trans-3,4-di-(diethoxyphosphoryl)chroman-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: trans-3,4-di-(diethoxyphosphoryl)chroman-2-one
• 英文别名: (3S,4S)-3,4-bis(diethoxyphosphoryl)-3,4-dihydrochromen-2-one
• 化学式: C₁₇H₂₆O₈P₂
• 分子量: 420.336
• InChiKey: ZWKVOIRCYZYVON-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 trans-3,4-di-(diethoxyphosphoryl)chroman-2-one 在 sodium hydride 作用下， 以 苯 为溶剂， 反应 1.0h， 以63%的产率得到4-diethoxyphosphoryl-3-methylchromen-2-one
  参考文献：
  名称：

  A novel route to substituted 3-methylidenechroman-2-ones and 3-methylchromen-2-ones

  摘要：

  3-Methylidenechroman-2-ones, or their rearrangement products 3-methylchromen-2-ones, were efficiently synthesized by Michael addition of various nucleophiles to 3-diethoxyphosphorylchromen-2-ones followed by Horner-Wadsworth-Emmons reaction of the adducts with formaldehyde. Relative configuration and conformation of the intermediate adducts were studied using NMR spectroscopy and semiempirical PM3 calculations. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.083
• 作为产物：
  描述：

  sodium diethyl phosphite 、 diethyl (2-oxo-2H-chromen-3-yl)phosphonate 以 四氢呋喃 为溶剂， 反应 3.0h， 以73%的产率得到trans-3,4-di-(diethoxyphosphoryl)chroman-2-one
  参考文献：
  名称：

  A novel route to substituted 3-methylidenechroman-2-ones and 3-methylchromen-2-ones

  摘要：

  3-Methylidenechroman-2-ones, or their rearrangement products 3-methylchromen-2-ones, were efficiently synthesized by Michael addition of various nucleophiles to 3-diethoxyphosphorylchromen-2-ones followed by Horner-Wadsworth-Emmons reaction of the adducts with formaldehyde. Relative configuration and conformation of the intermediate adducts were studied using NMR spectroscopy and semiempirical PM3 calculations. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.083

文献信息

• A novel route to substituted 3-methylidenechroman-2-ones and 3-methylchromen-2-ones
  作者：Tomasz Janecki、Tomasz Wąsek

  DOI：10.1016/j.tet.2003.11.083

  日期：2004.1

  3-Methylidenechroman-2-ones, or their rearrangement products 3-methylchromen-2-ones, were efficiently synthesized by Michael addition of various nucleophiles to 3-diethoxyphosphorylchromen-2-ones followed by Horner-Wadsworth-Emmons reaction of the adducts with formaldehyde. Relative configuration and conformation of the intermediate adducts were studied using NMR spectroscopy and semiempirical PM3 calculations. (C) 2003 Elsevier Ltd. All rights reserved.