(+)-N-{(3R,4R)-4-(1-bromovinyl)-1-tosylpyrrolidin-3-yl}-acetamide | 1541176-87-7

• 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-{(3R,4R)-4-(1-bromovinyl)-1-tosylpyrrolidin-3-yl}-acetamide
• CAS: 1541176-87-7
• 化学式: C₁₅H₁₉BrN₂O₃S
• 分子量: 387.297
• InChiKey: PFFLQCBIIIFFAD-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+)-N-{(3R,4R)-4-(1-bromovinyl)-1-tosylpyrrolidin-3-yl}-acetamide 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以67%的产率得到(-)-N-{(3R,4R)-4-(4-phenylbut-1-en-3-yn-2-yl)-1-tosylpyrrolidin-3-yl}acetamide
  参考文献：
  名称：

  Regulation of Diastereoselectivity in the Carbocyclization of Allenyl (S)-N-tert-Butylsulfinimines through a Three-Component Assembly

  摘要：

  Allenyl sulfinimines can be stereoselectively cyclized with hexamethylditin under palladium catalysis conditions followed by a selection of additives for an activated transmetalation. Reactivity and diastereoselectivity for the cyclization strongly depend on the characteristics of additives. A highly diastereoselective synthesis of five-membered rings is achieved from the reaction of the corresponding allenyl (5)-N-tert-butylsulfinimies through the following sequence. After the distannylation of the allenyl group with hexamethylditin catalyzed by the Pd complex, stereochemical routes are additive dependent: addition of SnCl4 affords a cis ring exclusively, whereas a trans ring is formed predominantly by the introduction of B-bromocatecholborane. Extension of the methodology to the synthesis of six-membered cis rings is achieved by using B-bromocatecholborane. Stereochemical relationships of products were unambiguously deduced by X-ray crystallography.

  DOI：

  10.1021/jo4025072
• 作为产物：
  描述：

  (+)-(S)-2-methyl-N-[(3R,4R)-1-tosyl-4-{1-(trimethylstannyl)vinyl}pyrrolidin-3-yl]propane-2-sulfinamide 在 溴 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (+)-N-{(3R,4R)-4-(1-bromovinyl)-1-tosylpyrrolidin-3-yl}-acetamide
  参考文献：
  名称：

  Regulation of Diastereoselectivity in the Carbocyclization of Allenyl (S)-N-tert-Butylsulfinimines through a Three-Component Assembly

  摘要：

  Allenyl sulfinimines can be stereoselectively cyclized with hexamethylditin under palladium catalysis conditions followed by a selection of additives for an activated transmetalation. Reactivity and diastereoselectivity for the cyclization strongly depend on the characteristics of additives. A highly diastereoselective synthesis of five-membered rings is achieved from the reaction of the corresponding allenyl (5)-N-tert-butylsulfinimies through the following sequence. After the distannylation of the allenyl group with hexamethylditin catalyzed by the Pd complex, stereochemical routes are additive dependent: addition of SnCl4 affords a cis ring exclusively, whereas a trans ring is formed predominantly by the introduction of B-bromocatecholborane. Extension of the methodology to the synthesis of six-membered cis rings is achieved by using B-bromocatecholborane. Stereochemical relationships of products were unambiguously deduced by X-ray crystallography.

  DOI：

  10.1021/jo4025072