(4S,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-methyloxan-2-one | 1224588-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4S,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-methyloxan-2-one
• CAS: 1224588-25-3
• 化学式: C₁₃H₂₆O₃Si
• 分子量: 258.433
• InChiKey: AEVRXNQZQQCVKO-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (4S,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-methyloxan-2-one 、 Z-homogeranyl bromide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以60%的产率得到(4S,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-[(2E,6Z)-3,7-dimethylnona-2,6-dienyl]-4-methyloxan-2-one
  参考文献：
  名称：

  Methyl 3-bromomethyl-3-butenoate as an isopentane building block for the stereoselective preparation of (S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde and (+)-faranal

  摘要：

  (S)-4-Methyl-3,6-dihydro-2H-pyran-2-carbaldehyde (3), the common intermediate in the syntheses of the C17-C27 subunit of laulimalide (4) and (+)-faranal (5), the trail pheromone of the pharaoh ant, Monomorium pharaonis, were obtained via transformation of methyl 3-bromomethyl-3-butenoate (1) into allylstannane 2 and subsequent allylation of (benzyloxy)acetaldehyde (6) in accordance with the Keck procedure as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.120
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (4S,6S)-6-(hydroxymethyl)-4-methyltetrahydro-2H-pyran-2-one 在 咪唑 作用下， 以90%的产率得到(4S,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-methyloxan-2-one
  参考文献：
  名称：

  Methyl 3-bromomethyl-3-butenoate as an isopentane building block for the stereoselective preparation of (S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde and (+)-faranal

  摘要：

  (S)-4-Methyl-3,6-dihydro-2H-pyran-2-carbaldehyde (3), the common intermediate in the syntheses of the C17-C27 subunit of laulimalide (4) and (+)-faranal (5), the trail pheromone of the pharaoh ant, Monomorium pharaonis, were obtained via transformation of methyl 3-bromomethyl-3-butenoate (1) into allylstannane 2 and subsequent allylation of (benzyloxy)acetaldehyde (6) in accordance with the Keck procedure as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.120

文献信息

• Methyl 3-bromomethyl-3-butenoate as an isopentane building block for the stereoselective preparation of (S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde and (+)-faranal
  作者：Iryna V. Mineyeva、Oleg G. Kulinkovich

  DOI：10.1016/j.tetlet.2010.01.120

  日期：2010.4

  (S)-4-Methyl-3,6-dihydro-2H-pyran-2-carbaldehyde (3), the common intermediate in the syntheses of the C17-C27 subunit of laulimalide (4) and (+)-faranal (5), the trail pheromone of the pharaoh ant, Monomorium pharaonis, were obtained via transformation of methyl 3-bromomethyl-3-butenoate (1) into allylstannane 2 and subsequent allylation of (benzyloxy)acetaldehyde (6) in accordance with the Keck procedure as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.