5-N-tert-butoxycarbonylaminopentyl (E,E)-2',4'-hexadienoate | 640286-85-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-N-tert-butoxycarbonylaminopentyl (E,E)-2',4'-hexadienoate
• 英文别名: 5-[(2-methylpropan-2-yl)oxycarbonylamino]pentyl (2E,4E)-hexa-2,4-dienoate
• CAS: 640286-85-7
• 化学式: C₁₆H₂₇NO₄
• 分子量: 297.395
• InChiKey: TYZQEUDBGVQNQW-BXROQLSZSA-N

物化性质

• 沸点：
  415.2±28.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-N-tert-butoxycarbonylaminopentyl (E,E)-2',4'-hexadienoate 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-(1-sorbyl-5-aminopentyl)-N',N''-di(n-octyl)benzene-1,3,5-tricarboxamide
  参考文献：
  名称：

  超分子螺旋向聚合物主链转录中的手性扩增。

  摘要：

  DOI：

  10.1002/anie.200462347
• 作为产物：
  描述：

  5-氨基-1-戊醇 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 为溶剂， 反应 3.0h， 生成 5-N-tert-butoxycarbonylaminopentyl (E,E)-2',4'-hexadienoate
  参考文献：
  名称：

  超分子螺旋向聚合物主链转录中的手性扩增。

  摘要：

  DOI：

  10.1002/anie.200462347

文献信息

• Photoinitiated Polymerization of Columnar Stacks of Self-Assembled Trialkyl-1,3,5-benzenetricarboxamide Derivatives
  作者：Mitsutoshi Masuda、Pascal Jonkheijm、Rint P. Sijbesma、E. W. Meijer

  DOI：10.1021/ja037927u

  日期：2003.12.1

  A disk-shaped molecule, N-(5-sorbyl-pentyl)-N',N"-di(n-octyl)benzene-1,3,5-tricarboxamide (1), has been synthesized and assembled into a columnar stack in cyclohexane. Using a photoinitiated process, we polymerized monomer 1 in its self-assembled state and analyzed the resulting poly-1. On cooling a boiling cyclohexane solution of 1, the molecules aggregate via amide hydrogen bonds, as supported by the position of the N-H stretching band in FT-IR spectroscopy. Evidence of helical columnar stacking of 1 in the aggregate is provided by an induced CD effect upon blending 1 with a chiral side-chain homologue 3 in a so-called "sergeants and soldiers" experiment. The columnar assembly in cyclohexane was polymerized by UV light (365 nm) irradiation in the presence of 2,2-dimethoxy-2-phenylacetophenone as radical photoinitiator. The polymerization occurs selectively to give 1,4-polymer with isolated trans C=C bonds, as shown by FT-IR, and H-1 and C-13 NMR spectroscopy. Lack of polymerization of methyl sorbate (4) under identical conditions, and low incorporation of 4 in copolymerizations with 1 in cyclohexane, suggests that the polymerization preferentially occurs within the columnar assembly. Size exclusion chromatography shows that the degree of polymerization (X,) based on number average molecular weight is approximately 65. Incorporation of small amounts of nonpolymerizable derivatives 2 and 3 into the columns has no effect on X, and conversion. Molecular models show that the polymerizable sidearm of 1 is long enough to span the distance between the monomers in the chiral stack. Under the atomic force microscope (AFM), purified samples of polymerized 1 displayed nanometer-sized fibrous morphologies with a high-axial-ratio (> 150), uniform width (60 nm), and a thickness (1.0 nm) which corresponds to the width of the benzene tricarboxamide core of 1, whereas aggregates of nonpolymerized 1 yield a featureless image due to their instability.
• Chiral Amplification in the Transcription of Supramolecular Helicity into a Polymer Backbone
  作者：Andrew J. Wilson、Mitsutoshi Masuda、Rint P. Sijbesma、E. W. Meijer

  DOI：10.1002/anie.200462347

  日期：2005.4.8