(3R,4R)-4-((4-methoxybenzyl)oxy)-3-methylpentan-2-one | 1428737-98-7

• 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: (3R,4R)-4-((4-methoxybenzyl)oxy)-3-methylpentan-2-one
• 英文别名: (3R,4R)-4-[(4-methoxyphenyl)methoxy]-3-methylpentan-2-one
• CAS: 1428737-98-7
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: GPPSOPUKAYKWLT-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4-((4-methoxybenzyl)oxy)-3-methylpentan-2-one 在 2,6-二甲基吡啶 、 四(三苯基膦)钯 、 氯代二环己基硼烷 、 sodium hexamethyldisilazane 、 potassium carbonate 、 戴斯-马丁氧化剂 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 32.0h， 生成 tributyl [(4R,5S,7S,8S,E)-5,7,9-tris(tert-butyldimethylsilyloxy)-1-methylene-3,4,8-trimethyl-2-nonen-1-yl]stannane
  参考文献：
  名称：

  Synthesis of the C-1–C-17 Fragment of Amphidinolides C, C2, C3, and F

  摘要：

  The C-1-C-17 fragment of amphidinolides C, C2, C3, and F has been constructed from a trans-2,5-disubstituted dihydrofuranone prepared by diastereoselective rearrangement of a free or metal-bound oxonium ylide generated from a metal carbenoid. The dihydrofuranone was converted into an aldehyde corresponding to the C-1-C-8 framework, and this was coupled to the C-9-C-17 unit by nucleophilic addition of a vinylic anion.

  DOI：

  10.1021/ol4004838
• 作为产物：
  描述：

  (2S,4R,5R)-5-hydroxy-4-methyl-3-oxohexan-2-yl benzoate 在 锂硼氢 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 23.87h， 生成 (3R,4R)-4-((4-methoxybenzyl)oxy)-3-methylpentan-2-one
  参考文献：
  名称：

  Synthesis of the C(7)-C(20) Fragment of Spirotoamides A, B and C

  摘要：

  This work describes the preparation of the C(7)-C(20) fragment of spirotoamides A to C in a very elegant fashion, achievement very high levels of stereocontrol. The synthesis has been accomplished by a sequence involving 14 steps (0.36% overall yield, average of 81% for each step) in high diastereo and enantioselectivity, employing, as determining steps, asymmetric Mukaiyama and boron-mediated 1,5-anti promoted aldol reactions between alpha-methyl-beta-hydroxyketones and aldehydes.

  DOI：

  10.21577/0103-5053.20190126

文献信息

• Synthesis of the C-1–C-17 Fragment of Amphidinolides C, C2, C3, and F
  作者：J. Stephen Clark、Guang Yang、Andrew P. Osnowski

  DOI：10.1021/ol4004838

  日期：2013.4.5

  The C-1-C-17 fragment of amphidinolides C, C2, C3, and F has been constructed from a trans-2,5-disubstituted dihydrofuranone prepared by diastereoselective rearrangement of a free or metal-bound oxonium ylide generated from a metal carbenoid. The dihydrofuranone was converted into an aldehyde corresponding to the C-1-C-8 framework, and this was coupled to the C-9-C-17 unit by nucleophilic addition of a vinylic anion.
• Synthesis of the C(7)-C(20) Fragment of Spirotoamides A, B and C
  作者：Allan Rossini、Luiz Dias

  DOI：10.21577/0103-5053.20190126

  日期：——

  This work describes the preparation of the C(7)-C(20) fragment of spirotoamides A to C in a very elegant fashion, achievement very high levels of stereocontrol. The synthesis has been accomplished by a sequence involving 14 steps (0.36% overall yield, average of 81% for each step) in high diastereo and enantioselectivity, employing, as determining steps, asymmetric Mukaiyama and boron-mediated 1,5-anti promoted aldol reactions between alpha-methyl-beta-hydroxyketones and aldehydes.