9,9-dimethyl-9H-xanthene-4,5-diamine | 389827-62-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9,9-dimethyl-9H-xanthene-4,5-diamine
• 英文别名: 9,9-Dimethylxanthene-4,5-diamine
• CAS: 389827-62-7
• 化学式: C₁₅H₁₆N₂O
• 分子量: 240.305
• InChiKey: QDTPMBBUUUFNRE-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152 °C
• 沸点：
  417.9±45.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9,9-dimethyl-9H-xanthene-4,5-diamine 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 反应 45.0h， 以52%的产率得到(E)-1,2-bis(5-amino-9,9-dimethyl-9H-xanthen-4-yl)diazene
  参考文献：
  名称：

  Photoinduced Hinge-Like Molecular Motion:  Studies on Xanthene-Based Cyclic Azobenzene Dimers

  摘要：

  Molecular devices incorporating azobenzene units represent active components of smart systems, as they are capable of exhibiting photoregulated cooperative molecular motion. Herein, we describe the synthesis, X-ray crystal analysis, and photochemical and thermal studies of a xanthene based cyclic azobenzene dimer and its precursor. The trans-trans isomer of the azobenzene dimer upon photoirradiation transforms to the cis-cis isomer through an intermediate trans-cis isomer. The X-ray crystal structures of the trans-trans isomer (open) and the cis-cis isomer (closed) provide unambiguous proof for the hinge-like molecular motion in this class of molecules. The inferences drawn from photochemical and thermal studies shed light on the effect of varied substitution and cyclic structures on the different transitions. The lifetime of the cis-cis isomer is estimated to be 6.43 years, whereas the trans-cis isomer is short-lived (2.73 min) at 303 K. A rational explanation for the relative stability of the different isomers is derived from the isokinetic plot and theoretical calculations.

  DOI：

  10.1021/jo0513616
• 作为产物：
  描述：

  benzyl N-[9,9-dimethyl-5-(phenylmethoxycarbonylamino)xanthen-4-yl]carbamate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以53%的产率得到9,9-dimethyl-9H-xanthene-4,5-diamine
  参考文献：
  名称：

  Synthesis of xanthene-derived diimine and iminophosphine compounds as potential chiral bidentate ligands

  摘要：

  The synthesis of one diimine and two iminophosphine chiral ligands bearing a xanthene backbone in, respectively, four and five steps is described. The diimine is characterised by X-ray crystallography. A preliminary test in palladium-catalysed asymmetric allylic alkylation is reported. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01588-x

文献信息

• Novel chiral hydrogen bond donor catalysts based on a 4,5-diaminoxanthene scaffold: application to enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes
  作者：Tetsuhiro Nemoto、Kazumichi Obuchi、Shinji Tamura、Takashi Fukuyama、Yasumasa Hamada

  DOI：10.1016/j.tetlet.2010.12.067

  日期：2011.3

  Novel chiral hydrogen bond donor catalysts based on a 4,5-diamino-9,9′-dimethylxanthene skeleton were designed and synthesized. Among the phenylurea-amide hybrid molecules prepared from various natural/unnatural chiral amino acids, the phenylalanine-derived catalyst, and the proline-derived catalyst were successfully applied to enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes

  设计并合成了一种基于4,5-二氨基-9,9'-二甲基x吨骨架的新型手性氢键供体催化剂。在由各种天然/非天然手性氨基酸制备的苯基脲-酰胺杂化分子中，苯丙氨酸衍生的催化剂和脯氨酸衍生的催化剂成功地用于将1，3-二羰基化合物对硝基烯烃的对映选择性共轭加成。使用2-乙酰基环戊酮和2-甲氧基羰基环戊酮作为前手性亲核试剂，向β-芳基硝基链烯的不对称共轭加成反应具有良好的非对映选择性，从而提供了具有全碳四元立体中心的相应产物，收率高达95％ee。
• Mono- and bimetallic pentacoordinate silicon complexes of a chelating bis(catecholimine) ligand
  作者：Thomas H. Do、Seth N. Brown

  DOI：10.1039/c9dt02475a

  日期：——

  Schiff base condensation of 4,5-diamino-9,9-dimethylxanthene with 4,6-di-tert-butylcatechol-3-carboxaldehyde affords the bis(catecholimine) ligand XbicH4, which can bind metals in both a square bis(catecholate) upper pocket and a pentagonal N2O3 lower pocket. Metalation with PhSiCl3 results in [(XbicH2)SiPh][HCl2], where the silicon adopts a five-coordinate, square pyramidal geometry in the upper pocket

  4,5-二氨基-9,9-二甲基x吨与4,6-二叔丁基邻苯二酚-3-羧酸的席夫碱缩合反应生成双（邻苯二甲酰亚胺）配体XbicH 4，该配体可以结合方形双（邻苯二酚）中的金属）的上口袋和一个五边形的N 2 O 3下口袋。用PhSiCl 3进行金属化会生成[（XbicH 2）SiPh] [HCl 2 ]，其中硅在上腔中采用五坐标方形棱锥几何形状，下腔与亚胺氮上的两个质子结合。LiO t Bu，NaN [SiMe 3 ] 2使亚胺脱质子或AgOAc导致下口袋中的单价金属离子结合，在固态时它采用不寻常的五边形单金字塔形几何形状。该配合物显示出不可逆的电化学，其中氧化在相对较高的电势下发生。
• Xanthene-4,5-diamine derivatives: a study of anion-binding catalysis
  作者：Alison E. Metz、Kailasham Ramalingam、Marisa C. Kozlowski

  DOI：10.1016/j.tetlet.2015.07.058

  日期：2015.9

  This study describes the synthesis of a class of anion-binding catalysts based on a xanthene scaffold. Both unsymmetrical catalysts and C-2-symmetrical catalysts were generated, and were examined in the cyclization of 3- and 2-substituted furans onto N-acyliminium ions. Good conversion for each reaction was observed with a variety of anion-binding catalysts (42-76%). (C) 2015 Elsevier Ltd. All rights reserved.
• New Chiral Bis-Titanium(IV) Catalyst with Dibenzofuran Spacer for Catalytic Asymmetric Allylation of Aldehydes and Aryl Ketones
  作者：Hideo Hanawa、Satoshi Kii、Keiji Maruoka

  DOI：10.1002/1615-4169(20010129)343:1<57::aid-adsc57>3.0.co;2-o

  日期：2001.1.29