(4R,R_S)-N-(tert-butylsulfinyl)-7-bromohept-1-en-4-amine | 1597449-87-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: (4R,R_S)-N-(tert-butylsulfinyl)-7-bromohept-1-en-4-amine
• 英文别名: (R)-N-[(4R)-7-bromohept-1-en-4-yl]-2-methylpropane-2-sulfinamide
• CAS: 1597449-87-0
• 化学式: C₁₁H₂₂BrNOS
• 分子量: 296.272
• InChiKey: NEDZCMZFPMGCMU-ZUZCIYMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  48.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,R_S)-N-(tert-butylsulfinyl)-7-bromohept-1-en-4-amine 在 2,6-二甲基吡啶 、 盐酸 、 titanium(IV) tetraethanolate 、 indium 、 sodium periodate 、 四氧化锇 、 palladium 10% on activated carbon 、 氢气 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 叔丁醇 为溶剂， 60.0 ℃ 、405.33 kPa 条件下， 反应 27.08h， 生成
  参考文献：
  名称：

  Natural Tetraponerines: A General Synthesis and Antiproliferative Activity

  摘要：

  A stereocontrolled general methodology to access all natural tetraponerines from (+)-T1 to (+)-T8 is detailed. Two consecutive indium-mediated aminoallylations with the appropriate enantiomer of chiral N-tert-butylsulfinamide and a thermodynamic control at the aminal stereocenter allow the formation of each natural tetraponerine with excellent stereoselectivity. The use of 4-bromobutanal in the first aminoallylation leads to the formation of 5-6-5 tetraponerines, while 5-bromopentanal is required to build the scaffold of 6-6-5 tetraponerines. A cross-metathesis reaction of the second aminoallylation product with cis-3-hexene is used to elongate the side chain up to 5 carbons so as to prepare the tetraponerines T5 to T8. The anticancer activity of these heavier tetraponerines against four different carcinoma human cell lines is examined, observing a promising cytotcodc activity of (+)-T7 against breast carcinoma cell line MCF-7.

  DOI：

  10.1021/jo500446f
• 作为产物：
  描述：

  4-溴丁醛 、 3-溴丙烯 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 、 indium 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以89%的产率得到(4R,R_S)-N-(tert-butylsulfinyl)-7-bromohept-1-en-4-amine
  参考文献：
  名称：

  Natural Tetraponerines: A General Synthesis and Antiproliferative Activity

  摘要：

  A stereocontrolled general methodology to access all natural tetraponerines from (+)-T1 to (+)-T8 is detailed. Two consecutive indium-mediated aminoallylations with the appropriate enantiomer of chiral N-tert-butylsulfinamide and a thermodynamic control at the aminal stereocenter allow the formation of each natural tetraponerine with excellent stereoselectivity. The use of 4-bromobutanal in the first aminoallylation leads to the formation of 5-6-5 tetraponerines, while 5-bromopentanal is required to build the scaffold of 6-6-5 tetraponerines. A cross-metathesis reaction of the second aminoallylation product with cis-3-hexene is used to elongate the side chain up to 5 carbons so as to prepare the tetraponerines T5 to T8. The anticancer activity of these heavier tetraponerines against four different carcinoma human cell lines is examined, observing a promising cytotcodc activity of (+)-T7 against breast carcinoma cell line MCF-7.

  DOI：

  10.1021/jo500446f