1-epi-pathylactone A | 140165-43-1

• 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: 1-epi-pathylactone A
• 英文别名: Pathylactone A；(5R,6R,7S,10R)-10-hydroxy-6,7-dimethyl-6-(2-oxopropyl)-1-oxaspiro[4.5]decan-2-one
• CAS: 140165-43-1
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: IAQWIMUGUMQBNL-FRJFDASCSA-N

物化性质

• 熔点：
  92-93 °C(Solv: heptane (142-82-5))
• 沸点：
  428.2±20.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-epi-pathylactone A 在 potassium superoxide 、 18-冠醚-6 作用下， 以 乙二醇二甲醚 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 (5S,9S,10R)-9,10-dimethyl-10-(2-oxopropyl)-1-oxaspiro[4.5]dec-6-en-2-one
  参考文献：
  名称：

  Synthesis of nor-sesquiterpene spirolactones and their steroidal hybrids revisited. The neopentyl dilemma: misassignment of one stereocentre may necessitate a completely new approach

  摘要：

  Inversion at the highly congested Cl position of 1-epi-pathylactone A (1-epi-1), or its corresponding steroidal hybrid 8a, using a diverse range of published procedures including microwave assisted Mitsunobu reaction or via oxidation to the corresponding ketone and subsequent reduction, was unsuccessful in our hands. Attempts to convert the Cl hydroxyl group into its corresponding chloride, en route to napalilactone 2a, also failed. Precursors with the Cl cc configuration installed at early stage proved not to be amenable to the targets under a broad range of conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.08.005
• 作为产物：
  描述：

  ethyl 3-((2R,3aS,7R,7aR)-7-((tert-butyldimethylsilyl)oxy)-2-methoxy-3a-methyltetrahydro-2H-spiro[benzofuran-4,2'-[1,3]dioxolan]-7a(5H)-yl)propanoate 在 palladium on activated charcoal 吡啶 、 邻苯二甲酸二甲酯 、 氢氟酸 、 potassium tert-butylate 、 氢气 、 四氯化钛 、 potassium carbonate 、 乙腈 、 calcium carbonate 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 42.33h， 生成 1-epi-pathylactone A
  参考文献：
  名称：

  Enantioselective Total Synthesis of 1-epi-Pathylactone A

  摘要：

  The first enantioselective total synthesis of 1-epi-pathylactone A, 3, has been accomplished using a PhI(OAc)(2)-mediated domino reaction as a key step. No diastereomeric separation was required throughout the whole synthetic scheme presented in this paper. Comparison of H-1 and C-13 NMR spectral data of the synthetic product with the reported spectral data of natural pathylactone A, coupled with an X-ray crystallographic analysis, led to the conclusion that the C1 configuration in the original paper was erroneously ascribed to (R).

  DOI：

  10.1021/ol070207y

文献信息

• Synthesis of nor-sesquiterpene spirolactones and their steroidal hybrids revisited. The neopentyl dilemma: misassignment of one stereocentre may necessitate a completely new approach
  作者：Imad Safir、Angeline Chanu、Zobida Elkhayat、Ramkrishna Basak、Siméon Arseniyadis

  DOI：10.1016/j.tetasy.2014.08.005

  日期：2014.10

  Inversion at the highly congested Cl position of 1-epi-pathylactone A (1-epi-1), or its corresponding steroidal hybrid 8a, using a diverse range of published procedures including microwave assisted Mitsunobu reaction or via oxidation to the corresponding ketone and subsequent reduction, was unsuccessful in our hands. Attempts to convert the Cl hydroxyl group into its corresponding chloride, en route to napalilactone 2a, also failed. Precursors with the Cl cc configuration installed at early stage proved not to be amenable to the targets under a broad range of conditions. (C) 2014 Elsevier Ltd. All rights reserved.
• Enantioselective Total Synthesis of 1-<i>epi</i>-Pathylactone A
  作者：Angéline Chanu、Imad Safir、Ramkrishna Basak、Angèle Chiaroni、Siméon Arseniyadis

  DOI：10.1021/ol070207y

  日期：2007.3.1

  The first enantioselective total synthesis of 1-epi-pathylactone A, 3, has been accomplished using a PhI(OAc)(2)-mediated domino reaction as a key step. No diastereomeric separation was required throughout the whole synthetic scheme presented in this paper. Comparison of H-1 and C-13 NMR spectral data of the synthetic product with the reported spectral data of natural pathylactone A, coupled with an X-ray crystallographic analysis, led to the conclusion that the C1 configuration in the original paper was erroneously ascribed to (R).