2-methyl-3-(N-tosylamino)-1-heptene | 90036-68-3

• 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: 2-methyl-3-(N-tosylamino)-1-heptene
• 英文别名: 4-Methyl-N-(2-methylhept-1-en-3-yl)benzene-1-sulfonamide；4-methyl-N-(2-methylhept-1-en-3-yl)benzenesulfonamide
• CAS: 90036-68-3
• 化学式: C₁₅H₂₃NO₂S
• 分子量: 281.419
• InChiKey: BNFHDYURZBTLCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(N-tosylamino)-1-heptene 在 四丁基碘化铵 sodium hydroxide 、 硼烷四氢呋喃络合物 、 乙醇 、 双氧水 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 86.0h， 生成 syn-2-methyl-3-(benzyltosylamino)-1-heptanol
  参考文献：
  名称：

  Manipulation of substrate-controlled diastereoselectivities in hydroborations of acyclic allylamine derivatives

  摘要：

  Racemic, and optically active, 2-methyl-3-(N-tosylamino)alkenes I were prepared and subjected to both catalyzed and uncatalyzed hydroborations. Data obtained for the catalyzed hydroborations of these allylamine derivatives are consistent with the theory of secondary orbital interactions in transition metal mediated processes presented in the preceding paper. Surprisingly, diastereoselectivities for conventional (uncatalyzed) hydroborations of the same substrates can be extremely sensitive to the borane used; anti products result when borane-tetrahydrofuran complex is reacted with substrates I (R' = Bn), while with 9-BBN (9-borabicyclo[3.3.1]nonane) these reactions are syn selective. Some of these results are contrary to expectations based upon experimental and theoretical data in the current literature for hydroboration of allylic alcohols. Methodology described in this paper facilitates syntheses of amine alcohols II with extremely high syn and anti selectivities.

  DOI：

  10.1021/jo00003a024
• 作为产物：
  描述：

  对甲苯磺酰胺 在 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.83h， 生成 2-methyl-3-(N-tosylamino)-1-heptene
  参考文献：
  名称：

  Manipulation of substrate-controlled diastereoselectivities in hydroborations of acyclic allylamine derivatives

  摘要：

  Racemic, and optically active, 2-methyl-3-(N-tosylamino)alkenes I were prepared and subjected to both catalyzed and uncatalyzed hydroborations. Data obtained for the catalyzed hydroborations of these allylamine derivatives are consistent with the theory of secondary orbital interactions in transition metal mediated processes presented in the preceding paper. Surprisingly, diastereoselectivities for conventional (uncatalyzed) hydroborations of the same substrates can be extremely sensitive to the borane used; anti products result when borane-tetrahydrofuran complex is reacted with substrates I (R' = Bn), while with 9-BBN (9-borabicyclo[3.3.1]nonane) these reactions are syn selective. Some of these results are contrary to expectations based upon experimental and theoretical data in the current literature for hydroboration of allylic alcohols. Methodology described in this paper facilitates syntheses of amine alcohols II with extremely high syn and anti selectivities.

  DOI：

  10.1021/jo00003a024

文献信息

• Synthesis of protected allylic amines from allylic phenyl selenides: Improved conditions for the chloramine T oxidation of allylic phenyl selenides
  作者：John E. Fankhauser、Richard M. Peevey、Paul B. Hopkins

  DOI：10.1016/s0040-4039(01)91136-0

  日期：1984.1

  Anhydrous chloramine T in methanol is a highly effective reagent for the conversion of allylic phenyl selenides to the corresponding rearranged N-allylic-p-toluenesulfonamides. The reaction presumably proceeds via an allylic selenimide intermediate which undergoes [2,3]-sigmatropic rearrangement.

  甲醇中的无水氯胺T是将烯丙基苯基硒化物转化为相应的重排N-烯丙基-对甲苯磺酰胺的高效试剂。该反应大概是通过烯丙基硒酰亚胺中间体进行的，该中间体经历了[2,3]-σ重排。
• BURGESS, K.;OHLMEYER, M. J., J. ORG. CHEM., 56,(1991) N, C. 1027-1036
  作者：BURGESS, K.、OHLMEYER, M. J.

  DOI：——

  日期：——
• PANKHAUSER, J. E.;PEEVEY, R. M.;HOPKINS, P. B., TETRAHEDRON LETT., 1984, 25, N 1, 15-18
  作者：PANKHAUSER, J. E.、PEEVEY, R. M.、HOPKINS, P. B.

  DOI：——

  日期：——
• Manipulation of substrate-controlled diastereoselectivities in hydroborations of acyclic allylamine derivatives
  作者：Kevin Burgess、Michael J. Ohlmeyer

  DOI：10.1021/jo00003a024

  日期：1991.2

  Racemic, and optically active, 2-methyl-3-(N-tosylamino)alkenes I were prepared and subjected to both catalyzed and uncatalyzed hydroborations. Data obtained for the catalyzed hydroborations of these allylamine derivatives are consistent with the theory of secondary orbital interactions in transition metal mediated processes presented in the preceding paper. Surprisingly, diastereoselectivities for conventional (uncatalyzed) hydroborations of the same substrates can be extremely sensitive to the borane used; anti products result when borane-tetrahydrofuran complex is reacted with substrates I (R' = Bn), while with 9-BBN (9-borabicyclo[3.3.1]nonane) these reactions are syn selective. Some of these results are contrary to expectations based upon experimental and theoretical data in the current literature for hydroboration of allylic alcohols. Methodology described in this paper facilitates syntheses of amine alcohols II with extremely high syn and anti selectivities.