(1S,2R,9S,10R)-heptacyclo[8.6.6.62,9.03,8.011,16.017,22.023,28]octacosa-3(8),4,6,11(16),12,14,17,19,21,23,25,27-dodecaene-5,13-dicarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (1S,2R,9S,10R)-heptacyclo[8.6.6.62,9.03,8.011,16.017,22.023,28]octacosa-3(8),4,6,11(16),12,14,17,19,21,23,25,27-dodecaene-5,13-dicarboxylate
• 化学式: C₃₀H₁₈O₄
• 分子量: 442.471
• InChiKey: KOKNRFKRYVACHY-YVHASNINSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-蒽甲酸 在 sodium hydroxide 、 human serum albumin 作用下， 以 aq. phosphate buffer 、 水 为溶剂， 反应 1.0h， 生成 (1R,2R,9S,10S)-heptacyclo[8.6.6.62,9.03,8.011,16.017,22.023,28]octacosa-3(8),4,6,11(16),12,14,17,19,21,23,25,27-dodecaene-5,13-dicarboxylate 、 (1R,2R,9S,10S)-heptacyclo[8.6.6.62,9.03,8.011,16.017,22.023,28]octacosa-3(8),4,6,11(16),12,14,17,19,21,23,25,27-dodecaene-5,14-dicarboxylate 、 (1S,2R,9S,10R)-heptacyclo[8.6.6.62,9.03,8.011,16.017,22.023,28]octacosa-3(8),4,6,11(16),12,14,17,19,21,23,25,27-dodecaene-5,13-dicarboxylate
  参考文献：
  名称：

  Highly enantiodifferentiating site of human serum albumin for mediating photocyclodimerization of 2-anthracenecarboxylate elucidated by site-specific inhibition/quenching with xenon

  摘要：

  Complementary to the previous assignment of the first, second, and fourth binding sites of human serum albumin (HSA) for 2-anthracenecarboxylate (AC) and the subsequent mediation of AC photocyclodimerization, the site-specific inhibition of the enantiodifferentiation by xenon allowed us to assign the remaining third and fifth AC-binding sites to subdomains IB and IIIB, respectively. This study reveals a clearer picture of the binding and photochirogenic behavior of HSA and further expands the scope of biosupramolecular photochirogenesis. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2015.12.019

文献信息

• Photocatalytic Supramolecular Enantiodifferentiating Dimerization of 2-Anthracenecarboxylic Acid through Triplet–Triplet Annihilation
  作者：Ming Rao、Kuppusamy Kanagaraj、Chunying Fan、Jiecheng Ji、Chao Xiao、Xueqin Wei、Wanhua Wu、Cheng Yang

  DOI：10.1021/acs.orglett.8b00520

  日期：2018.3.16

  Visible-light-driven enantiodifferentiating photodimerization of 2-anthracenecarboxylic acid (AC) sensitized by Schiff base Pt(II) complex-grafted γ-cyclodextrins leads the first triplet–triplet annihilation-based catalytic photochirogenesis. The syn-head-to-tail (HT) photodimer 2 was achieved in up to 31.4% ee at 61.0% conversion in the presence of 0.5% equiv of the photocatalyst.

  席夫碱Pt（II）复合物嫁接的γ-环糊精敏化的可见光驱动的2-蒽羧酸（AC）的对映体光致二聚化导致了第一个基于三重态-三重态an灭的催化光致化学反应。所述顺式头-尾（HT）photodimer 2是在高达31.4％ee的在61.0％的转化率在光催化剂的0.5％当量的存在下实现的。
• Supramolecular Photochirogenesis Driven by Higher-Order Complexation: Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate to Slipped Cyclodimers via a 2:2 Complex with β-Cyclodextrin
  作者：Xueqin Wei、Wanhua Wu、Ryohei Matsushita、Zhiqiang Yan、Dayang Zhou、Jason J. Chruma、Masaki Nishijima、Gaku Fukuhara、Tadashi Mori、Yoshihisa Inoue、Cheng Yang

  DOI：10.1021/jacs.7b12085

  日期：2018.3.21

  enantioselective, has long been overlooked in foregoing studies but is dominant in reality and is absolutely supramolecularly activated by 2:2 complexation of AC with β-CD. The intricate structural and photophysical aspects of this higher-order complexation-triggered process have been comprehensively elucidated, while the absolute configurations of the slipped cyclodimers have been unambiguously assigned

  在 β-环糊精 (β-CD) 介导的 2-蒽羧酸 (AC) 超分子光环二聚反应中，手性滑动 5,8:9',10'-环二聚体优先于经典的 9,10:9',10'-环二聚体产生。这种通向滑动环二聚体的光致变色途径，完全头对尾（HT）和高度对映选择性，长期以来在前述研究中被忽视，但在现实中占主导地位，并且通过 AC 与 β-CD 的 2:2 络合绝对超分子激活。已经全面阐明了这种高阶络合触发过程的复杂结构和光物理方面，同时通过比较实验和理论圆二色光谱明确指定了滑移环二聚体的绝对构型。在 2:2 复合体中，装在双 β-CD 胶囊中的两个 AC 彼此并未完全重叠，而仅以滑动的抗或同步 HT 方式部分堆叠。因此，它们在光激发时不会自发环二聚化，而是在比单体荧光稍长的波长下发出长寿命的准分子荧光，表明滑移的准分子在构象和能量上既不是极富反应性的，也不是完全松弛的。由于软胶囊中AC对的滑移构象，随后的光环
• pH-Controlled Chirality Inversion in Enantiodifferentiating Photocyclodimerization of 2-Antharacenecarboxylic Acid Mediated by γ-Cyclodextrin Derivatives
  作者：Kuppusamy Kanagaraj、Wenting Liang、Ming Rao、Jiabin Yao、Wanhua Wu、Guo Cheng、Jiecheng Ji、Xueqin Wei、Chao Peng、Cheng Yang

  DOI：10.1021/acs.orglett.0c01194

  日期：2020.7.17

  derivatives were used as chiral hosts for the photocyclodimerization of 2-anthracenecarboxylic acid (AC). The effect of pH on photoreactivity and stereochemical outcome of photoproducts was investigated. Upon changing the solution pH, the stereochemical outcome of HH cyclodimer 3 was inverted from 25.2% to −64.4% and 41.2% to −76.2%, respectively, in the photocyclodimerization of AC mediated by bis-quinoline-modified

  几种γ-环糊精（γ-CDx）衍生物被用作手性主体，用于2-蒽羧酸（AC）的光环二聚。研究了pH对光产物光反应性和立体化学结果的影响。在改变溶液的pH值，HH的cyclodimer的立体化学结果3从分别25.2％至-64.4％和41.2％至-76.2％，反转时，在AC的介导photocyclodimerization双-喹啉改性γ-CDx将7和其N-甲基化衍生物8。
• An Ultimate Stereocontrol in Supramolecular Photochirogenesis: Photocyclodimerization of 2-Anthracenecarboxylate Mediated by Sulfur-Linked β-Cyclodextrin Dimers
  作者：Jiecheng Ji、Wanhua Wu、Wenting Liang、Guo Cheng、Ryohei Matsushita、Zhiqiang Yan、Xueqin Wei、Ming Rao、De-Qi Yuan、Gaku Fukuhara、Tadashi Mori、Yoshihisa Inoue、Cheng Yang

  DOI：10.1021/jacs.9b01993

  日期：2019.6.12

  tethered dual CD capsule for precisely manipulating the regio- and enantioselectivities of the photocyclodimerization of 2-anthracenecarboxylate (AC) to four stereoisomeric classical 9,10:9',10'-cyclodimers and two nonclassical 5,8:9',10'-cyclodimers. Among the dimeric CD hosts prepared, exo-3-thia-β-CD dimer formed 1:1 and 1:2 host-guest complexes with AC in aqueous solutions, the former of which hindered

  与硫原子或芳烃间隔基连接的立体异构 β-环糊精 (CD) 二聚体旨在创建一个系链双 CD 胶囊，用于精确操纵 2-蒽羧酸 (AC) 光环二聚化为四种立体异构经典 9 的区域和对映选择性， 10:9',10'-环二聚体和两种非经典的 5,8:9',10'-环二聚体。在制备的二聚体 CD 宿主中，exo-3-thia-β-CD 二聚体在水溶液中与 AC 形成 1:1 和 1:2 的主客体复合物，前者阻碍了 AC 的光环二聚化，但后者促进了 AC 与区域的光环二聚化。和对映选择性远高于用天然 β-CD 或其余 β-CD 二聚体获得的选择性。结果证明立体化学结果对连接的糖单元的连接位置和构型和接头长度以及外部变体（例如温度、pH 和添加的盐）高度敏感，因此可通过这些参数进行严格控制。最终，由二聚体 β-CD 宿主介导的 AC 光环二聚化在 0.5°的 pH 5.1 缓冲溶液中以 97-98% 的产率得到对映体纯的
• Switched enantioselectivity by solvent components and temperature in photocyclodimerization of 2-anthracenecarboxylate with 6 A ,6 X -diguanidio− γ -cyclodextrins
  作者：Jigao Yi、Wenting Liang、Xueqin Wei、Jiabin Yao、Zhiqiang Yan、Dan Su、Zhihui Zhong、Guowei Gao、Wanhua Wu、Cheng Yang

  DOI：10.1016/j.cclet.2017.05.004

  日期：2018.1

  -cyclodextrins (CDs) were used as chiral hosts for mediating the enantiodifferentiating [4 + 4] photocyclodimerization of 2-anthracenecarboxylic acid (AC). These γ -CD derivatives form stable 1:2 ternary complexes with AC in aqueous ammonia solutions and the head-to-head photodimers 3 and 4 were greatly enhanced in the presence of these diguanidio- γ -CDs. The enantioselectivity of chiral photodimers 2 and 3 is

  摘要以一系列的6 A，6 X-双胍基-γ-环糊精（CD）为手性基质，介导2-蒽羧酸（AC）的对映体[4 + 4]光环二聚。这些γ-CD衍生物在氨水溶液中与AC形成稳定的1：2三元络合物，并且在这些双胍-γ-CD的存在下，头对头光电二聚体3和4大大增强。手性光二聚体2和3的对映选择性是温度和氨含量的关键函数，通过改变这些外部因素显示出手性反转的产物。