(R)-(+)-2-methyloctylamine | 89999-54-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-(+)-2-methyloctylamine
• 英文别名: (2R)-2-methyloctan-1-amine
• CAS: 89999-54-2
• 化学式: C₉H₂₁N
• 分子量: 143.272
• InChiKey: QSVVOTNSTSRPQJ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-methyloctylamine 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以0.19 g的产率得到(R)-2-methyloctylamine hydrochloride
  参考文献：
  名称：

  Probing the Limits of the Majority-Rules Principle in a Dynamic Supramolecular Polymer

  摘要：

  By systematic variation of the chemical structure of benzene-1,3,5-tricarboxamide (BTA) derivatives, the effect of chemical structure on the amplification of chirality was studied and quantified. In combination with temperature-dependent amplification experiments, the limits of the majority-rules principle were also investigated. For all BTA derivatives a high, constant helix reversal penalty was determined, which is related to the intermolecular hydrogen bonds that are present in all studied derivatives. For asymmetrically substituted BTA derivatives an odd-even effect was found in the degree of chiral amplification when changing the position of the stereogenic center with respect to the amide functionality. It was found that the mismatch penalty could be directly related to the number of stereocenters present in the molecules. Increasing this number from one to three resulted in an increase in this energy penalty while leaving the helix reversal penalty unaffected. For the majority-rules principle this implies that a single stereocenter present in the molecule contains sufficient chiral information at the molecular level to result in a chirally amplified state at the supramolecular level. Further evidence that the mismatch penalty is directly related to the number of stereocenters was obtained from mixed majority-rules experiments where two BTA derivatives with different numbers of stereocenters with opposite stereoconfiguration were studied in a majority-rules experiment. Finally, the ultimate limits of chiral amplification for the majority-rules principle were investigated, revealing that, given a certain helix reversal penalty, there is an optimum to which the mismatch penalty can be reduced while also enhancing the degree of chiral amplification. Temperature-dependent majority-rules experiments could indeed confirm these simulations. These findings show the relevance of both energy penalties when trying to enhance the degree of chiral amplification for the majority-rules principle in a one-dimensional helical supramolecular polymer.

  DOI：

  10.1021/ja9080875
• 作为产物：
  描述：

  (2S)-2-(methoxymethyl)-N-[(2R)-2-methyloctyl]pyrrolidin-1-amine 以56%的产率得到
  参考文献：
  名称：

  ENDERS, D.;SCHUBERT, H., ANGEW. CHEM., 1984, 96, N 5, 368-369

  摘要：

  DOI：

文献信息

• Asymmetrically Substituted Benzene-1,3,5-tricarboxamides: Self-Assembly and Odd-Even Effects in the Solid State and in Dilute Solution
  作者：Patrick J. M. Stals、Maarten M. J. Smulders、Rafael Martín-Rapún、Anja R. A. Palmans、E. W. Meijer

  DOI：10.1002/chem.200802196

  日期：2009.2.16

  organization: Chiral benzene tricarboxamides with methyl substituents at defined positions self‐assemble into supramolecular polymers of preferred helicity by three‐fold α‐helical‐type hydrogen bonding. The odd–even effect is operative and all derivatives are liquid crystalline showing a Colho phase (see figure).

  分子组织：在指定位置具有甲基取代基的手性苯三甲酰胺通过三倍的α螺旋型氢键自组装成具有优选螺旋度的超分子聚合物。奇-偶效应可操作和所有衍生物是示出山口液晶浩相（见图）。
• Enders, Dieter; Schubert, Heinrich, Angewandte Chemie, 1984, vol. 96, # 5, p. 368 - 369
  作者：Enders, Dieter、Schubert, Heinrich

  DOI：——

  日期：——
• OHTA, HIROMICHI;KOBAYASHI, NAOKI;OZAKI, KAZUHIKO, J. ORG. CHEM., 54,(1989) N, C. 1802-1804
  作者：OHTA, HIROMICHI、KOBAYASHI, NAOKI、OZAKI, KAZUHIKO

  DOI：——

  日期：——
• Probing the Limits of the Majority-Rules Principle in a Dynamic Supramolecular Polymer
  作者：Maarten M. J. Smulders、Patrick J. M. Stals、Tristan Mes、Tim F. E. Paffen、Albertus P. H. J. Schenning、Anja R. A. Palmans、E. W. Meijer

  DOI：10.1021/ja9080875

  日期：2010.1.20

  By systematic variation of the chemical structure of benzene-1,3,5-tricarboxamide (BTA) derivatives, the effect of chemical structure on the amplification of chirality was studied and quantified. In combination with temperature-dependent amplification experiments, the limits of the majority-rules principle were also investigated. For all BTA derivatives a high, constant helix reversal penalty was determined, which is related to the intermolecular hydrogen bonds that are present in all studied derivatives. For asymmetrically substituted BTA derivatives an odd-even effect was found in the degree of chiral amplification when changing the position of the stereogenic center with respect to the amide functionality. It was found that the mismatch penalty could be directly related to the number of stereocenters present in the molecules. Increasing this number from one to three resulted in an increase in this energy penalty while leaving the helix reversal penalty unaffected. For the majority-rules principle this implies that a single stereocenter present in the molecule contains sufficient chiral information at the molecular level to result in a chirally amplified state at the supramolecular level. Further evidence that the mismatch penalty is directly related to the number of stereocenters was obtained from mixed majority-rules experiments where two BTA derivatives with different numbers of stereocenters with opposite stereoconfiguration were studied in a majority-rules experiment. Finally, the ultimate limits of chiral amplification for the majority-rules principle were investigated, revealing that, given a certain helix reversal penalty, there is an optimum to which the mismatch penalty can be reduced while also enhancing the degree of chiral amplification. Temperature-dependent majority-rules experiments could indeed confirm these simulations. These findings show the relevance of both energy penalties when trying to enhance the degree of chiral amplification for the majority-rules principle in a one-dimensional helical supramolecular polymer.
• ENDERS, D.;SCHUBERT, H., ANGEW. CHEM., 1984, 96, N 5, 368-369
  作者：ENDERS, D.、SCHUBERT, H.

  DOI：——

  日期：——