diisopropyl {[trans-2-(7-methoxy-1,3-benzodioxol-5-yl)ethenylsulfonyl]methylsulfonylmethyl}phosphonate | 1154763-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: diisopropyl {[trans-2-(7-methoxy-1,3-benzodioxol-5-yl)ethenylsulfonyl]methylsulfonylmethyl}phosphonate
• 英文别名: 6-[(E)-2-[di(propan-2-yloxy)phosphorylmethylsulfonylmethylsulfonyl]ethenyl]-4-methoxy-1,3-benzodioxole
• CAS: 1154763-33-3
• 化学式: C₁₈H₂₇O₁₀PS₂
• 分子量: 498.512
• InChiKey: BEDJERZMCFXHQY-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  肉豆蔻醛 、 (diisopropoxyphosphorylmethanesulfonylmethanesulfonylmethyl)phosphonic acid diisopropyl ester 在 N,N-二异丙基乙胺 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 生成 diisopropyl {[trans-2-(7-methoxy-1,3-benzodioxol-5-yl)ethenylsulfonyl]methylsulfonylmethyl}phosphonate
  参考文献：
  名称：

  Vinyl sulfones

  摘要：

  Four neutral vinyl sulfones, two of which are paired with phosphonate groups, are described. The compounds are diisopropyl (2-phenylethenylsulfonylmethyl) phosphonate, C15H23O5PS, (I), diisopropyl {[2-(7-methoxy-1,3-benzodioxol-5-yl) ethenylsulfonyl]methylsulfonylmethyl} phosphonate, C18H27O10PS2, (II), bis(trans-2-phenylethenyl) sulfone, C16H14O2S, (III), and bis(trans-2-phenylethenylsulfonyl) methane, C17H16O4S2, (IV). Their structures can be considered as highly functionalized mimics of mono-, di- and triphosphates. These phosphate isosteres are currently of interest as agents for enzyme inhibition in both cancer and HIV therapy. All except one of the compounds has Z' > 1. The lone exception is (IV), a disulfone with twofold crystallographic symmetry. Geometrically, the sulfone functionality is found to be a good mimic for phosphate. The principal effect of the vinyl group is to shorten the S-C(vinyl) distance relative to the S-CH2 distance by ca 0.05 angstrom. The S-C-S and S-C-P backbones resemble the P-O-P backbone but are not identical because the S - C and P - C distances are longer than the P-O distance and the S-C-S and S-C-P angles are more acute than the P-O-P angle. No prior crystal structures of comparable compounds have been published.

  DOI：

  10.1107/s0108270108002692

文献信息

• Vinyl sulfones
  作者：Jessica H. Wong、Marilyn M. Olmstead、James C. Fettinger、Jacquelyn Gervay-Hague

  DOI：10.1107/s0108270108002692

  日期：2008.3.15

  Four neutral vinyl sulfones, two of which are paired with phosphonate groups, are described. The compounds are diisopropyl (2-phenylethenylsulfonylmethyl) phosphonate, C15H23O5PS, (I), diisopropyl [2-(7-methoxy-1,3-benzodioxol-5-yl) ethenylsulfonyl]methylsulfonylmethyl} phosphonate, C18H27O10PS2, (II), bis(trans-2-phenylethenyl) sulfone, C16H14O2S, (III), and bis(trans-2-phenylethenylsulfonyl) methane, C17H16O4S2, (IV). Their structures can be considered as highly functionalized mimics of mono-, di- and triphosphates. These phosphate isosteres are currently of interest as agents for enzyme inhibition in both cancer and HIV therapy. All except one of the compounds has Z' > 1. The lone exception is (IV), a disulfone with twofold crystallographic symmetry. Geometrically, the sulfone functionality is found to be a good mimic for phosphate. The principal effect of the vinyl group is to shorten the S-C(vinyl) distance relative to the S-CH2 distance by ca 0.05 angstrom. The S-C-S and S-C-P backbones resemble the P-O-P backbone but are not identical because the S - C and P - C distances are longer than the P-O distance and the S-C-S and S-C-P angles are more acute than the P-O-P angle. No prior crystal structures of comparable compounds have been published.