[3-[3-(2,2-dimethylpropanoyloxy)-2-diphenylphosphoryl-6-methoxyphenyl]-2-diphenylphosphoryl-4-methoxyphenyl] 2,2-dimethylpropanoate | 893447-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [3-[3-(2,2-dimethylpropanoyloxy)-2-diphenylphosphoryl-6-methoxyphenyl]-2-diphenylphosphoryl-4-methoxyphenyl] 2,2-dimethylpropanoate
• CAS: 893447-87-5；894100-00-6；894100-04-0
• 化学式: C₄₈H₄₈O₈P₂
• 分子量: 814.852
• InChiKey: OQSQVDMZVSDJHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  58
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [3-[3-(2,2-dimethylpropanoyloxy)-2-diphenylphosphoryl-6-methoxyphenyl]-2-diphenylphosphoryl-4-methoxyphenyl] 2,2-dimethylpropanoate 在 aluminium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 [6-[dimethyl-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxysilyl]oxy-2-[3-[dimethyl-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxysilyl]oxy-2-diphenylphosphanyl-6-methoxyphenyl]-3-methoxyphenyl]-diphenylphosphane
  参考文献：
  名称：

  Synthesis, resolution and applications of 3,3′-bis(RO)-MeO-BIPHEP derivatives

  摘要：

  A series of optically pure 3,3'-bis(RO)-MeO-BIPHEP derivatives are prepared and used in palladium catalyzed asymmetric transformations. The phosphine oxide of (+/-)-5 is prepared in four steps from p-methoxyphenol and resolved using the novel resolving reagent chloro((L)-menthoxy)dimethylsilane. Subsequent conversions provide catalysts 8 and 9. Ligands 6, 7 and 10 are prepared in six steps from p-methoxyphenol and the phosphine oxides of 6 and 7, and 10 are resolved using di-p-toluoyl- and dibenzoyl-(L)-tartaric acid, respectively. (R)-3,3'-Bispivalate 8 is superior to the other catalysts in asymmetric Heck reaction with 2,3-dihydrofuran while (R)-(+)-bis(tolyloxy) 10 and (+)-(R)-sugar derivative 9 are better in the Pd-catalyzed polyene cyclization; however, the absolute sense of chirality in the product from the polyene cyclization was reversed to that obtained when (R)-(+)BINAP and (R)-(+)-MeO-BIPHEP were used. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.073
• 作为产物：
  描述：

  4-methoxyphenyl diphenylphosphinate 在 铜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 [3-[3-(2,2-dimethylpropanoyloxy)-2-diphenylphosphoryl-6-methoxyphenyl]-2-diphenylphosphoryl-4-methoxyphenyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Synthesis, resolution and applications of 3,3′-bis(RO)-MeO-BIPHEP derivatives

  摘要：

  A series of optically pure 3,3'-bis(RO)-MeO-BIPHEP derivatives are prepared and used in palladium catalyzed asymmetric transformations. The phosphine oxide of (+/-)-5 is prepared in four steps from p-methoxyphenol and resolved using the novel resolving reagent chloro((L)-menthoxy)dimethylsilane. Subsequent conversions provide catalysts 8 and 9. Ligands 6, 7 and 10 are prepared in six steps from p-methoxyphenol and the phosphine oxides of 6 and 7, and 10 are resolved using di-p-toluoyl- and dibenzoyl-(L)-tartaric acid, respectively. (R)-3,3'-Bispivalate 8 is superior to the other catalysts in asymmetric Heck reaction with 2,3-dihydrofuran while (R)-(+)-bis(tolyloxy) 10 and (+)-(R)-sugar derivative 9 are better in the Pd-catalyzed polyene cyclization; however, the absolute sense of chirality in the product from the polyene cyclization was reversed to that obtained when (R)-(+)BINAP and (R)-(+)-MeO-BIPHEP were used. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.073

文献信息

• Use of ¹H NMR chemical shifts to determine the absolute configuration and enantiomeric purity for enantiomers of 3,3′-disubstituted-MeO-BIPHEP derivatives
  作者：Evgueni Gorobets、Masood Parvez、Bronwen MM Wheatley、Brian A Keay

  DOI：10.1139/v05-230

  日期：2006.2.1

  The absolute configuration of a series of 3,3′-disubstituted-MeO-BIPHEP derivatives can be determined by the 1H NMR chemical shift of the methoxyl group when the 3,3′-disubsituted-MeO-BIPHEP deriva...

  一系列3,3'-二取代-MeO-BIPHEP衍生物的绝对构型可以通过3,3'-二取代-MeO-BIPHEP衍生物时甲氧基的1H NMR化学位移确定。
• Synthesis, resolution and applications of 3,3′-bis(RO)-MeO-BIPHEP derivatives
  作者：Evgueni Gorobets、Guang-Ri Sun、Bronwen M.M. Wheatley、Masood Parvez、Brian A. Keay

  DOI：10.1016/j.tetlet.2004.03.073

  日期：2004.4

  A series of optically pure 3,3'-bis(RO)-MeO-BIPHEP derivatives are prepared and used in palladium catalyzed asymmetric transformations. The phosphine oxide of (+/-)-5 is prepared in four steps from p-methoxyphenol and resolved using the novel resolving reagent chloro((L)-menthoxy)dimethylsilane. Subsequent conversions provide catalysts 8 and 9. Ligands 6, 7 and 10 are prepared in six steps from p-methoxyphenol and the phosphine oxides of 6 and 7, and 10 are resolved using di-p-toluoyl- and dibenzoyl-(L)-tartaric acid, respectively. (R)-3,3'-Bispivalate 8 is superior to the other catalysts in asymmetric Heck reaction with 2,3-dihydrofuran while (R)-(+)-bis(tolyloxy) 10 and (+)-(R)-sugar derivative 9 are better in the Pd-catalyzed polyene cyclization; however, the absolute sense of chirality in the product from the polyene cyclization was reversed to that obtained when (R)-(+)BINAP and (R)-(+)-MeO-BIPHEP were used. (C) 2004 Elsevier Ltd. All rights reserved.