N-methyl-2-(hydroxymethyl)-3,3-dimethylbutylamine | 116005-24-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-methyl-2-(hydroxymethyl)-3,3-dimethylbutylamine
• 英文别名: 3,3-Dimethyl-2-(methylaminomethyl)butan-1-ol
• CAS: 116005-24-4
• 化学式: C₈H₁₉NO
• mdl: MFCD19220193
• 分子量: 145.245
• InChiKey: SFUAZIRSNPTKCT-UHFFFAOYSA-N

物化性质

• 沸点：
  210.1±23.0 °C(Predicted)
• 密度：
  0.867±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-2-(hydroxymethyl)-3,3-dimethylbutylamine 在 三乙胺 、 三氯化磷 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以57%的产率得到2-Chloro-3-methyl-5-tert-butyl-1,3,2-oxazaphosphorinane
  参考文献：
  名称：

  Study of the Conformational Equilibria of 2-Z-3-Methyl-1,3,2-oxazaphosphorinanes. Steric and Stereoelectronic Influences on the Orientation of the Me2N Substituent on Three-Coordinate Phosphorus

  摘要：

  The conformations of a series of 1,3,2-oxazaphosphorinanes containing three-coordinate phosphorus, 1-9, have been determined by the use of H-1, P-31, and C-13 NMR spectroscopy. The rings were substituted at ring nitrogen, N(3), with a methyl group to compare its effect on conformational energies with those of 1,3,2-oxazaphosphorinanes reported earlier that featured a larger substituent at N(3), Ph or i-Pr. Quite expectedly, like those rings previously studied with Ph or i-Pr at N(3), a MeO or (CF3)(2)CHO substituent at phosphorus has a strong preference to be axial on a chair-form ring, 1-4, cis-7, and cis-8, or pseudoaxial on a ring in a twist/boat conformation, trans-7. However, when Me(2)N is attached to phosphorus, the newly studied N(3)Me rings display a chair-chair conformational equilibrium, 10 reversible arrow 11, with the Me(2)N equatorial ring, 11, mildly dominant (58/42, 5; 65/35, 6). This contrasts with ratios of 17/83 and 20/80 for the corresponding N(3)Ph analogs, A, and 23/77 for the N(S)-i-Pr compound, B. The observed change in the free energy of the equilibrium 10 reversible arrow 11, 1.2-1.3 kcal/mol, is ascribed to the dominant influence of a decrease in repulsion experienced in conformation 11 between the equatorial Me(2)NP and the smaller Me at N(3)(Me(2)N(eq)/N(3)Me destabilization) compared to that experienced with the N(3)Ph and N(3)-i-Pr analogs. This steric influence of N(3) substituents on the equilibrium 10 reversible arrow 11 is opposite to that found for four-coordinate phosphorus containing 1,3,2-oxazaphosphorinanes in which Me(2)NP(ax/N(3)Ph repulsions that destabilize 10 appear to be dominant.

  DOI：

  10.1021/jo00120a020
• 作为产物：
  描述：

  N-methyl-2-(carbethoxy)-3,3-dimethylbutyramide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 48.0h， 以71%的产率得到N-methyl-2-(hydroxymethyl)-3,3-dimethylbutylamine
  参考文献：
  名称：

  Conformations of saturated six-membered ring phosphorus heterocycles. 2-Aryl-1,3,2-.lambda.5-oxazaphosphorinanes

  摘要：

  DOI：

  10.1021/ja00229a027

文献信息

• Conformations of saturated six-membered ring phosphorus heterocycles. 2-Aryl-1,3,2-.lambda.5-oxazaphosphorinanes
  作者：Wesley G. Bentrude、William N. Setzer、Alan E. Sopchik、Subramanian. Chandrasekaran、Michael T. Ashby

  DOI：10.1021/ja00229a027

  日期：1988.10
• Study of the Conformational Equilibria of 2-Z-3-Methyl-1,3,2-oxazaphosphorinanes. Steric and Stereoelectronic Influences on the Orientation of the Me2N Substituent on Three-Coordinate Phosphorus
  作者：Yande Huang、Jaehoon Yu、Wesley G. Bentrude

  DOI：10.1021/jo00120a020

  日期：1995.7

  The conformations of a series of 1,3,2-oxazaphosphorinanes containing three-coordinate phosphorus, 1-9, have been determined by the use of H-1, P-31, and C-13 NMR spectroscopy. The rings were substituted at ring nitrogen, N(3), with a methyl group to compare its effect on conformational energies with those of 1,3,2-oxazaphosphorinanes reported earlier that featured a larger substituent at N(3), Ph or i-Pr. Quite expectedly, like those rings previously studied with Ph or i-Pr at N(3), a MeO or (CF3)(2)CHO substituent at phosphorus has a strong preference to be axial on a chair-form ring, 1-4, cis-7, and cis-8, or pseudoaxial on a ring in a twist/boat conformation, trans-7. However, when Me(2)N is attached to phosphorus, the newly studied N(3)Me rings display a chair-chair conformational equilibrium, 10 reversible arrow 11, with the Me(2)N equatorial ring, 11, mildly dominant (58/42, 5; 65/35, 6). This contrasts with ratios of 17/83 and 20/80 for the corresponding N(3)Ph analogs, A, and 23/77 for the N(S)-i-Pr compound, B. The observed change in the free energy of the equilibrium 10 reversible arrow 11, 1.2-1.3 kcal/mol, is ascribed to the dominant influence of a decrease in repulsion experienced in conformation 11 between the equatorial Me(2)NP and the smaller Me at N(3)(Me(2)N(eq)/N(3)Me destabilization) compared to that experienced with the N(3)Ph and N(3)-i-Pr analogs. This steric influence of N(3) substituents on the equilibrium 10 reversible arrow 11 is opposite to that found for four-coordinate phosphorus containing 1,3,2-oxazaphosphorinanes in which Me(2)NP(ax/N(3)Ph repulsions that destabilize 10 appear to be dominant.