1,5,9-tris-(2-(trimethylsilyl)ethanesulfonyl)-1,5,9-triazacyclotetradecane [3,3,5] | 652130-82-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1,5,9-tris-(2-(trimethylsilyl)ethanesulfonyl)-1,5,9-triazacyclotetradecane [3,3,5]
• 英文别名: 1,5,9-Triazacyclotetradecane, 1,5,9-tris[[2-(trimethylsilyl)ethyl]sulfonyl]-；2-[[1,9-bis(2-trimethylsilylethylsulfonyl)-1,5,9-triazacyclotetradec-5-yl]sulfonyl]ethyl-trimethylsilane
• CAS: 652130-82-0
• 化学式: C₂₆H₆₁N₃O₆S₃Si₃
• 分子量: 692.241
• InChiKey: JOQBQYNTICOXNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,5,9-tris-(2-(trimethylsilyl)ethanesulfonyl)-1,5,9-triazacyclotetradecane [3,3,5] 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以62%的产率得到1,5,9-triazacyclotetradecane [3,3,5]
  参考文献：
  名称：

  A practical method for building linear and cyclic triamines from (2-trimethylsilyl)ethanesulfonamides (SES-amides)

  摘要：

  SES-chloride has been obtained in higher yield and purity by improving Weinreb's original procedure, allowing efficient access to the primary SES-amide. Linear triamines can be built conveniently from the SES-amide in high yields, with the potential for orthogonal protection. The modified Richman-Atkins cyclisation of SES-amides allows access to novel biologically interesting triazamacrocycles with combinations of three-, four-, five- and six-carbon bridges within the ring. Purification of the free macrocyclic amines by distillation greatly simplifies the workup, increasing the practicability of multi-gram scale synthesis. Although CsF sometimes provided undesirably low yields in the deprotection step, alternative fluoride sources were found to be unsuitable for the deprotection of SES-triazamacrocycles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.067
• 作为产物：
  描述：

  2-(三甲基硅基)乙烷磺酰氯 在 caesium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 生成 1,5,9-tris-(2-(trimethylsilyl)ethanesulfonyl)-1,5,9-triazacyclotetradecane [3,3,5]
  参考文献：
  名称：

  A practical method for building linear and cyclic triamines from (2-trimethylsilyl)ethanesulfonamides (SES-amides)

  摘要：

  SES-chloride has been obtained in higher yield and purity by improving Weinreb's original procedure, allowing efficient access to the primary SES-amide. Linear triamines can be built conveniently from the SES-amide in high yields, with the potential for orthogonal protection. The modified Richman-Atkins cyclisation of SES-amides allows access to novel biologically interesting triazamacrocycles with combinations of three-, four-, five- and six-carbon bridges within the ring. Purification of the free macrocyclic amines by distillation greatly simplifies the workup, increasing the practicability of multi-gram scale synthesis. Although CsF sometimes provided undesirably low yields in the deprotection step, alternative fluoride sources were found to be unsuitable for the deprotection of SES-triazamacrocycles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.067

文献信息

• A practical method for building linear and cyclic triamines from (2-trimethylsilyl)ethanesulfonamides (SES-amides)
  作者：Laurie L Parker、Nicholas D Gowans、Stephen W Jones、David J Robins

  DOI：10.1016/j.tet.2003.10.067

  日期：2003.12

  SES-chloride has been obtained in higher yield and purity by improving Weinreb's original procedure, allowing efficient access to the primary SES-amide. Linear triamines can be built conveniently from the SES-amide in high yields, with the potential for orthogonal protection. The modified Richman-Atkins cyclisation of SES-amides allows access to novel biologically interesting triazamacrocycles with combinations of three-, four-, five- and six-carbon bridges within the ring. Purification of the free macrocyclic amines by distillation greatly simplifies the workup, increasing the practicability of multi-gram scale synthesis. Although CsF sometimes provided undesirably low yields in the deprotection step, alternative fluoride sources were found to be unsuitable for the deprotection of SES-triazamacrocycles. (C) 2003 Elsevier Ltd. All rights reserved.