3,7-bis(4-methylbenzenesulfonyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-1,5-diol | 202211-14-1

• 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: 3,7-bis(4-methylbenzenesulfonyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-1,5-diol
• 英文别名: 3,7-Bis-(4-methylphenyl)sulfonyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane-1,5-diol
• CAS: 202211-14-1
• 化学式: C₂₀H₂₄N₂O₇S₂
• 分子量: 468.552
• InChiKey: CQFJOMPBGWRESO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,7-bis(4-methylbenzenesulfonyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-1,5-diol 生成 1,5-ditosyl-1,5-diazocane-3,7-dione
  参考文献：
  名称：

  Difluoramination of Heterocyclic Ketones:  Control of Microbasicity

  摘要：

  Difluoramination of a tetrahydro-1,5-diazocine-3,7(2H, 6H)-dione to the corresponding 3,3,7,7-tetrakis(difluoramino)diazocine was achieved by a judicious choice of protecting group. Arenesulfonyl protecting groups for the diazocine nitrogens proved superior to acetyl during the slow disruption of the transannular bridge in 9-oxa-3,7-diazabicyclo[3.3.1]nonane intermediates by difluorosulfamic acid, While a 1,5-ditosyl derivative failed to proceed beyond the product of addition of difluoramine to one ketone carbonyl (hemiaminal 6), the use of 4-nitrobenzenesulfonyl as the protecting groups lowered the nitrogens' basicities below that of the oxygen site in the dione and intermediates, allowing the reaction to proceed to a gem-bis(difluoramino)diazocine product (11). A safer procedure for handling difluoramine is described.

  DOI：

  10.1021/jo9718399
• 作为产物：
  描述：

  1,5-bis-(toluene-4-sulfonyl)-[1,5]diazocane-3,7-diol 生成 3,7-bis(4-methylbenzenesulfonyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-1,5-diol
  参考文献：
  名称：

  Difluoramination of Heterocyclic Ketones:  Control of Microbasicity

  摘要：

  Difluoramination of a tetrahydro-1,5-diazocine-3,7(2H, 6H)-dione to the corresponding 3,3,7,7-tetrakis(difluoramino)diazocine was achieved by a judicious choice of protecting group. Arenesulfonyl protecting groups for the diazocine nitrogens proved superior to acetyl during the slow disruption of the transannular bridge in 9-oxa-3,7-diazabicyclo[3.3.1]nonane intermediates by difluorosulfamic acid, While a 1,5-ditosyl derivative failed to proceed beyond the product of addition of difluoramine to one ketone carbonyl (hemiaminal 6), the use of 4-nitrobenzenesulfonyl as the protecting groups lowered the nitrogens' basicities below that of the oxygen site in the dione and intermediates, allowing the reaction to proceed to a gem-bis(difluoramino)diazocine product (11). A safer procedure for handling difluoramine is described.

  DOI：

  10.1021/jo9718399

文献信息

• Nitrolysis of a Highly Deactivated Amide by Protonitronium. Synthesis and Structure of HNFX¹
  作者：Robert D. Chapman、Richard D. Gilardi、Mark F. Welker、Charles B. Kreutzberger

  DOI：10.1021/jo9819640

  日期：1999.2.1

  Efficient N-nitrolysis of highly deactivated 3,3,7,7-tetrakis(difluoramino)octahydro-1,5-bis(4-ni- trobenzenesulfonyl)-1,5-diazocine (1) has been achieved by the use of protonitronium reagent formed in the system nitric acid-trifluoromethanesulfonic acid, producing 3,3,7,7-tetrakis(difluoramino)octahydro-1,5-dinitro-1,5-diazocine (HNFX, 2) in 65% yield in a nonoptimized reaction. The crystal structure of the first morphology of HNFX contains cavities in the form of channels through its unit cell; the observed density is 1.807 g . cm(-3).
• Difluoramination of Heterocyclic Ketones:  Control of Microbasicity
  作者：Robert D. Chapman、Mark F. Welker、Charles B. Kreutzberger

  DOI：10.1021/jo9718399

  日期：1998.3.1

  Difluoramination of a tetrahydro-1,5-diazocine-3,7(2H, 6H)-dione to the corresponding 3,3,7,7-tetrakis(difluoramino)diazocine was achieved by a judicious choice of protecting group. Arenesulfonyl protecting groups for the diazocine nitrogens proved superior to acetyl during the slow disruption of the transannular bridge in 9-oxa-3,7-diazabicyclo[3.3.1]nonane intermediates by difluorosulfamic acid, While a 1,5-ditosyl derivative failed to proceed beyond the product of addition of difluoramine to one ketone carbonyl (hemiaminal 6), the use of 4-nitrobenzenesulfonyl as the protecting groups lowered the nitrogens' basicities below that of the oxygen site in the dione and intermediates, allowing the reaction to proceed to a gem-bis(difluoramino)diazocine product (11). A safer procedure for handling difluoramine is described.