2-methyl-3-(2-methylallyl)-<1,4>naphthoquinone | 69843-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methyl-3-(2-methylallyl)-<1,4>naphthoquinone
• 英文别名: 2-Methallyl-3-methylnaphthoquinon-1,4；2-Methyl-3-(2-methylprop-2-enyl)naphthalene-1,4-dione；2-methyl-3-(2-methylprop-2-enyl)naphthalene-1,4-dione
• CAS: 69843-55-6
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: ADPQNFRYYDDBAP-UHFFFAOYSA-N

物化性质

• 沸点：
  352.4±42.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(2-methylallyl)-<1,4>naphthoquinone 在 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 26.0h， 以86%的产率得到2-methyl-3-(2-oxopropyl)-<1,4>naphthoquinone
  参考文献：
  名称：

  Attachment of Ketide Side Chains on Methyl-1,4-naphthoquinones for biomimetic type angucycline syntheses

  摘要：

  The Michael addition of nucleophiles 5-10 derived from beta-ketoesters with the methyl-1,4-naphthoquinones 16 and 20 was systematically investigated in connection with a biomimetic type synthesis of angucyclinone antibiotics. Drawbacks of these reactions were the formation of regioisomers (e.g. 12/13 and 18/19), unwanted cyclizations (14 and 15), and occasional 1,2-addition (23). No side reactions and a good overall yield (80%) in the attachment of a C-3-2-oxoside chain was achieved by Stille reaction of allyl stannane 11 with the bromoquinone 24 followed by cleavage of the double bond to yield ketone 26.

  DOI：

  10.1002/prac.19973390123
• 作为产物：
  描述：

  2-溴-3-甲基萘-1,4-二酮 、 甲基烯丙基三正丁基锡 在 四(三苯基膦)钯 copper(I) bromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以93%的产率得到2-methyl-3-(2-methylallyl)-<1,4>naphthoquinone
  参考文献：
  名称：

  Attachment of Ketide Side Chains on Methyl-1,4-naphthoquinones for biomimetic type angucycline syntheses

  摘要：

  The Michael addition of nucleophiles 5-10 derived from beta-ketoesters with the methyl-1,4-naphthoquinones 16 and 20 was systematically investigated in connection with a biomimetic type synthesis of angucyclinone antibiotics. Drawbacks of these reactions were the formation of regioisomers (e.g. 12/13 and 18/19), unwanted cyclizations (14 and 15), and occasional 1,2-addition (23). No side reactions and a good overall yield (80%) in the attachment of a C-3-2-oxoside chain was achieved by Stille reaction of allyl stannane 11 with the bromoquinone 24 followed by cleavage of the double bond to yield ketone 26.

  DOI：

  10.1002/prac.19973390123

文献信息

• Attachment of Ketide Side Chains on Methyl-1,4-naphthoquinones for biomimetic type angucycline syntheses
  作者：K. Krohn、N. Böker

  DOI：10.1002/prac.19973390123

  日期：——

  The Michael addition of nucleophiles 5-10 derived from beta-ketoesters with the methyl-1,4-naphthoquinones 16 and 20 was systematically investigated in connection with a biomimetic type synthesis of angucyclinone antibiotics. Drawbacks of these reactions were the formation of regioisomers (e.g. 12/13 and 18/19), unwanted cyclizations (14 and 15), and occasional 1,2-addition (23). No side reactions and a good overall yield (80%) in the attachment of a C-3-2-oxoside chain was achieved by Stille reaction of allyl stannane 11 with the bromoquinone 24 followed by cleavage of the double bond to yield ketone 26.