2,4-dimethyl-3-(benzyltosylamino)-1,4-pentadiene | 131544-28-0

• 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: 2,4-dimethyl-3-(benzyltosylamino)-1,4-pentadiene
• 英文别名: N-benzyl-N-(2,4-dimethylpenta-1,4-dien-3-yl)-4-methylbenzenesulfonamide
• CAS: 131544-28-0
• 化学式: C₂₁H₂₅NO₂S
• 分子量: 355.501
• InChiKey: NSEVVADMSOXSTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-3-(benzyltosylamino)-1,4-pentadiene 在 乙醇 、 双氧水 、 sodium acetate 、 儿萘酚硼烷 作用下， 生成 2,4-dimethyl-3-(benzyltosylamino)-1-pentene 、 2,4-dimethyl-1-hydroxy-3-(benzyltosylamino)-4-pentene
  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：

  N-tosyl-2-methylpropenimine 在 sodium hydride 、 magnesium 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.42h， 生成 2,4-dimethyl-3-(benzyltosylamino)-1,4-pentadiene
  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

• BURGESS, K.;OHLMEYER, M. J., J. ORG. CHEM., 56,(1991) N, C. 1027-1036
  作者：BURGESS, K.、OHLMEYER, M. J.

  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.