(6S,E)-N-[(S_s)-tert-butanesulfinyl]-6-aminopentadec-3-en-2-one | 1112145-19-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6S,E)-N-[(S_s)-tert-butanesulfinyl]-6-aminopentadec-3-en-2-one
• 英文别名: (1S,S(S))-N-(tert-butylsulfinyl)-((E)-2-oxopentadec-3-en)-6-amine；(S)-2-methyl-N-[(E,6S)-2-oxopentadec-3-en-6-yl]propane-2-sulfinamide
• CAS: 1112145-19-3
• 化学式: C₁₉H₃₇NO₂S
• 分子量: 343.574
• InChiKey: UAGXAEOOUIMGMG-LTFTZWNVSA-N

物化性质

• 沸点：
  471.3±55.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6S,E)-N-[(S_s)-tert-butanesulfinyl]-6-aminopentadec-3-en-2-one 在 盐酸 、 Wilkinson's catalyst 、 氢气 、 sodium cyanoborohydride 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 乙醇 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成 (+)-(2S,6R)-2-methyl-6-n-nonylpiperidine hydrochloride
  参考文献：
  名称：

  Enantioselective Synthesis of cis- and trans-2-Methyl-6-nonylpiperidines: Alkaloids Solenopsin and Isosolenopsin

  摘要：

  The cross-metathesis of the enantioenriched homoallylic amine 8 (readily accessible by alpha-aminoallylation of decanal) with methyl vinyl ketone using the Hoveyda-Blechert catalyst 10 in presence of 10 mol% of Ti(O-i-Pr)(4) led exclusively to the (E)-enone 11, which by stereoselective reductive amination affords (+)-isosolenopsin (3a) and (+)-solenopsin (4a) with excellent selectivities.

  DOI：

  10.3987/com-12-s(n)27
• 作为产物：
  描述：

  癸醛 在 titanium(IV) isopropylate 、 titanium(IV) tetraethanolate 、 indium 、 Hoveyda-Grubbs catalyst second generation 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 (6S,E)-N-[(S_s)-tert-butanesulfinyl]-6-aminopentadec-3-en-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of cis- and trans-2-Methyl-6-nonylpiperidines: Alkaloids Solenopsin and Isosolenopsin

  摘要：

  The cross-metathesis of the enantioenriched homoallylic amine 8 (readily accessible by alpha-aminoallylation of decanal) with methyl vinyl ketone using the Hoveyda-Blechert catalyst 10 in presence of 10 mol% of Ti(O-i-Pr)(4) led exclusively to the (E)-enone 11, which by stereoselective reductive amination affords (+)-isosolenopsin (3a) and (+)-solenopsin (4a) with excellent selectivities.

  DOI：

  10.3987/com-12-s(n)27

文献信息

• Stereoselective α-Aminoallylation of Aldehydes with Chiral<i>tert</i>-Butanesulfinamides and Allyl Bromides^†
  作者：José C. González-Gómez、Mohamed Medjahdi、Francisco Foubelo、Miguel Yus

  DOI：10.1021/jo101379u

  日期：2010.9.17

  combination of an aldehyde, an allylic bromide, and tert-butanesulfinamide in the presence of indium metal and titanium tetraethoxide allows straightforward access to homoallylamine derivatives in high yields and stereoselectivities. Moreover, the synthetic utility of the enantioenriched homoallylamine derived from n-decanal was illustrated in a concise synthesis of (+)-isosolenopsin. In this context, similar

  在存在铟金属和四乙氧基钛的情况下，将醛，烯丙基溴和叔丁烷亚磺酰胺的组合可以高产率和立体选择性直接获得均烯丙胺衍生物。此外，在（+）-异异视紫红质的简明合成中说明了衍生自n-癸醛的富含对映体的高烯丙胺的合成效用。在这种情况下，其他团体最近在合成天然生物碱中也使用了类似的高烯丙胺。
• Cross-Metathesis of Chiral <i>N</i>-<i>tert</i>-Butylsulfinyl Homoallylamines: Application to the Enantioselective Synthesis of Naturally Occurring 2,6-<i>cis</i>-Disubstituted Piperidines
  作者：Francisco Foubelo、Miguel Yus、José González-Gómez

  DOI：10.1055/s-0028-1083535

  日期：——

  The synthesis of piperidine alkaloids (+)-dihydropinidine (1), (+)-isosolenopsin (2a), (+)-isosolenopsin A (2b), and (2R,6R)-6-methylpipecolic acid (3a) hydrochlorides, based on cross-metathesis of chiral N-tert-butylsulfinyl homoallylamines with methyl vinyl ketone, is presented.

  哌啶生物碱 (+)-二氢哌啶 (1)、(+)-异茄红素 (2a)、(+)-异茄红素 A (2b) 和 (2R,6R)-6-甲基哌啶酸 (3a) 盐酸盐的合成提出了手性 N-叔丁基亚磺酰高烯丙胺与甲基乙烯基酮的交叉复分解反应。
• Enantioselective Synthesis of cis- and trans-2-Methyl-6-nonylpiperidines: Alkaloids Solenopsin and Isosolenopsin
  作者：Miguel Yus、José Carlos González-Gómez、Mohamed Medjahdi、Francisco Foubelo

  DOI：10.3987/com-12-s(n)27

  日期：——

  The cross-metathesis of the enantioenriched homoallylic amine 8 (readily accessible by alpha-aminoallylation of decanal) with methyl vinyl ketone using the Hoveyda-Blechert catalyst 10 in presence of 10 mol% of Ti(O-i-Pr)(4) led exclusively to the (E)-enone 11, which by stereoselective reductive amination affords (+)-isosolenopsin (3a) and (+)-solenopsin (4a) with excellent selectivities.