methyl (N,N-dimethylamino)(1-methyl-3-phenylpropyl)carbamate | 145803-15-2

• 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: methyl (N,N-dimethylamino)(1-methyl-3-phenylpropyl)carbamate
• 英文别名: methyl N-(dimethylamino)-N-(4-phenylbutan-2-yl)carbamate
• CAS: 145803-15-2
• 化学式: C₁₄H₂₂N₂O₂
• 分子量: 250.341
• InChiKey: YCLUBSFRASJFDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (N,N-dimethylamino)(1-methyl-3-phenylpropyl)carbamate 在 氨 、 lithium 作用下， 反应 2.0h， 以84%的产率得到N-(methoxycarbonyl)-2-amino-4-phenylbutane
  参考文献：
  名称：

  Lithium/ammonia cleavage of the nitrogen-nitrogen bond in N-(methoxycarbonyl)- and N-acetylhydrazines

  摘要：

  DOI：

  10.1021/jo00312a034
• 作为产物：
  描述：

  苯丙醛 在 cerium(III) chloride 作用下， 反应 30.0h， 生成 methyl (N,N-dimethylamino)(1-methyl-3-phenylpropyl)carbamate
  参考文献：
  名称：

  Organocerium additions to hydrazones: effects of reagent stoichiometry on efficiency and selectivity

  摘要：

  The effects of reagent stoichiometry on the efficiency and selectivity of organocerium additions to chiral and achiral hydrazones have been investigated. rhe reagent formed in-situ from 1 equiv of CH3Li and 0.33 equiv of CeCl3 adds efficiently (>65% yield) to N,N-dimethylhydrazone 1, but this same reagent reacts only sluggishly with chiral SAMEMP hydrazone 2 (<30% yield). The optimal stoichiometry of the organocerium reagent is 1:1 CH3Li/CeCl3, despite the fact that not all of the CeCl3 ig consumed in the transmetalation. At least 2 equiv of methyl nucleophile is required to obtain acceptable yields in additions to 2, suggesting that the auxiliary side chain inhibits the reactivity of the first equivalent of organometallic reagent and that binding of the reagent to one of the hydrazone nitrogen atoms facilitates addition. This hypothesis is supported by the observation that competitive ligands such as amines or alkoxides effectively inhibit the addition of organocerium reagents to 1. The active reagent formed at all mixing stoichiometries is proposed to be a trimethyllanthanide species on the basis of reactivity and the presence of ur reacted MCl3 at less than 3:1 CH3Li/MCl3 mixing ratios.

  DOI：

  10.1021/jo00055a008

文献信息

• DENMARK, SCOTT E.;NICAISE, OLIVIER;EDWARDS, JAMES P., J. ORG. CHEM., 55,(1990) N5, C. 6219-6223
  作者：DENMARK, SCOTT E.、NICAISE, OLIVIER、EDWARDS, JAMES P.

  DOI：——

  日期：——
• Organocerium additions to hydrazones: effects of reagent stoichiometry on efficiency and selectivity
  作者：Scott E. Denmark、James P. Edwards、Olivier Nicaise

  DOI：10.1021/jo00055a008

  日期：1993.1

  The effects of reagent stoichiometry on the efficiency and selectivity of organocerium additions to chiral and achiral hydrazones have been investigated. rhe reagent formed in-situ from 1 equiv of CH3Li and 0.33 equiv of CeCl3 adds efficiently (>65% yield) to N,N-dimethylhydrazone 1, but this same reagent reacts only sluggishly with chiral SAMEMP hydrazone 2 (<30% yield). The optimal stoichiometry of the organocerium reagent is 1:1 CH3Li/CeCl3, despite the fact that not all of the CeCl3 ig consumed in the transmetalation. At least 2 equiv of methyl nucleophile is required to obtain acceptable yields in additions to 2, suggesting that the auxiliary side chain inhibits the reactivity of the first equivalent of organometallic reagent and that binding of the reagent to one of the hydrazone nitrogen atoms facilitates addition. This hypothesis is supported by the observation that competitive ligands such as amines or alkoxides effectively inhibit the addition of organocerium reagents to 1. The active reagent formed at all mixing stoichiometries is proposed to be a trimethyllanthanide species on the basis of reactivity and the presence of ur reacted MCl3 at less than 3:1 CH3Li/MCl3 mixing ratios.
• Lithium/ammonia cleavage of the nitrogen-nitrogen bond in N-(methoxycarbonyl)- and N-acetylhydrazines
  作者：Scott E. Denmark、Olivier Nicaise、James P. Edwards

  DOI：10.1021/jo00312a034

  日期：1990.12