5,6-Bis-trimethylsilanylethynyl-3,6-dihydro-[1,2]oxazine-2-carboxylic acid 2,2,2-trichloro-ethyl ester | 202215-50-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 5,6-Bis-trimethylsilanylethynyl-3,6-dihydro-[1,2]oxazine-2-carboxylic acid 2,2,2-trichloro-ethyl ester
• 英文别名: 2,2,2-Trichloroethyl 5,6-bis(2-trimethylsilylethynyl)-3,6-dihydrooxazine-2-carboxylate；2,2,2-trichloroethyl 5,6-bis(2-trimethylsilylethynyl)-3,6-dihydrooxazine-2-carboxylate
• CAS: 202215-50-7
• 化学式: C₁₇H₂₄Cl₃NO₃Si₂
• 分子量: 452.912
• InChiKey: RUBSZXISEASVDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-Bis-trimethylsilanylethynyl-3,6-dihydro-[1,2]oxazine-2-carboxylic acid 2,2,2-trichloro-ethyl ester 在 盐酸 、 三乙胺 、 锌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.75h， 生成 2,2,2-trichloroethyl N-[(Z)-4-hydroxy-6-trimethylsilyl-3-(2-trimethylsilylethynyl)hex-2-en-5-ynyl]carbamate
  参考文献：
  名称：

  Toward the Construction of Enediyne Prodrug Systems Related to the Ring Expanded Artifact Produced Upon Isolation of Maduropeptin Chromophore

  摘要：

  As part of a modular approach to synthesize maduropeptin analogues of general formula 3, the diacetylene substituted dihydro-1,2-oxazine synthon 13 was constructed via a hetero Diels-Alder reaction between diene 10 and the nitrosodienophile 12. Reductive cleavage of the N-O bond in 13, and acylation of the derived amine 16 gave the stable amide 17. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10459-2
• 作为产物：
  描述：

  ethyl (Z)-2-bromo-5-trimethylsilylpent-2-en-4-ynoate 在 copper(l) iodide 、 正丁基锂 、 二异丁基氢化铝 、 tetraethylammonium metaperiodate 、 钯 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 17.3h， 生成 5,6-Bis-trimethylsilanylethynyl-3,6-dihydro-[1,2]oxazine-2-carboxylic acid 2,2,2-trichloro-ethyl ester
  参考文献：
  名称：

  Toward the Construction of Enediyne Prodrug Systems Related to the Ring Expanded Artifact Produced Upon Isolation of Maduropeptin Chromophore

  摘要：

  As part of a modular approach to synthesize maduropeptin analogues of general formula 3, the diacetylene substituted dihydro-1,2-oxazine synthon 13 was constructed via a hetero Diels-Alder reaction between diene 10 and the nitrosodienophile 12. Reductive cleavage of the N-O bond in 13, and acylation of the derived amine 16 gave the stable amide 17. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10459-2

文献信息

• Toward the Construction of Enediyne Prodrug Systems Related to the Ring Expanded Artifact Produced Upon Isolation of Maduropeptin Chromophore
  作者：Cécile Roger、David S Grierson

  DOI：10.1016/s0040-4039(97)10459-2

  日期：1998.1

  As part of a modular approach to synthesize maduropeptin analogues of general formula 3, the diacetylene substituted dihydro-1,2-oxazine synthon 13 was constructed via a hetero Diels-Alder reaction between diene 10 and the nitrosodienophile 12. Reductive cleavage of the N-O bond in 13, and acylation of the derived amine 16 gave the stable amide 17. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.