2,4-dimethyl-3-(N-tosylamino)-1,4-pentadiene | 131544-26-8

• 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-(N-tosylamino)-1,4-pentadiene
• 英文别名: N-(2,4-dimethylpenta-1,4-dien-3-yl)-4-methylbenzenesulfonamide
• CAS: 131544-26-8
• 化学式: C₁₄H₁₉NO₂S
• 分子量: 265.376
• InChiKey: RVYZIGASYTZHJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2,4-dimethyl-3-(N-tosylamino)-1,4-pentadiene 在 乙醇 、 双氧水 、 sodium acetate 、 sodium hydride 、 儿萘酚硼烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 2,4-dimethyl-3-(benzyltosylamino)-1-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：

  对甲苯磺酰胺 在 四氯化钛 、 magnesium 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.92h， 生成 2,4-dimethyl-3-(N-tosylamino)-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

• <i>Endo</i>-Selective Enyne Ring-Closing Metathesis Promoted by Stereogenic-at-Mo Monoalkoxide and Monoaryloxide Complexes. Efficient Synthesis of Cyclic Dienes Not Accessible through Reactions with Ru Carbenes
  作者：Yeon-Ju Lee、Richard R. Schrock、Amir H. Hoveyda

  DOI：10.1021/ja904098h

  日期：2009.8.5

  Mo-catalyzed reactions afford the endo product exclusively. The efficiency of synthesis of N- and O-containing endo diene heterocycles can be improved significantly through structural modification of Mo catalysts. The modularity of Mo-based monopyrrolides is thus exploited in the identification of the most effective catalyst variants. Through alteration of O-based monodentate ligands, catalysts have been identified

  Stereogenic-at-Mo单烷氧化物和单芳基氧化物复合物促进烯炔闭环复分解（RCM）反应，提供具有高选择性（通常> 98：< 2内：外）的相应内产物。所有催化剂都可以原位制备和使用。五元环、六元环和七元环是通过与带有全碳系链以及含有杂原子取代基的烯炔底物反应获得的。新开发的催化方案补充了相关的外选择性 Ru 催化过程。在基于 Ru 的配合物无差别地提供外向和内向产物的情况下，例如当生成四取代的环烯烃时，钼催化反应仅提供内向产物。通过Mo催化剂的结构改性可以显着提高含N和O的内二烯杂环的合成效率。因此，基于钼的单吡咯烷的模块化被用于鉴定最有效的催化剂变体。通过改变基于 O 的单齿配体，已确定催化剂可以提高烯炔 RCM 的效率。通过 X 射线晶体学阐明了三种 Mo 配合物的结构属性。报道了催化对映选择性烯炔 RCM 反应的第一个例子（高达 98:2 的对映体比例和 >98% 的内）。已经鉴定出能够以更高的效率促进烯炔
• 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.