3-Tert-butyl-6-methoxy-6-oxohexanoic acid | 142722-49-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-Tert-butyl-6-methoxy-6-oxohexanoic acid
• CAS: 142722-49-4
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: PVKFWQMFTCXQSV-UHFFFAOYSA-N

物化性质

• 沸点：
  313.4±15.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Tert-butyl-6-methoxy-6-oxohexanoic acid 在 4-二甲氨基吡啶 、 草酰氯 、 三氯溴甲烷 、 2-mercaptopyridine-1-oxide sodium salt 作用下， 以 四氯化碳 为溶剂， 反应 0.75h， 生成 methyl 5-bromo-4-(1',1'-dimethylethyl)pentanoate
  参考文献：
  名称：

  Stereochemistry of the reversible cyclization of .omega.-formylalkyl radicals

  摘要：

  The reactions of 6-bromo-4-(1',1'-dimethylethyl)hexanal (4), 5-bromo-3-(1',1'-dimethylethyl)pentanal (11), and 5-bromo-4-(1',1'-dimethylethyl)pentanal (17) with tributylstannane have been investigated in detail. The major products are the debrominated aldehydes and cycloalkanols which arise from the cyclization of the intermediate omega-formylalkyl radicals. The stersochemical outcome of the cyclization of these radicals is dependent on the stannane concentration. At high concentrations of stannane the cyclization is essentially irreversible with the cycloalkoxy radicals being trapped before beta-scission can occur. Under these conditions the relative amount of cis and trans cycloalkanols formed are equal to the ratio of the rate constants for the two modes of cyclization; both 4 and 17 show a small preference for trans cyclization, but 11 gives equal amounts of the two diastereomers. When the stannane concentration is lowered, the lifetime of the cycloalkoxy radicals increases allowing beta-scission to occur. Thus, the cis and trans cycloalkoxy radicals approach a thermodynamic equilibrium which is reflected in the relative yields of the cis and trans cycloalkanols.

  DOI：

  10.1021/jo00044a034
• 作为产物：
  描述：

  5-(tert-butyl)oxepan-2-one 在 jones reagent 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 3-Tert-butyl-6-methoxy-6-oxohexanoic acid
  参考文献：
  名称：

  Stereochemistry of the reversible cyclization of .omega.-formylalkyl radicals

  摘要：

  The reactions of 6-bromo-4-(1',1'-dimethylethyl)hexanal (4), 5-bromo-3-(1',1'-dimethylethyl)pentanal (11), and 5-bromo-4-(1',1'-dimethylethyl)pentanal (17) with tributylstannane have been investigated in detail. The major products are the debrominated aldehydes and cycloalkanols which arise from the cyclization of the intermediate omega-formylalkyl radicals. The stersochemical outcome of the cyclization of these radicals is dependent on the stannane concentration. At high concentrations of stannane the cyclization is essentially irreversible with the cycloalkoxy radicals being trapped before beta-scission can occur. Under these conditions the relative amount of cis and trans cycloalkanols formed are equal to the ratio of the rate constants for the two modes of cyclization; both 4 and 17 show a small preference for trans cyclization, but 11 gives equal amounts of the two diastereomers. When the stannane concentration is lowered, the lifetime of the cycloalkoxy radicals increases allowing beta-scission to occur. Thus, the cis and trans cycloalkoxy radicals approach a thermodynamic equilibrium which is reflected in the relative yields of the cis and trans cycloalkanols.

  DOI：

  10.1021/jo00044a034

文献信息

• A New Modulated Oxidative Ring Cleavage of <i>α</i>-Nitrocycloalkanones by Oxone®: Synthesis of <i>α</i>,<i>ω</i>-Dicarboxylic Acids and <i>α</i>,<i>ω</i>-Dicarboxylic Acid Monomethyl Esters
  作者：Roberto Ballini、Massimo Curini、Francesco Epifano、Maria Carla Marcotullio、Ornelio Rosati

  DOI：10.1055/s-1998-5740

  日期：1998.10

  By the appropriate choice of the reaction conditions Oxone® produces the ring cleavage of α-nitrocycloalkanones affording good yields of α,ω-dicarboxylic acids and α,ω-dicarboxylic acid monomethyl esters, respectively, regardless the ring size and/or the presence of an alkyl group as substituent.

  通过适当选择反应条件，Oxone®能够实现α-硝基环烷酮的环裂解，分别得到良好产率的α,ω-二羧酸和α,ω-二羧酸单甲酯，无论环的大小和/或是否存在烷基作为取代基。
• Stereochemistry of the reversible cyclization of .omega.-formylalkyl radicals
  作者：A. L. J. Beckwith、K. D. Raner

  DOI：10.1021/jo00044a034

  日期：1992.8

  The reactions of 6-bromo-4-(1',1'-dimethylethyl)hexanal (4), 5-bromo-3-(1',1'-dimethylethyl)pentanal (11), and 5-bromo-4-(1',1'-dimethylethyl)pentanal (17) with tributylstannane have been investigated in detail. The major products are the debrominated aldehydes and cycloalkanols which arise from the cyclization of the intermediate omega-formylalkyl radicals. The stersochemical outcome of the cyclization of these radicals is dependent on the stannane concentration. At high concentrations of stannane the cyclization is essentially irreversible with the cycloalkoxy radicals being trapped before beta-scission can occur. Under these conditions the relative amount of cis and trans cycloalkanols formed are equal to the ratio of the rate constants for the two modes of cyclization; both 4 and 17 show a small preference for trans cyclization, but 11 gives equal amounts of the two diastereomers. When the stannane concentration is lowered, the lifetime of the cycloalkoxy radicals increases allowing beta-scission to occur. Thus, the cis and trans cycloalkoxy radicals approach a thermodynamic equilibrium which is reflected in the relative yields of the cis and trans cycloalkanols.