1-Methylamino(9H,10)anthraceneone | 915955-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-Methylamino(9H,10)anthraceneone
• 英文别名: 1-methylamino-10H-anthracen-9-one；4-(methylamino)-10H-anthracen-9-one
• CAS: 915955-90-7
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: HLRDFQLSONFWHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-己基-1H-吡咯-2,5-二酮 、 1-Methylamino(9H,10)anthraceneone 在 (2S,6s)-2,6-二苄基-2,3,5,6-四氢-1H-咪唑并[1,2-a]咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 2-hexyl-4-hydroxy-8-methylamino-3a,4,9,9a-tetrahydro-4,9[1,2]benzeno-1H-benz[f]isoindole-1,3(2H)-dione 、 2-hexyl-4-hydroxy-8-methylamino-3a,4,9,9a-tetrahydro-4,9[1,2]benzeno-1H-benz[f]isoindole-1,3(2H)-dione
  参考文献：
  名称：

  手性双环胍催化蒽酮的对映选择性反应

  摘要：

  手性双环胍 1 被发现是蒽酮和各种亲二烯体之间反应的极好催化剂。该催化剂可以耐受一系列取代基和取代模式，使几种蒽酮衍生物适用于该反应。Diels-Alder 和 Michael 加合物均以优异的产率、高区域选择性和高对映选择性获得。这是高度对映选择性碱催化蒽酮 Diels-Alder 反应的第一个案例。

  DOI：

  10.1021/ja064636n
• 作为产物：
  描述：

  分散红9 生成 1-Methylamino(9H,10)anthraceneone
  参考文献：
  名称：

  Baughman George L., Weber Eric J., Environ. Sci. and Technol., 28 (1994) N 2, S 267-276

  摘要：

  DOI：

文献信息

• Transformation of dyes and related compounds in anoxic sediment: kinetics and products
  作者：George L. Baughman、Eric J. Weber

  DOI：10.1021/es00051a013

  日期：1994.2.1

  The reactions of several azo, anthraquinone, and quinoline dyes were studied in settled sediments. Several 1-substituted anthraquinones were lost from sediment with half-lives less than 10 days. For monosubstituted 1-amino and 1-methylamino (Disperse Red 9) compounds, the most stable product is the intramolecularly hydrogen-bonded anthrone. The 1,4-diaminoanthraquinone (Disperse Violet 1) and 1,4-diamino-2-methoxyanthraquinone (Disperse Red 11) were lost without formation of detectable products except for a demethylation product of the latter. Both the anthrone from Disperse Red 9 and the demethylation product of Disperse Red 11 reacted with half-lives of a few months, but other major products were not detected. An azo dye (Solvent Red 1) and a quinoline dye (Solvent Yellow 33) were transformed with half-lives of a few days and months, respectively. The azo dye reacted by reductive cleavage of the azo bond.
• Baughman George L., Weber Eric J., Environ. Sci. and Technol., 28 (1994) N 2, S 267-276
  作者：Baughman George L., Weber Eric J.

  DOI：——

  日期：——
• Chiral Bicyclic Guanidine-Catalyzed Enantioselective Reactions of Anthrones
  作者：Juan Shen、Thanh Truc Nguyen、Yong-Peng Goh、Weiping Ye、Xiao Fu、Junye Xu、Choon-Hong Tan

  DOI：10.1021/ja064636n

  日期：2006.10.1

  catalyst for reactions between anthrones and various dienophiles. The catalyst can tolerate a range of substituents and substitution patterns, making several anthrone derivatives suitable for this reaction. Both Diels-Alder and Michael adducts were obtained in excellent yields, high regioselectivities, and high enantioselectivities. This is the first case of a highly enantioselective base-catalyzed anthrone

  手性双环胍 1 被发现是蒽酮和各种亲二烯体之间反应的极好催化剂。该催化剂可以耐受一系列取代基和取代模式，使几种蒽酮衍生物适用于该反应。Diels-Alder 和 Michael 加合物均以优异的产率、高区域选择性和高对映选择性获得。这是高度对映选择性碱催化蒽酮 Diels-Alder 反应的第一个案例。