N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide | 350032-43-8

• 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: N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide
• 英文别名: N-[(3aS,4R,5S,7aS)-5-[[(3aS,4R,5S,7aS)-7-bromo-4-hydroxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-yl]amino]-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-yl]-4-methylbenzenesulfonamide
• CAS: 350032-43-8
• 化学式: C₂₅H₃₂Br₂N₂O₇S
• 分子量: 664.412
• InChiKey: FWDSGBXYUSVAME-DNNYETPZSA-N

物化性质

• 沸点：
  727.7±70.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 acetic acid 7-bromo-5S-[[7-bromo-2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl ester
  参考文献：
  名称：

  Paul, Bernhard J.; Martinot, Theodore A.; Willis, Jerremey, Synthesis, 2001, # 6, p. 952 - 956

  摘要：

  DOI：
• 作为产物：
  描述：

  (3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 在 copper acetylacetonate 、 氨 、 ytterbium(III) triflate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 生成 N-[7-bromo-5S-(7-bromo-4S-hydroxy-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino)-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl]-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  Synthesis, Structure, and Biological Evaluation of Novel N- and O-Linked Diinositols

  摘要：

  Several O-and N-linked inositols and/or aminoinositols have been prepared by iterative opening of epoxides and aziridines derived from homochiral cyclohexadiene cis-diols. The three inositols and their intermediate conduritols (conduramines) were tested against several glycosiclases (alpha- and beta-glucosidase, alpha- and beta-galactosidase, alpha- and beta-mannosidase) in an assay that measured the rate of hydrolysis of p-nitrophenolglycosides rather than the concentration of p-nitrophenolate. Somewhat surprisingly, the best inhibition was seen against beta-galactosidase with several of the compounds. The inositols linked through oxygen or nitrogen were subjected to calcium binding studies performed in NMR experiments. Detailed analysis of the title compounds by NMR spectroscopy has been performed, and full assignments were made. One of the attendant benefits of the preparation of these compounds has been expressed in the design and synthesis of new salen catalysts whose effectiveness has been compared with Jacobsen's catalyst in the epoxidation of styrene.

  DOI：

  10.1021/ja0205378

文献信息

• Paul, Bernhard J.; Martinot, Theodore A.; Willis, Jerremey, Synthesis, 2001, # 6, p. 952 - 956
  作者：Paul, Bernhard J.、Martinot, Theodore A.、Willis, Jerremey、Hudlicky, Tomas

  DOI：——

  日期：——
• Synthesis, Structure, and Biological Evaluation of Novel <i>N</i>- and <i>O</i>-Linked Diinositols
  作者：Bernhard J. Paul、Jerremey Willis、Theodore A. Martinot、Ion Ghiviriga、Khalil A. Abboud、Tomas Hudlicky

  DOI：10.1021/ja0205378

  日期：2002.9.1

  Several O-and N-linked inositols and/or aminoinositols have been prepared by iterative opening of epoxides and aziridines derived from homochiral cyclohexadiene cis-diols. The three inositols and their intermediate conduritols (conduramines) were tested against several glycosiclases (alpha- and beta-glucosidase, alpha- and beta-galactosidase, alpha- and beta-mannosidase) in an assay that measured the rate of hydrolysis of p-nitrophenolglycosides rather than the concentration of p-nitrophenolate. Somewhat surprisingly, the best inhibition was seen against beta-galactosidase with several of the compounds. The inositols linked through oxygen or nitrogen were subjected to calcium binding studies performed in NMR experiments. Detailed analysis of the title compounds by NMR spectroscopy has been performed, and full assignments were made. One of the attendant benefits of the preparation of these compounds has been expressed in the design and synthesis of new salen catalysts whose effectiveness has been compared with Jacobsen's catalyst in the epoxidation of styrene.