(S)-2-(4-Methoxy-benzyloxy)-heptanal | 180722-69-4

• 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: (S)-2-(4-Methoxy-benzyloxy)-heptanal
• 英文别名: Heptanal, 2-[(4-methoxyphenyl)methoxy]-, (2S)-；(2S)-2-[(4-methoxyphenyl)methoxy]heptanal
• CAS: 180722-69-4
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: WCIHCKYWBLYDOD-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (1-重氮基-2-氧代丙基)膦酸二甲酯 、 (S)-2-(4-Methoxy-benzyloxy)-heptanal 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以80%的产率得到(S)-1-methoxy-4-[(oct-1-yn-3-yloxy)methyl]benzene
  参考文献：
  名称：

  醛合成炔烃的进一步改进

  摘要：

  报道了一种由醛合成炔烃的非常方便的方法。该程序采用了一种新的原位制备二甲基重氮甲基膦酸盐的方法。因此，现在可以使用市售试剂，从而避免了早期协议的缺点。简单的一锅法避免使用强碱、低温和惰性气体技术。

  DOI：

  10.1055/s-2003-44346
• 作为产物：
  描述：

  (R)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl (S)-2-(4'''-methoxybenzyloxy)heptanamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(1R)-N-[(2-methylpropan-2-yl)oxy]-1-naphthalen-1-ylethanamine
  参考文献：
  名称：

  Alkylation and aldol reactions of acyl derivatives of N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine: asymmetric synthesis of α-alkoxy-, α-substituted-β-alkoxy- and α,β-dialkoxyaldehydes

  摘要：

  Treatment of a range of O-protected glycolate derivatives of the chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine with KHMDS in the presence of 18-crown-6 followed by addition of an alkyl halide generates alpha-substituted derivatives with very high levels of diastereoselectivity. Alternatively, reaction of the potassium enolate of a propanoate or O-protected glycolate derivative of N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine with a range of aldehydes gives syn-aldol products with high levels of diastereoselectivity. These adducts may be reductively cleaved with LiAlH(4) to give enantiopure alpha-alkoxy-, alpha-substituted-beta-alkoxy- and alpha,beta-dialkoxyaldehydes in good yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.105

文献信息

• Alkylation and aldol reactions of acyl derivatives of N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine: asymmetric synthesis of α-alkoxy-, α-substituted-β-alkoxy- and α,β-dialkoxyaldehydes
  作者：Alexander N. Chernega、Stephen G. Davies、Ai M. Fletcher、Christopher J. Goodwin、David Hepworth、R. Shyam Prasad、Paul M. Roberts、Edward D. Savory、Andrew D. Smith、James E. Thomson

  DOI：10.1016/j.tet.2010.03.105

  日期：2010.6

  Treatment of a range of O-protected glycolate derivatives of the chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine with KHMDS in the presence of 18-crown-6 followed by addition of an alkyl halide generates alpha-substituted derivatives with very high levels of diastereoselectivity. Alternatively, reaction of the potassium enolate of a propanoate or O-protected glycolate derivative of N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine with a range of aldehydes gives syn-aldol products with high levels of diastereoselectivity. These adducts may be reductively cleaved with LiAlH(4) to give enantiopure alpha-alkoxy-, alpha-substituted-beta-alkoxy- and alpha,beta-dialkoxyaldehydes in good yield. (C) 2010 Elsevier Ltd. All rights reserved.
• Further Improvements of the Synthesis of Alkynes from Aldehydes
  作者：Gerald Roth、Bernd Liepold、Stephan Müller、Hans Bestmann

  DOI：10.1055/s-2003-44346

  日期：——

  A highly convenient way to perform the synthesis of alkynes from aldehydes is reported. The procedure utilizes a new in situ preparation of dimethyldiazomethylphosphonate. As a consequence a commercially available reagentcan now be used, circumventing a disadvantage of earlier protocols. The easy one-pot procedure avoids the use of strong bases, low temperatures and inert gas techniques.

  报道了一种由醛合成炔烃的非常方便的方法。该程序采用了一种新的原位制备二甲基重氮甲基膦酸盐的方法。因此，现在可以使用市售试剂，从而避免了早期协议的缺点。简单的一锅法避免使用强碱、低温和惰性气体技术。