3,4-didehydro-7-isopropyl-4-methyl-2-oxepanone | 122865-17-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4-didehydro-7-isopropyl-4-methyl-2-oxepanone
• 英文别名: 5-methyl-2-propan-2-yl-3,4-dihydro-2H-oxepin-7-one
• CAS: 122865-17-2
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: WUTQBVVPTSQHQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  3,4-didehydro-7-isopropyl-4-methyl-2-oxepanone 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 为溶剂， 反应 30.0h， 以18%的产率得到4,5-didehydro-7-isopropyl-4-methyl-2-oxepanone
  参考文献：
  名称：

  DBU-Catalyzed Deconjugation of 7-Substituted 3,4-Didehydro-2-oxepanones. Deuterium Incorporation, Significance of the Imine Double Bond, and Application to the Synthesis of a Key Pharmacophore

  摘要：

  7-Substituted 3,4-Didehydro-2-oxepanones are conveniently deconjugated to the 4,5-didehydro derivatives by DBU. The isomerization of 7-benzyl-substituted 2-oxepanones proceeds to the extent of 90% over the initial 3 h; the concentration falls gradually thereafter to achieve, in 25 h, a 3:2 equilibrium in favor of deconjugation. Such an equilibrium does not exist for the 7-methyl and the 7-(2-phenethyl) derivatives. The significance of the imine double bond in DBU has been explored. The isomerization in CDCl3 causes deuterium incorporation at positions 3 and 5 of the 2-oxepanones examined and at position 6 of DBU. The mechanistic rationales for these deuterium incorporations are advanced. The transformation of 7-benzyl-3,4-didehydro-2-oxepanone into a bicyclo[3.3.0] skeleton that is present in a diverse class of biologically active natural products is described as a possible potential use of the present deconjugation methodology.

  DOI：

  10.1021/jo971417z
• 作为产物：
  描述：

  6-羟基-3,7-二甲基辛酸内酯 在 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 3,4-didehydro-7-isopropyl-4-methyl-2-oxepanone
  参考文献：
  名称：

  DBU-Catalyzed Deconjugation of 7-Substituted 3,4-Didehydro-2-oxepanones. Deuterium Incorporation, Significance of the Imine Double Bond, and Application to the Synthesis of a Key Pharmacophore

  摘要：

  7-Substituted 3,4-Didehydro-2-oxepanones are conveniently deconjugated to the 4,5-didehydro derivatives by DBU. The isomerization of 7-benzyl-substituted 2-oxepanones proceeds to the extent of 90% over the initial 3 h; the concentration falls gradually thereafter to achieve, in 25 h, a 3:2 equilibrium in favor of deconjugation. Such an equilibrium does not exist for the 7-methyl and the 7-(2-phenethyl) derivatives. The significance of the imine double bond in DBU has been explored. The isomerization in CDCl3 causes deuterium incorporation at positions 3 and 5 of the 2-oxepanones examined and at position 6 of DBU. The mechanistic rationales for these deuterium incorporations are advanced. The transformation of 7-benzyl-3,4-didehydro-2-oxepanone into a bicyclo[3.3.0] skeleton that is present in a diverse class of biologically active natural products is described as a possible potential use of the present deconjugation methodology.

  DOI：

  10.1021/jo971417z

文献信息

• TATEBA, HIDEKI;MIHARA, SATORU, AGR. AND BIOL. CHEM. , 54,(1990) N, C. 2271-2276
  作者：TATEBA, HIDEKI、MIHARA, SATORU

  DOI：——

  日期：——
• Tateba, Hideki; Mihara, Satoru, Agricultural and Biological Chemistry, 1990, vol. 54, # 9, p. 2271 - 2276
  作者：Tateba, Hideki、Mihara, Satoru

  DOI：——

  日期：——
• DBU-Catalyzed Deconjugation of 7-Substituted 3,4-Didehydro-2-oxepanones. Deuterium Incorporation, Significance of the Imine Double Bond, and Application to the Synthesis of a Key Pharmacophore
  作者：Duraiswamy A. Jeyaraj、Kamal K. Kapoor、Veejendra K. Yadav、Harsh M. Gauniyal、Masood Parvez

  DOI：10.1021/jo971417z

  日期：1998.1.1

  7-Substituted 3,4-Didehydro-2-oxepanones are conveniently deconjugated to the 4,5-didehydro derivatives by DBU. The isomerization of 7-benzyl-substituted 2-oxepanones proceeds to the extent of 90% over the initial 3 h; the concentration falls gradually thereafter to achieve, in 25 h, a 3:2 equilibrium in favor of deconjugation. Such an equilibrium does not exist for the 7-methyl and the 7-(2-phenethyl) derivatives. The significance of the imine double bond in DBU has been explored. The isomerization in CDCl3 causes deuterium incorporation at positions 3 and 5 of the 2-oxepanones examined and at position 6 of DBU. The mechanistic rationales for these deuterium incorporations are advanced. The transformation of 7-benzyl-3,4-didehydro-2-oxepanone into a bicyclo[3.3.0] skeleton that is present in a diverse class of biologically active natural products is described as a possible potential use of the present deconjugation methodology.