6-O-(2-anthracenecarbonyl)-α-CD | 1039503-50-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(2-anthracenecarbonyl)-α-CD
• 英文别名: 6-O-(2-anthracenecarbonyl)-α-cyclodextrin；[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31R,32R,33R,34R,35R,36R,37R,38R,39R,40R,41R,42R)-31,32,33,34,35,36,37,38,39,40,41,42-dodecahydroxy-10,15,20,25,30-pentakis(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-5-yl]methyl anthracene-2-carboxylate
• CAS: 1039503-50-8
• 化学式: C₅₁H₆₈O₃₁
• 分子量: 1177.08
• InChiKey: WOGCEYVEBIMIML-RPSOXMBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.4
• 重原子数：
  82
• 可旋转键数：
  9
• 环数：
  25.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  6-O-(2-anthracenecarbonyl)-α-CD 在 cucurbit[8]uril 作用下， 以 水 、 乙二醇 为溶剂， -20.0 ℃ 、200.0 MPa 条件下， 反应 1.0h， 生成 、
  参考文献：
  名称：

  Highly Stereoselective Photocyclodimerization of α-Cyclodextrin-Appended Anthracene Mediated by γ-Cyclodextrin and Cucurbit[8]uril: A Dramatic Steric Effect Operating Outside the Binding Site

  摘要：

  Photocyclodimerization of alpha-cyclodextrin (CD)-appended anthracene was studied in the presence of gamma-CD and cucurbit[8] uril (CB[8]) hosts to manipulate the stereodifferentiating photoreaction occurring inside the cavity by the bulky attachment located outside. The gamma-CD-mediated photodimerization afforded the head-to-tail photodimers in 98% combined yield, in particular, the syn-head-to-tail photodimer of 91% ee in 68% yield, which are much greater than 32% ee and 44% yield obtained with unmodified anthracene carboxylate. The use of CB[8] also led to a striking inversion of the head-to-tail/head-to-head selectivity, affording exclusively the head-to-head photodimers in 99% combined yield.

  DOI：

  10.1021/ja8032923
• 作为产物：
  描述：

  2-蒽羰基氯化 、 α-环糊精 以 吡啶 为溶剂， 反应 2.0h， 以5.3%的产率得到6-O-(2-anthracenecarbonyl)-α-CD
  参考文献：
  名称：

  Highly Stereoselective Photocyclodimerization of α-Cyclodextrin-Appended Anthracene Mediated by γ-Cyclodextrin and Cucurbit[8]uril: A Dramatic Steric Effect Operating Outside the Binding Site

  摘要：

  Photocyclodimerization of alpha-cyclodextrin (CD)-appended anthracene was studied in the presence of gamma-CD and cucurbit[8] uril (CB[8]) hosts to manipulate the stereodifferentiating photoreaction occurring inside the cavity by the bulky attachment located outside. The gamma-CD-mediated photodimerization afforded the head-to-tail photodimers in 98% combined yield, in particular, the syn-head-to-tail photodimer of 91% ee in 68% yield, which are much greater than 32% ee and 44% yield obtained with unmodified anthracene carboxylate. The use of CB[8] also led to a striking inversion of the head-to-tail/head-to-head selectivity, affording exclusively the head-to-head photodimers in 99% combined yield.

  DOI：

  10.1021/ja8032923

文献信息

• Dual Supramolecular Photochirogenesis: Ultimate Stereocontrol of Photocyclodimerization by a Chiral Scaffold and Confining Host
  作者：Cheng Yang、Chenfeng Ke、Wenting Liang、Gaku Fukuhara、Tadashi Mori、Yu Liu、Yoshihisa Inoue

  DOI：10.1021/ja202020x

  日期：2011.9.7

  In contrast to the brilliant success in thermal asymmetric synthesis, precise stereocontrol remains a great challenge in chiral photochemistry because of the lack of effective tools and methodologies for controlling the short-lived, weakly interacting, and highly reactive electronically excited species. In this work, we achieved this goal through the "dual-chiral, dual-supramolecular" photochirogenesis approach, which enabled us to realized dramatic acceleration and perfect stereocontrol in one of the most representative photoreactions. Thus, the [4 + 4] photocyclodimerization of 2-anthracenecarboxylate tethered to an a-cyclodextrin scaffold was accelerated by a gamma-cyclodextrin or cucurbit[8]uril host and gave a single enantiomeric cyclodimer (out of four possible chiral and achiral stereo-isomers) in up to 98% chemical and 99% optical yield.
• Highly Stereoselective Photocyclodimerization of α-Cyclodextrin-Appended Anthracene Mediated by γ-Cyclodextrin and Cucurbit[8]uril: A Dramatic Steric Effect Operating Outside the Binding Site
  作者：Cheng Yang、Tadashi Mori、Yumi Origane、Young Ho Ko、Narayanan Selvapalam、Kimoon Kim、Yoshihisa Inoue

  DOI：10.1021/ja8032923

  日期：2008.7.1

  Photocyclodimerization of alpha-cyclodextrin (CD)-appended anthracene was studied in the presence of gamma-CD and cucurbit[8] uril (CB[8]) hosts to manipulate the stereodifferentiating photoreaction occurring inside the cavity by the bulky attachment located outside. The gamma-CD-mediated photodimerization afforded the head-to-tail photodimers in 98% combined yield, in particular, the syn-head-to-tail photodimer of 91% ee in 68% yield, which are much greater than 32% ee and 44% yield obtained with unmodified anthracene carboxylate. The use of CB[8] also led to a striking inversion of the head-to-tail/head-to-head selectivity, affording exclusively the head-to-head photodimers in 99% combined yield.