3'-[diethoxy(oxido)phosphaniumyl]-4'a-methylspiro[1,3-dioxolane-2,5'-4,6,7,8-tetrahydro-3H-naphthalene]-2'-one | 137626-88-1

• 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: 3'-[diethoxy(oxido)phosphaniumyl]-4'a-methylspiro[1,3-dioxolane-2,5'-4,6,7,8-tetrahydro-3H-naphthalene]-2'-one
• CAS: 137626-88-1；137626-94-9
• 化学式: C₁₇H₂₇O₆P
• 分子量: 358.372
• InChiKey: OXMRIRODEXYXMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-[diethoxy(oxido)phosphaniumyl]-4'a-methylspiro[1,3-dioxolane-2,5'-4,6,7,8-tetrahydro-3H-naphthalene]-2'-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以100%的产率得到rac-diethyl ((4aR,8aR)-8a-methyl-6-oxooctahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolan]-7-yl)phosphonate
  参考文献：
  名称：

  Regiochemistry of vinyl phosphate/.beta.-keto phosphonate rearrangements in functionalized cyclohexanones and decalones

  摘要：

  Diethyl vinyl phosphates derived from simple alkyl-substituted cyclohexanones and cyclohexenones are known to rearrange to beta-keto phosphonates upon treatment with excess LDA. To establish the effect of oxygen-containing functional groups on this transformation, vinyl phosphates containing remote carbonyl groups or acetals have been studied. The rearrangement fails in the presence of unprotected carbonyl groups but proceeds in the presence of acetals. To establish the regiochemistry of this rearrangement in fused-ring systems, representative decalins were studied. Through use of various ketones and enones, the 2- and 4-phosphono 3-keto compounds have been prepared in both cis-and trans-fused decalin series.

  DOI：

  10.1021/jo00027a055
• 作为产物：
  描述：

  diethyl (8a-methyl-3,4,8,8a-tetrahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolan]-6-yl) phosphate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到3'-[diethoxy(oxido)phosphaniumyl]-4'a-methylspiro[1,3-dioxolane-2,5'-4,6,7,8-tetrahydro-3H-naphthalene]-2'-one
  参考文献：
  名称：

  Regiochemistry of vinyl phosphate/.beta.-keto phosphonate rearrangements in functionalized cyclohexanones and decalones

  摘要：

  Diethyl vinyl phosphates derived from simple alkyl-substituted cyclohexanones and cyclohexenones are known to rearrange to beta-keto phosphonates upon treatment with excess LDA. To establish the effect of oxygen-containing functional groups on this transformation, vinyl phosphates containing remote carbonyl groups or acetals have been studied. The rearrangement fails in the presence of unprotected carbonyl groups but proceeds in the presence of acetals. To establish the regiochemistry of this rearrangement in fused-ring systems, representative decalins were studied. Through use of various ketones and enones, the 2- and 4-phosphono 3-keto compounds have been prepared in both cis-and trans-fused decalin series.

  DOI：

  10.1021/jo00027a055

文献信息

• Regiochemistry of vinyl phosphate/.beta.-keto phosphonate rearrangements in functionalized cyclohexanones and decalones
  作者：Yi Zhong An、David F. Wiemer

  DOI：10.1021/jo00027a055

  日期：1992.1

  Diethyl vinyl phosphates derived from simple alkyl-substituted cyclohexanones and cyclohexenones are known to rearrange to beta-keto phosphonates upon treatment with excess LDA. To establish the effect of oxygen-containing functional groups on this transformation, vinyl phosphates containing remote carbonyl groups or acetals have been studied. The rearrangement fails in the presence of unprotected carbonyl groups but proceeds in the presence of acetals. To establish the regiochemistry of this rearrangement in fused-ring systems, representative decalins were studied. Through use of various ketones and enones, the 2- and 4-phosphono 3-keto compounds have been prepared in both cis-and trans-fused decalin series.