2-cinnamoyl-α-cyclodextrin | 1159217-70-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-cinnamoyl-α-cyclodextrin
• 英文别名: 2-trans-CiO-α-CD；2-CiO-α-CD；[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,32R,33R,34R,35R,36R,37R,38R,39R,40R,41R,42R)-31,33,34,35,36,37,38,39,40,41,42-undecahydroxy-5,10,15,20,25,30-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29-dodecaoxaheptacyclo[26.2.2.23,6.28,11.213,16.218,21.223,26]dotetracontan-32-yl] (E)-3-phenylprop-2-enoate
• CAS: 1159217-70-5
• 化学式: C₄₅H₆₆O₃₁
• 分子量: 1103.0
• InChiKey: GFYZGRZYHMHUNK-FQIKRZBOSA-N

物化性质

• 沸点：
  1428.1±65.0 °C(predicted)
• 密度：
  1.76±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -10.2
• 重原子数：
  76
• 可旋转键数：
  10
• 环数：
  23.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  481
• 氢给体数：
  17
• 氢受体数：
  31

反应信息

• 作为反应物：
  描述：

  2-cinnamoyl-α-cyclodextrin 以 water-d2 为溶剂， 生成
  参考文献：
  名称：

  Social Self-Sorting: Alternating Supramolecular Oligomer Consisting of Isomers

  摘要：

  The isomers of cinnamoyl alpha-CDs (2-CiO-alpha-CD and 3-CiO-alpha-CD) organize by themselves to give different types of supramolecular complexes in aqueous solutions. 2-CiO-alpha-CD was found to form a double-threaded dimer, which was characterized by single crystal X-ray analysis. The molecular sizes of supramolecular complexes consisting of CiO-alpha-CDs were estimated by pulsed field gradient spin-echo NMR, which gives the diffusion coefficient (D). D of 2-CiO-alpha-CD was found to be 2.3 x 10(-10) m(2)/s at concentrations over 10 mM and D was saturated. It should be noted that the hydrodynamic radius derived from D of 2-CiO-alpha-CD was found to be 9.6 angstrom, which closely matched the result from the single crystal X-ray analysis. D of 3-CiO-alpha-CD, however, was smaller than that of 2-CiO-alpha-CD at concentrations over 32 mM, indicating that 3-CiO-alpha-CD formed a supramolecular oligomer. Two-dimensional (2D)-ROESY spectra of the mixture of 2-CiO-alpha-CD and 3-CiO-alpha-CD did not show a correlation between the same species; rather, correlation peaks between 2-CiO-alpha-CD and 3-CiO-alpha-CD were observed. D's of a mixture of 2-CiO-alpha-CD and 3-CiO-alpha-CD were found to be larger than those of 2-CiO-alpha-CD and 3-CiO-alpha-CD, respectively, indicating that the mixture of 2-CiO-alpha-CD and 3-CiO-alpha-CD formed an alternative supramolecular oligomer and not a self- or random- supramolecular complex. CDs recognize a guest molecule and the substitutional position of a guest molecule on CD, suggesting that CDs have social self-sorting capability.

  DOI：

  10.1021/ja903988c
• 作为产物：
  描述：

  3-Nitrophenyl cinnamate 、 α-环糊精 在 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 生成 2-cinnamoyl-α-cyclodextrin 、 3-cinnamoyl-α-cyclodextrin
  参考文献：
  名称：

  Switching of polymerization activity of cinnamoyl-α-cyclodextrin

  摘要：

  肉桂酰 α-环糊精 (α-CD) 已被发现能够引发 δ-戊内酯 (δ-VL) 的聚合，从而产生高产率的聚合物。通过肉桂酰基的存在，δ-VL 的羰基氧和 CD 的羟基之间形成氢键，从而激活单体，这是通过 FT-IR 测量观察到的。然而，α-CD C3-和C6-位上的肉桂酰基并不影响聚合能力。仅C2位表现出高聚合活性。聚合活性可以通过连接到α-CD 边缘的肉桂酰基的光异构化来切换。光异构化改变了α-CD 腔活性位点中的特定单体识别和聚合。

  DOI：

  10.1039/b818241h

文献信息

• Social Self-Sorting: Alternating Supramolecular Oligomer Consisting of Isomers
  作者：Naoki Tomimasu、Akira Kanaya、Yoshinori Takashima、Hiroyasu Yamaguchi、Akira Harada

  DOI：10.1021/ja903988c

  日期：2009.9.2

  The isomers of cinnamoyl alpha-CDs (2-CiO-alpha-CD and 3-CiO-alpha-CD) organize by themselves to give different types of supramolecular complexes in aqueous solutions. 2-CiO-alpha-CD was found to form a double-threaded dimer, which was characterized by single crystal X-ray analysis. The molecular sizes of supramolecular complexes consisting of CiO-alpha-CDs were estimated by pulsed field gradient spin-echo NMR, which gives the diffusion coefficient (D). D of 2-CiO-alpha-CD was found to be 2.3 x 10(-10) m(2)/s at concentrations over 10 mM and D was saturated. It should be noted that the hydrodynamic radius derived from D of 2-CiO-alpha-CD was found to be 9.6 angstrom, which closely matched the result from the single crystal X-ray analysis. D of 3-CiO-alpha-CD, however, was smaller than that of 2-CiO-alpha-CD at concentrations over 32 mM, indicating that 3-CiO-alpha-CD formed a supramolecular oligomer. Two-dimensional (2D)-ROESY spectra of the mixture of 2-CiO-alpha-CD and 3-CiO-alpha-CD did not show a correlation between the same species; rather, correlation peaks between 2-CiO-alpha-CD and 3-CiO-alpha-CD were observed. D's of a mixture of 2-CiO-alpha-CD and 3-CiO-alpha-CD were found to be larger than those of 2-CiO-alpha-CD and 3-CiO-alpha-CD, respectively, indicating that the mixture of 2-CiO-alpha-CD and 3-CiO-alpha-CD formed an alternative supramolecular oligomer and not a self- or random- supramolecular complex. CDs recognize a guest molecule and the substitutional position of a guest molecule on CD, suggesting that CDs have social self-sorting capability.
• Switching of polymerization activity of cinnamoyl-α-cyclodextrin
  作者：Motofumi Osaki、Yoshinori Takashima、Hiroyasu Yamaguchi、Akira Harada

  DOI：10.1039/b818241h

  日期：——

  Cinnamoyl α-cyclodextrin (α-CD) has been found to initiate polymerization of δ-valerolactone (δ-VL) to give a polymer in high yield. By the presence of the cinnamoyl group, hydrogen bond was formed between the carbonyl oxygen of δ-VL and the hydroxyl group of CD to activate the monomer, which was observed by FT-IR measurements. However, the cinnamoyl group at the C3- and C6-positions of α-CD did not affect the polymerization ability. Only that of the C2-position showed high polymerization activity. The polymerization activity could be switched by the photoisomerization of the cinnamoyl group attached to the rim of α-CD. Specific monomer recognition and polymerization in the active site of the α-CD cavity was changed by the photoisomerization.

  肉桂酰 α-环糊精 (α-CD) 已被发现能够引发 δ-戊内酯 (δ-VL) 的聚合，从而产生高产率的聚合物。通过肉桂酰基的存在，δ-VL 的羰基氧和 CD 的羟基之间形成氢键，从而激活单体，这是通过 FT-IR 测量观察到的。然而，α-CD C3-和C6-位上的肉桂酰基并不影响聚合能力。仅C2位表现出高聚合活性。聚合活性可以通过连接到α-CD 边缘的肉桂酰基的光异构化来切换。光异构化改变了α-CD 腔活性位点中的特定单体识别和聚合。