and the A-ring of lasonolide A.

  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。