tert-butyl-[(1R,2R)-4-[diethoxy(oxido)phosphaniumyl]-2-methylcyclohept-3-en-1-yl]oxy-dimethylsilane | 1108178-00-2

• 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: tert-butyl-[(1R,2R)-4-[diethoxy(oxido)phosphaniumyl]-2-methylcyclohept-3-en-1-yl]oxy-dimethylsilane
• CAS: 1108178-00-2
• 化学式: C₁₈H₃₇O₄PSi
• 分子量: 376.549
• InChiKey: FOXBQAOCUBEZRF-NVXWUHKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 tert-butyl-[(1R,2R)-4-[diethoxy(oxido)phosphaniumyl]-2-methylcyclohept-3-en-1-yl]oxy-dimethylsilane 在 吡啶 、 臭氧 、 4-二甲氨基吡啶 、 三溴化硼 、 叔丁胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以82%的产率得到methyl (5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-6-methylheptanoate
  参考文献：
  名称：

  Designer Discodermolide Segments via Ozonolysis of Vinyl Phosphonates

  摘要：

  To apply our collection of enantiopure 7-ring vinyl sulfones to probe the anticancer SAR of a series of computer-designed (+)-discodermolide analogs, the ozonolytic reactivity of transposed cyclic vinyl phosphonates was explored. Successful preparation of the desired aldehyde-esters and lactones from vinyl phosphonates via an oxidative cleavage-phosphite/methanol exchange sequence is described.

  DOI：

  10.1021/ol802503h
• 作为产物：
  描述：

  、 亚磷酸二乙酯 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到tert-butyl-[(1R,2R)-4-[diethoxy(oxido)phosphaniumyl]-2-methylcyclohept-3-en-1-yl]oxy-dimethylsilane
  参考文献：
  名称：

  Conversion of Cyclic Vinyl Sulfones to Transposed Vinyl Phosphonates

  摘要：

  Functionalized cyclic vinyl sulfones were directly converted to the "polarity reversed" vinyl phosphonates through an efficient one pot procedure. Ozonolysis of these vinyl sulfones and vinyl phosphonates furnish complementary sets of termini-differentiated ester-aldehydes. This strategy has been applied for preparation of segments needed for the synthesis of Aplyronine A. The scope and limitations of this transformation were defined.

  DOI：

  10.1021/ja072890p

文献信息

• Designer Discodermolide Segments via Ozonolysis of Vinyl Phosphonates
  作者：Xavier Mollat du Jourdin、Mohammad Noshi、P. L. Fuchs

  DOI：10.1021/ol802503h

  日期：2009.2.5

  To apply our collection of enantiopure 7-ring vinyl sulfones to probe the anticancer SAR of a series of computer-designed (+)-discodermolide analogs, the ozonolytic reactivity of transposed cyclic vinyl phosphonates was explored. Successful preparation of the desired aldehyde-esters and lactones from vinyl phosphonates via an oxidative cleavage-phosphite/methanol exchange sequence is described.
• Conversion of Cyclic Vinyl Sulfones to Transposed Vinyl Phosphonates
  作者：Mohammad N. Noshi、Ahmad El-awa、Eduardo Torres、Philip L. Fuchs

  DOI：10.1021/ja072890p

  日期：2007.9.1

  Functionalized cyclic vinyl sulfones were directly converted to the "polarity reversed" vinyl phosphonates through an efficient one pot procedure. Ozonolysis of these vinyl sulfones and vinyl phosphonates furnish complementary sets of termini-differentiated ester-aldehydes. This strategy has been applied for preparation of segments needed for the synthesis of Aplyronine A. The scope and limitations of this transformation were defined.