5-(tert-butyldimethylsilanyloxy)hexanal | 112185-22-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 5-(tert-butyldimethylsilanyloxy)hexanal
• 英文别名: 5-(t-butyldimethylsilyloxy)hexanal；(+/-)-5-tert.-Butyldimethylsilyloxyhexanal；5-[Tert-butyl(dimethyl)silyl]oxyhexanal
• CAS: 112185-22-5
• 化学式: C₁₂H₂₆O₂Si
• 分子量: 230.423
• InChiKey: OOMHBCICDMXWKU-UHFFFAOYSA-N

物化性质

• 沸点：
  255.7±23.0 °C(Predicted)
• 密度：
  0.864±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  5-(tert-butyldimethylsilanyloxy)hexanal 在 吗啉 、 吡啶 、 正丁基锂 、 碘 、 potassium diazodicarboxylate 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 、 苯 为溶剂， 生成
  参考文献：
  名称：

  Total synthesis of dl-19-hydroxyprostaglandin E1 and dl-13-cis-15-epi-19-hydroxyprostaglandin E1

  摘要：

  DOI：

  10.1021/ja00487a043
• 作为产物：
  描述：

  5-酮基已腈 在 咪唑 、 sodium tetrahydroborate 、 二异丁基氢化铝 作用下， 以 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 5-(tert-butyldimethylsilanyloxy)hexanal
  参考文献：
  名称：

  Total synthesis of dl-19-hydroxyprostaglandin E1 and dl-13-cis-15-epi-19-hydroxyprostaglandin E1

  摘要：

  DOI：

  10.1021/ja00487a043

文献信息

• Preparation of t-butyl 4-diethylphosphono-3-oxobutanethioate and use in the synthesis of (E)-4-alkenyl-3-oxoesters and macrolides
  作者：Steven V. Ley、Peter R. Woodward

  DOI：10.1016/s0040-4039(00)95725-3

  日期：1987.1

  The preparation of t-butyl 4-diethylphosphono-3-oxobutanethioate (1) and Wadsworth- Emmons reaction with aldehydes and ketones is reported. Some of the products of these reactions were converted to unsaturated 3-oxomacrolides or 3-oxodiolides by transesterification in the presence of copper-(I)-trifluoroacetate.

  报道了4-二乙基膦酰基-3-氧代丁硫醇叔丁基酯的制备（1）和与醛和酮的Wadsworth-Emmons反应。在铜-（I）-三氟乙酸铜的存在下，通过酯交换反应将这些反应的一些产物转化为不饱和的3-氧代大环内酯或3-氧代环氧乙烷。
• Effect of Methyl Substituents on the Double Bond Involved in the Formation of Tetrahydropyrans from Hydroxy Allylic Acetates
  作者：Masaya Nakata、Minoru Yasuda、Jin Kawakita

  DOI：10.1246/bcsj.67.2607

  日期：1994.9

  acetates by an internal secondary hydroxyl group under acidic conditions to yield 2,6-disubstituted tetrahydropyrans has been investigated. The reaction is influenced by the substitution type of the double bond.

  已经研究了在酸性条件下通过内部仲羟基取代烯丙基乙酸酯环化以产生 2,6-二取代的四氢吡喃。该反应受双键取代类型的影响。
• Total Synthesis of (±)-Zearalanone
  作者：Franz Bracher、Jürgen Krauss

  DOI：10.1007/s007060170067

  日期：2001.7

   A new approach to the macrocyclic lactone zearalanone is described utilizing an alkenol and an arene trifluoromethanesulfonate as starting materials. The key step is a Pd(0)-catalyzed cross-coupling of the arene trifluoromethanesulfonate with a 9-alkyl-9-borabicyclo[3.3.1]nonane derived from the alkenol. The title compound is obtained by macrolactonization of a hydroxy acid under Mitsunobu conditions

   描述了一种新的大环内酯齐拉丙酮的制备方法，该方法以烯醇和芳烃三氟甲磺酸盐为原料。关键步骤是芳烃三氟甲磺酸酯与衍生自烯醇的9-烷基-9-硼环[3.3.1]壬烷的Pd（0）催化交叉偶联。通过在 Mitsunobu 条件下羟基酸的大环内酯化获得标题化合物 。
• Preparation of β-ketomacrolactones and β-ketodiolides using S-t-butyl 3-oxobutanethioate and S-t-butyl 4-diethylphosphono-3-oxobutanethioate
  作者：Paul M. Booth、Howard B. Broughton、Mark J. Ford、Christina M.J. Fox、Steven V. Ley、Alexandra M.Z. Slawin、David J. Williams、Peter R. Woodward

  DOI：10.1016/s0040-4020(01)89218-8

  日期：1989.1
• <i>N</i>-(17-Phosphonooxylinolenoyl)glutamine and <i>N</i>-(17-phosphonooxylinoleoyl)glutamine from Insect Gut:  The First Backbone-Phosphorylated Fatty Acid Derivatives in Nature
  作者：Dieter Spiteller、Neil J. Oldham、Wilhelm Boland

  DOI：10.1021/jo035382g

  日期：2004.2.1

  N-(17-Phosphonooxylinolenoyl)glutamine (1) and N-(17-phosphonooxylinoleoyl)glutamine (2) were isolated from the regurgitate of Spodoptora exigua and identified as the first natural alkyl chain-phosphorylated fatty acid derivatives. The compounds were characterized by HPLC-MS/MS and the assigned structures confirmed by synthesis via a dissymmetric bis-Wittig approach as the key reaction. Rearing of the larvae on a diet enriched with inorganic phosphate increased the amount of the phosphorylated N-acyl glutamines in the regurgitate.