(S)-2-methoxy-4-methylpentanal | 912653-89-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-methoxy-4-methylpentanal
• 英文别名: (2S)-2-methoxy-4-methylpentanal
• CAS: 912653-89-5
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: DKMGKIOQPSPEFN-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-methoxy-4-methylpentanal 在 三氟化硼乙醚 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.25h， 生成 (2S,3S,4S)-3-benzyloxy-4-methoxy-2,6-dimethylheptanal
  参考文献：
  名称：

  Stereoselective allyl transfer to chiral α-methoxycarbaldehydes: A model study related to the C-9/C-15 fragment of geldanamycin

  摘要：

  The enantiomerically pure alpha-methoxycarbaldehyde 3 was prepared from L-leucine in five steps and 31% overall yield. The aldehyde was subjected to a diastereoselective BF3-mediated crotylation with silane 4 and to various reagent-controlled addition reactions. The configuration of aldol addition products 19 and 20 was proven by single crystal X-ray crystallography. Based on these data spectral comparison allowed an unambiguous assignment of the desired anti,syn-crotylation product 2b and of the syn,syn-crotylation product 2a. Unexpectedly, product 2a of the BF3-mediated crotylation is formally the product of chelation-control. The anti, syn-crotylation product 2b, which is a model for the C-9/C-15 fragment of geldanamycin, was obtained by a reagent-controlled crotylation with the chiral (Z)-crotylborane 23. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.056
• 作为产物：
  描述：

  (S)-2-羟基-4-甲基戊酸甲酯 在 sodium hypochlorite 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 lithium aluminium tetrahydride 、 sodium hydride 、 碳酸氢钠 、 potassium bromide 作用下， 以 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (S)-2-methoxy-4-methylpentanal
  参考文献：
  名称：

  Stereoselective allyl transfer to chiral α-methoxycarbaldehydes: A model study related to the C-9/C-15 fragment of geldanamycin

  摘要：

  The enantiomerically pure alpha-methoxycarbaldehyde 3 was prepared from L-leucine in five steps and 31% overall yield. The aldehyde was subjected to a diastereoselective BF3-mediated crotylation with silane 4 and to various reagent-controlled addition reactions. The configuration of aldol addition products 19 and 20 was proven by single crystal X-ray crystallography. Based on these data spectral comparison allowed an unambiguous assignment of the desired anti,syn-crotylation product 2b and of the syn,syn-crotylation product 2a. Unexpectedly, product 2a of the BF3-mediated crotylation is formally the product of chelation-control. The anti, syn-crotylation product 2b, which is a model for the C-9/C-15 fragment of geldanamycin, was obtained by a reagent-controlled crotylation with the chiral (Z)-crotylborane 23. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.056

文献信息

• Stereoselective allyl transfer to chiral α-methoxycarbaldehydes: A model study related to the C-9/C-15 fragment of geldanamycin
  作者：T HORNEFF、E HERDTWECK、S RANDOLL、T BACH

  DOI：10.1016/j.bmc.2006.05.056

  日期：2006.9.15

  The enantiomerically pure alpha-methoxycarbaldehyde 3 was prepared from L-leucine in five steps and 31% overall yield. The aldehyde was subjected to a diastereoselective BF3-mediated crotylation with silane 4 and to various reagent-controlled addition reactions. The configuration of aldol addition products 19 and 20 was proven by single crystal X-ray crystallography. Based on these data spectral comparison allowed an unambiguous assignment of the desired anti,syn-crotylation product 2b and of the syn,syn-crotylation product 2a. Unexpectedly, product 2a of the BF3-mediated crotylation is formally the product of chelation-control. The anti, syn-crotylation product 2b, which is a model for the C-9/C-15 fragment of geldanamycin, was obtained by a reagent-controlled crotylation with the chiral (Z)-crotylborane 23. (c) 2006 Elsevier Ltd. All rights reserved.