5-deuterio-pentan-2-one | 35300-12-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-deuterio-pentan-2-one
• 英文别名: 5-Deuteriopentan-2-one
• CAS: 35300-12-0
• 化学式: C₅H₁₀O
• 分子量: 87.1259
• InChiKey: XNLICIUVMPYHGG-MICDWDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-溴-2-戊酮 在 CuI*P(n-Bu)3 、 三丁基膦 、 重水 、 naphthalen-1-yl-lithium 作用下， 生成 5-deuterio-pentan-2-one
  参考文献：
  名称：

  Direct formation and subsequent substitution of remote ketone-functionalized organocopper reagents

  摘要：

  Remote ketone-functionalized aryl- and alkylcopper reagents have been synthesized by the use of a highly activated form of zero-valent copper. 5-Bromo-2-pentanone and 4-iodobenzophenone undergo oxidative addition with activated copper to form 5-cuprio-2-pentanone and 4-cupriobenzophenone, respectively. These, in turn, can be cross-coupled with alkyl halides to produce the corresponding alkylated ketones and with acid chlorides to form the corresponding diketones. By use of this methodology, a two-step, one-pot synthesis of methyl (E)-9-oxo-2-decenoate and 8-nonen-2-one have been achieved. The former compound is the methyl ester of the ''queen substance'' of the honey bee, and the latter is part of an ''attractant mixture'' for cheese mites found in cheddar cheese. These syntheses were accomplished by converting commercially available 6-bromo-2-hexanone to 6-cuprio-2-hexanone followed by cross-coupling with commercially available methyl 4-bromocrotonate and allyl bromide, respectively.

  DOI：

  10.1021/jo00015a032

文献信息

• Direct formation and subsequent substitution of remote ketone-functionalized organocopper reagents
  作者：Greg W. Ebert、Walter R. Klein

  DOI：10.1021/jo00015a032

  日期：1991.7

  Remote ketone-functionalized aryl- and alkylcopper reagents have been synthesized by the use of a highly activated form of zero-valent copper. 5-Bromo-2-pentanone and 4-iodobenzophenone undergo oxidative addition with activated copper to form 5-cuprio-2-pentanone and 4-cupriobenzophenone, respectively. These, in turn, can be cross-coupled with alkyl halides to produce the corresponding alkylated ketones and with acid chlorides to form the corresponding diketones. By use of this methodology, a two-step, one-pot synthesis of methyl (E)-9-oxo-2-decenoate and 8-nonen-2-one have been achieved. The former compound is the methyl ester of the ''queen substance'' of the honey bee, and the latter is part of an ''attractant mixture'' for cheese mites found in cheddar cheese. These syntheses were accomplished by converting commercially available 6-bromo-2-hexanone to 6-cuprio-2-hexanone followed by cross-coupling with commercially available methyl 4-bromocrotonate and allyl bromide, respectively.