Methyl 5-hydroxy-3-oxo-7-phenylmethoxyheptanoate | 152419-65-3

• 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-7-phenylmethoxyheptanoate
• CAS: 152419-65-3
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: IWEYOWYRSNESSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  436.6±40.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 5-hydroxy-3-oxo-7-phenylmethoxyheptanoate 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 Pseudomonas sp. lipase 、 D(+)-10-樟脑磺酸 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 phosphate buffer 、 溶剂黄146 、 乙腈 为溶剂， 反应 55.0h， 生成 1-acetoxy-7-benzyloxy-anti-3,5-dihydroxy-3,5-O-isopropylidene-heptane
  参考文献：
  名称：

  Preparation of chiral 1,3 skipped anti- and syn-tetrols via highly enantioselective biocatalytic resolution

  摘要：

  Biocatalytic resolution of the 7-benzyloxy-3,5-anti-dioxolan-1,3 5,7-tetrol and the 7-benzyloxy-3,5-syn-dioxolan-1,3,5,7-tetrol was found to be highly enantioselective leading to differently functionalized chiral tetrols with significantly high e.e. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00467-0
• 作为产物：
  描述：

  3-苄氧基-1-丙醇 在 正丁基锂 、 sodium hydride 、 pyridinium chlorochromate 作用下， 生成 Methyl 5-hydroxy-3-oxo-7-phenylmethoxyheptanoate
  参考文献：
  名称：

  Polyhydroxylated chiral building block by enzymic desymmetrization of meso 1,3 syn diols

  摘要：

  A new seven-carbon polyhydroxylated chiral synthon is obtained, as single enantiomer, in nearly quantitative yield by enzymatic desymmetrization of the appropriate meso compound. Pseudomonas fluorescens shows an high degree of enantiotopic discrimination in a particularly complex molecule possessing a 1,3 syn diol structure; likewise, this chiral synthon has been easily transformed into a known compactin analogue.

  DOI：

  10.1021/jo00056a002

文献信息

• 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。
• 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.
• Polyhydroxylated chiral building block by enzymic desymmetrization of meso 1,3 syn diols
  作者：Carlo Bonini、Rocco Racioppi、Giuliana Righi、Licia Viggiani

  DOI：10.1021/jo00056a002

  日期：1993.2

  A new seven-carbon polyhydroxylated chiral synthon is obtained, as single enantiomer, in nearly quantitative yield by enzymatic desymmetrization of the appropriate meso compound. Pseudomonas fluorescens shows an high degree of enantiotopic discrimination in a particularly complex molecule possessing a 1,3 syn diol structure; likewise, this chiral synthon has been easily transformed into a known compactin analogue.
• Preparation of chiral 1,3 skipped anti- and syn-tetrols via highly enantioselective biocatalytic resolution
  作者：Carlo Bonini、Lucia Chiummiento、Maria Funicello

  DOI：10.1016/s0957-4166(01)00467-0

  日期：2001.10

  Biocatalytic resolution of the 7-benzyloxy-3,5-anti-dioxolan-1,3 5,7-tetrol and the 7-benzyloxy-3,5-syn-dioxolan-1,3,5,7-tetrol was found to be highly enantioselective leading to differently functionalized chiral tetrols with significantly high e.e. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Enzyme-catalyzed desymmetrization of meso-skipped polyols to useful chiral building blocks
  作者：Carlo Bonini、Rocco Racioppi、Licia Viggiani、Giuliana Righi、Leucio Rossi

  DOI：10.1016/s0957-4166(00)80117-2

  日期：1993.5

  The biocatalytic desymmetrization, in presence of different enzymes, of two models of polyfunctionalized diols in a meso form was studied PFL was found to be the most selective enzyme with excellent results in chemical and optical yield with some of the tested substrates. The obtained chiral building block was utilized for some useful synthetic transformations toward the synthesis of natural products.