(6aR,6bS,12bS,12cR)-3,10-Dimethoxy-6a,6b,12b,12c-tetrahydro-5,8-dioxa-dibenzo[a,i]biphenylene-6,7-dione | 37818-63-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: (6aR,6bS,12bS,12cR)-3,10-Dimethoxy-6a,6b,12b,12c-tetrahydro-5,8-dioxa-dibenzo[a,i]biphenylene-6,7-dione
• 英文别名: (1R,2S,11S,12R)-6,17-dimethoxy-9,14-dioxapentacyclo[10.8.0.02,11.03,8.015,20]icosa-3(8),4,6,15(20),16,18-hexaene-10,13-dione
• CAS: 37818-63-6
• 化学式: C₂₀H₁₆O₆
• 分子量: 352.343
• InChiKey: RXGCYAPVIBVWST-USTZCAOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7-甲氧基香豆素 在 钯 作用下， 以 重水 为溶剂， 反应 10.0h， 以7%的产率得到(6aR,6bS,12bS,12cR)-3,10-Dimethoxy-6a,6b,12b,12c-tetrahydro-5,8-dioxa-dibenzo[a,i]biphenylene-6,7-dione
  参考文献：
  名称：

  水溶性纳米反应容器中香豆素的光二聚化模板化

  摘要：

  八面体钯纳米笼用作控制容器中香豆素光二聚化的反应容器。在这项研究中探索的香豆素衍生物在Pd纳米笼中发生反应，选择性地产生了一个syn head - head二聚体，而在水中，它们要么生成二聚体的混合物，要么生成不同的异构体。选择性二聚化被解释为意味着单体通过弱的分子间作用力被笼子预组织。与先前用于控制光二聚化反应的几何结构的其他宿主相比，在纳米笼中获得的选择性更为通用和可预测。

  DOI：

  10.1021/jo0606498

文献信息

• Manipulating Photochemical Reactivity of Coumarins within Cucurbituril Nanocavities
  作者：Nilotpal Barooah、Barry C. Pemberton、J. Sivaguru

  DOI：10.1021/ol801256r

  日期：2008.8.7

  Coumarin derivatives that are either cationic (7-ammonium) or neutral (7-hydroxy, 7-methoxy, 6-methyl) form a 1:2 host-guest complex with cucurbit[8]uril (CB[8]). Direct irradiation of these coumarin@CB[8] complexes in water gives head-to-tail (HT) adduct as the major product. The nature of the functional group (polar or nonpolar) at the 6 or 7 position on the coumarin dictates the type of HT adduct

  阳离子（7-铵）或中性（7-羟基，7-甲氧基，6-甲基）香豆素衍生物与葫芦[8]尿嘧啶（CB [8]）形成1：2主体-客体复合物。这些香豆素@CB [8]络合物在水中的直接辐照产生头对尾（HT）加合物作为主要产物。香豆素在6或7位上的官能团（极性或非极性）的性质决定了HT加合物的类型（顺式或反式）。据推测，可用的自由体积和疏水的封闭环境是所观察到的选择性的原因。
• Stereospecific photodimerization of coumarins in crystalline inclusion complexes. Molecular and crystal structure of 1:2 complex of (S,S)-(-)-1,6-bis(o-chlorophenyl)-1,6-diphenyl-hexa-2,4-diyne-1,6-diol and coumarin
  作者：J. Narasimha Moorthy、K. Venkatesan

  DOI：10.1021/jo00024a052

  日期：1991.11
• Photodimerization of coumarins in solid cyclodextrin inclusion complexes
  作者：J. Narasimha Moorthy、K. Venkatesan、Richard G. Weiss

  DOI：10.1021/jo00038a012

  日期：1992.6

  The photodimerizations of coumarin and eight of its derivatives are found to proceed selectively in solid inclusion complexes with beta- and gamma-cyclodextrins (beta- and gamma-CD). The distribution of photodimers from these complexes is compared with those from the neat coumarin solids and their solutions in a variety of solvents. By assuming that the stereochemistry of the dimers reflects the packing arrangements of their precursors in the CD complexes, several hypotheses concering the locations and arrangements of the coumarins in the host toruses have been made. The stoichiometries of the complexes have been assigned on the basis of the presence or absence of photodimers and from NMR integration ratios of characteristic coumarin and saccharide protons. The relative orientations of substituted coumarins within a complex are inferred from the stereochemistry of the photodimers. Depending upon the substitution pattern of the coumarin molecules and the type of CD employed, complexes whose guest-host stoichiometries are 1:1, 2:1, and 2:2 have been identified. In several instances, dimers not available from irradiation of neat solid coumarins or their solutions have been obtained from the CD complexes.
• Templating Photodimerization of Coumarins within a Water-Soluble Nano Reaction Vessel
  作者：S. Karthikeyan、V. Ramamurthy

  DOI：10.1021/jo0606498

  日期：2006.8.1

  An octahedral Pd nanocage serves as a reaction vessel to control photodimerization of coumarins in water. The coumarin derivatives explored in this study react within the Pd nanocage to selectively yield a syn head−head dimer, whereas in water, they yield either a mixture of dimers or a different isomer. The selective dimerization is interpreted to mean that the monomers are preorganized by the cage

  八面体钯纳米笼用作控制容器中香豆素光二聚化的反应容器。在这项研究中探索的香豆素衍生物在Pd纳米笼中发生反应，选择性地产生了一个syn head - head二聚体，而在水中，它们要么生成二聚体的混合物，要么生成不同的异构体。选择性二聚化被解释为意味着单体通过弱的分子间作用力被笼子预组织。与先前用于控制光二聚化反应的几何结构的其他宿主相比，在纳米笼中获得的选择性更为通用和可预测。