dimethyl [6-(methoxycarbonyl)-2-oxohexyl]phosphonate | 58648-51-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dimethyl [6-(methoxycarbonyl)-2-oxohexyl]phosphonate
• 英文别名: Dimethyl <6-(methoxycarbonyl)-2-oxohexyl>phosphonate；Dimethyl-2-keto-6-carbomethoxy-n-hexylphosphonat；Heptanoic acid, 7-(dimethoxyphosphinyl)-6-oxo-, methyl ester；methyl 7-dimethoxyphosphoryl-6-oxoheptanoate
• CAS: 58648-51-4
• 化学式: C₁₀H₁₉O₆P
• 分子量: 266.231
• InChiKey: MGXGVPPJHSJKLE-UHFFFAOYSA-N

物化性质

• 沸点：
  365.5±27.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl [6-(methoxycarbonyl)-2-oxohexyl]phosphonate 、 (1R,2R,3S,4S)-1,4-di(benzoyloxy)-2-formyl-3-(2-methoxycarbonylethyl)cyclopentane 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以258 mg的产率得到(1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxohept-1-enyl)cyclopentane
  参考文献：
  名称：

  自由基环化；对15-F 2t-异前列腺素的四甲酸酯代谢产物的合成

  摘要：

  无环的1-取代的2，4-二羟基化的5-己烯基的自由基环化产生官能化的环戊烷衍生物。不同的保护/脱保护反应后，这些前体cyclopentanic随后的Wittig和霍纳-沃兹沃思-埃蒙斯耦合导致15-F的主要尿代谢物四去甲反应2吨-isoprostane（8-外延-PGF 2α）。

  DOI：

  10.1016/s0040-4020(03)00258-8
• 作为产物：
  描述：

  脂肪酸甲酯 在 4-二甲氨基吡啶 、 正丁基锂 、 4-(dimethylamino)pyridine hydrochloride 、 草酸 、 N,N'-二环己基碳二亚胺 作用下， 反应 10.08h， 生成 dimethyl [6-(methoxycarbonyl)-2-oxohexyl]phosphonate
  参考文献：
  名称：

  New Syntheses of Some Functionalized and Acetylenic .beta.-Keto Phosphonates

  摘要：

  beta-Keto phosphonates omega-functionalized by an ester group 1a-f, by a hydroxyl 5, and with a triple bond conjugated to the carbonyl group 2a-c were prepared by reacting dimethyl (lithiomethyl)phosphonate (3) with adequate electrophiles. Cyclic anhydrides such as succinic, and- glutaric anhydrides were employed for the synthesis of the two first homologs 1a and 1b. To obtain the other longer homologs 1c-f, 3-acylthiazolidine-2-thiones 7a-d easily prepared using cheap 2-mercaptothiazoline proved to be the electrophiles of choice. On the other hand, the synthesis of keto phosphonates 2a-c required the use of N-methoxy-N-methylamides.

  DOI：

  10.1021/jo00097a058

文献信息

• Stereoselective total synthesis of 7α-hydroxy-5,11-diketotetranor-prostane-1,16-dioic acid, the major human urinary metabolite of PGE1 and PGE2
  作者：D. Taub、Z.S. Zelawski、N.L. Wendler

  DOI：10.1016/s0040-4039(00)91303-0

  日期：1975.1
• Delamarche Isabelle, Mosset Paul, J. Org. Chem, 59 (1994) N 18, S 5453-5457
  作者：Delamarche Isabelle, Mosset Paul

  DOI：——

  日期：——
• New Syntheses of Some Functionalized and Acetylenic .beta.-Keto Phosphonates
  作者：Isabelle Delamarche、Paul Mosset

  DOI：10.1021/jo00097a058

  日期：1994.9

  beta-Keto phosphonates omega-functionalized by an ester group 1a-f, by a hydroxyl 5, and with a triple bond conjugated to the carbonyl group 2a-c were prepared by reacting dimethyl (lithiomethyl)phosphonate (3) with adequate electrophiles. Cyclic anhydrides such as succinic, and- glutaric anhydrides were employed for the synthesis of the two first homologs 1a and 1b. To obtain the other longer homologs 1c-f, 3-acylthiazolidine-2-thiones 7a-d easily prepared using cheap 2-mercaptothiazoline proved to be the electrophiles of choice. On the other hand, the synthesis of keto phosphonates 2a-c required the use of N-methoxy-N-methylamides.
• Radical cyclization; towards the syntheses of tetranor metabolites of 15-F2t-isoprostane
  作者：Thierry Durand、Olivier Henry、Alexandre Guy、Arlène Roland、Jean-Pierre Vidal、Jean-Claude Rossi

  DOI：10.1016/s0040-4020(03)00258-8

  日期：2003.3

  Radical cyclization of acyclic 1-substituted-2,4-dihydroxylated 5-hexenyl radicals produced functionalized cyclopentane derivatives. These cyclopentanic precursors after different protection/deprotection reactions followed by Wittig and Horner–Wadsworth–Emmons coupling reactions led to the main urinary tetranor metabolites of 15-F2t-isoprostane (8-epi-PGF2α).

  无环的1-取代的2，4-二羟基化的5-己烯基的自由基环化产生官能化的环戊烷衍生物。不同的保护/脱保护反应后，这些前体cyclopentanic随后的Wittig和霍纳-沃兹沃思-埃蒙斯耦合导致15-F的主要尿代谢物四去甲反应2吨-isoprostane（8-外延-PGF 2α）。