methyl 6-hydroxy-4-oxohexanoate | 1214750-14-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 6-hydroxy-4-oxohexanoate
• CAS: 1214750-14-7
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: RYBCRANHOBOLIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  276.3±15.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  11.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 6-hydroxy-4-oxohexanoate 在 吡啶 、 1,2,2,6,6-五甲基哌啶 、 咪唑 、 盐酸 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 正丁基锂 、 三甲基氯硅烷 、 lithium hydroxide monohydrate 、 二碳酸二叔丁酯 、 间氯过氧苯甲酸 、 三(邻甲基苯基)磷 、 sodium iodide 、 三甲基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 62.08h， 生成 2-(6-oxo-9,9-divinyl-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetic acid
  参考文献：
  名称：

  Total Syntheses of Leuconoxine, Leuconodine B, and Melodinine E by Oxidative Cyclic Aminal Formation and Diastereoselective Ring-Closing Metathesis

  摘要：

  Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.

  DOI：

  10.1021/ol500903e
• 作为产物：
  描述：

  1,4-环己二酮 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl 6-hydroxy-4-oxohexanoate
  参考文献：
  名称：

  Total Syntheses of Leuconoxine, Leuconodine B, and Melodinine E by Oxidative Cyclic Aminal Formation and Diastereoselective Ring-Closing Metathesis

  摘要：

  Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.

  DOI：

  10.1021/ol500903e

文献信息

• Total Synthesis of (+)-Fendleridine (Aspidoalbidine) and (+)-1-Acetylaspidoalbidine
  作者：Erica L. Campbell、Andrea M. Zuhl、Christopher M. Liu、Dale L. Boger

  DOI：10.1021/ja908819q

  日期：2010.3.10

  A total synthesis of the Aspidosperma alkaloids (+)-fendleridine and (+)-1-acetylaspidoalbidine is detailed, providing access to both enantiomers of the natural products and establishing their absolute configuration. Central to the synthetic approach is a powerful intramolecular [4+2]/[3+2] cycloaddition cascade of a 1,3,4-oxadiazole in which the pentacyclic skeleton and all the stereochemistry of

  详细介绍了 Aspidosperma 生物碱 (+)-fendleridine 和 (+)-1-acetylaspidoalbidine 的全合成，提供了对天然产物的两种对映异构体的访问并确定了它们的绝对构型。合成方法的核心是 1,3,4-恶二唑的强大分子内 [4+2]/[3+2] 环加成级联，其中五环骨架和天然产物的所有立体化学组装在一个反应​​中形成三个环、四个 CC 键和五个立体中心，包括三个连续的四元中心，并在单个合成操作中在 C19 处引入正确的氧化态。最终的四氢呋喃桥随后一步安装，通过氮辅助打开环加合物氧化桥产生的亚胺离子加入分子内醇，
• Silver-Catalyzed Radical Phosphonofluorination of Unactivated Alkenes
  作者：Chengwei Zhang、Zhaodong Li、Lin Zhu、Limei Yu、Zhentao Wang、Chaozhong Li

  DOI：10.1021/ja408031s

  日期：2013.9.25

  We report herein a mild and catalytic phosphonofluorination of unactivated alkenes. With catalysis by AgNO3, the condensation of various unactivated alkenes with diethyl phosphite and Selectfluor reagent in CH2Cl2/H2O/HOAc at 40 degrees C led to the efficient synthesis of beta-fluorinated alkylphosphonates with good stereoselectivity and wide functional group compatibility. A mechanism involving silver-catalyzed oxidative generation of phosphonyl radicals and silver-assisted fluorine atom transfer is proposed.
• Total Syntheses of Leuconoxine, Leuconodine B, and Melodinine E by Oxidative Cyclic Aminal Formation and Diastereoselective Ring-Closing Metathesis
  作者：Atsushi Umehara、Hirofumi Ueda、Hidetoshi Tokuyama

  DOI：10.1021/ol500903e

  日期：2014.5.2

  Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.