methyl 3-hydroxy-2,4-dimethylpent-4-enoate | 606489-56-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 3-hydroxy-2,4-dimethylpent-4-enoate
• 英文别名: Methyl-3-hydroxy-2,4-dimethyl-1,4-pentenoat
• CAS: 606489-56-9
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: KXKXNCOMNMEEBL-UHFFFAOYSA-N

物化性质

• 沸点：
  225.0±20.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-hydroxy-2,4-dimethylpent-4-enoate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到methyl 2,4-dimethyl-3-oxopent-4-enoate
  参考文献：
  名称：

  莫能菌素 A 的倒数第二个生物合成三烯中间体的合成

  摘要：

  Synthese de l'acide (dihydroxy-5,7 dioxo-9,25ethyl-16 heptamethyl-2,4,6,12,18,22,24 methoxy-3) hexacosatriene-12,16,20oique par copulation de 3 synthons希罗

  DOI：

  10.1021/ja00275a055
• 作为产物：
  描述：

  2-甲基丙烯醛 、 丙酸甲酯 在 lithium diisopropyl amide 作用下， 生成 methyl 3-hydroxy-2,4-dimethylpent-4-enoate
  参考文献：
  名称：

  Regiochemically and stereochemically defined synthesis of allylsilanes

  摘要：

  Allyl sulfides containing a siloxy or hydroxy group at appropriate positions were successfully converted by two methods into two types of allylsilanes with almost complete stereo- and regiocontrol. In one method, an allyllithium was generated from the siloxy compound after which the silyl group migrated from oxygen to the carbanionic site. The reaction of 4-[[(trimethylsilyl)oxy]methyl]-3-methyl-2-cyclohexenyl phenyl sulfide with lithium di-tert-butylbiphenylide (LDBB) led to an exclusive formation of (1R*,2R*)-2-methyl-2-(trimethylsilyl)-3-cyclohexene-1-methanol. The second method involved the silylation of an oxyanion-carbanion. Using this method, (1R*,4R*)-1-methyl-4-(trimethylsilyl)-2-cyclohexene-1-methanol was obtained by treating its lithium alkoxide with LDBB followed by silylation with chlorotrimethylsilane.

  DOI：

  10.1021/ja00073a018

文献信息

• Synthesis of the proposed penultimate biosynthetic triene intermediate of monensin A
  作者：Dinesh V. Patel、Frank. VanMiddlesworth、John. Donaubauer、Peter. Gannett、Charles J. Sih

  DOI：10.1021/ja00275a055

  日期：1986.7

  Synthese de l'acide (dihydroxy-5,7 dioxo-9,25 ethyl-16 heptamethyl-2,4,6,12,18,22,24 methoxy-3) hexacosatriene-12,16,20oique par copulation de 3 synthons chiraux

  Synthese de l'acide (dihydroxy-5,7 dioxo-9,25ethyl-16 heptamethyl-2,4,6,12,18,22,24 methoxy-3) hexacosatriene-12,16,20oique par copulation de 3 synthons希罗
• Regiochemically and stereochemically defined synthesis of allylsilanes
  作者：Shinji Marumoto、Isao Kuwajima

  DOI：10.1021/ja00073a018

  日期：1993.10

  Allyl sulfides containing a siloxy or hydroxy group at appropriate positions were successfully converted by two methods into two types of allylsilanes with almost complete stereo- and regiocontrol. In one method, an allyllithium was generated from the siloxy compound after which the silyl group migrated from oxygen to the carbanionic site. The reaction of 4-[[(trimethylsilyl)oxy]methyl]-3-methyl-2-cyclohexenyl phenyl sulfide with lithium di-tert-butylbiphenylide (LDBB) led to an exclusive formation of (1R*,2R*)-2-methyl-2-(trimethylsilyl)-3-cyclohexene-1-methanol. The second method involved the silylation of an oxyanion-carbanion. Using this method, (1R*,4R*)-1-methyl-4-(trimethylsilyl)-2-cyclohexene-1-methanol was obtained by treating its lithium alkoxide with LDBB followed by silylation with chlorotrimethylsilane.