(+/-)-cis-2-(2-Propenyl)-γ-octanoic Lactone | 135074-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (+/-)-cis-2-(2-Propenyl)-γ-octanoic Lactone
• 英文别名: (3R,5S)-5-butyl-3-prop-2-enyloxolan-2-one
• CAS: 135074-23-6；135074-24-7
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: JZEYQKGYJPHDHN-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-cis-2-(2-Propenyl)-γ-octanoic Lactone 在 copper(l) chloride 、 palladium dichloride 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以86%的产率得到(+/-)-cis-2-(2-Oxopropyl)-γ-octanoic Lactone
  参考文献：
  名称：

  Assigning the relative stereochemistry between C(2) and C(4) of the 2-acetonyl-4-alkylbutyrolactone substructures of the appropriate annonaceous acetogenins

  摘要：

  The relative stereochemistry between C(2) and C(4) of the naturally occurring, rearranged acetonylbutyrolactone-containing annonaceous acetogenins has been determined. Model lactones 4c, 4t, 6c, and 6t, which mimic the rearranged portion of the natural products in question, have been synthesized and unambiguously assigned as having cis or trans stereochemistry on the basis of H-1 NMR NOE experiments. Each stereoisomeric pair displays diagnostic coupling constant and chemical shift trends. These data were then compared with those of all of the pertinent acetogenins bullatacinone (2), squamone (7), isoannonacin (8), isoannonacin-10-one (9), and rollinone (10) and some of their peracetate derivatives. For none of these compounds had the C(2)/C(4) relative stereochemistry been previously determined. The major (for 2 and 10) or only reported isomers (for 7-9) bear a trans C(2)/C(4) relationship.

  DOI：

  10.1021/jo00017a018
• 作为产物：
  描述：

  (+/-)-cis and (+/-)-trans-2-(Ethoxycarbonyl)-2-(2-propenyl)-γ-octanoic Lactones 在 氢氧化钾 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 48.08h， 生成 (+/-)-cis-2-(2-Propenyl)-γ-octanoic Lactone
  参考文献：
  名称：

  Assigning the relative stereochemistry between C(2) and C(4) of the 2-acetonyl-4-alkylbutyrolactone substructures of the appropriate annonaceous acetogenins

  摘要：

  The relative stereochemistry between C(2) and C(4) of the naturally occurring, rearranged acetonylbutyrolactone-containing annonaceous acetogenins has been determined. Model lactones 4c, 4t, 6c, and 6t, which mimic the rearranged portion of the natural products in question, have been synthesized and unambiguously assigned as having cis or trans stereochemistry on the basis of H-1 NMR NOE experiments. Each stereoisomeric pair displays diagnostic coupling constant and chemical shift trends. These data were then compared with those of all of the pertinent acetogenins bullatacinone (2), squamone (7), isoannonacin (8), isoannonacin-10-one (9), and rollinone (10) and some of their peracetate derivatives. For none of these compounds had the C(2)/C(4) relative stereochemistry been previously determined. The major (for 2 and 10) or only reported isomers (for 7-9) bear a trans C(2)/C(4) relationship.

  DOI：

  10.1021/jo00017a018