9-methyl-9,10-dihydrophenanthren-9-ol | 1226780-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9-methyl-9,10-dihydrophenanthren-9-ol
• 英文别名: 9-methyl-10H-phenanthren-9-ol
• CAS: 1226780-46-6
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: GESZWCQVHMAMPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(2-bromophenyl)-2-phenylpropan-2-ol 在 palladium diacetate 、 potassium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以52%的产率得到9-methyl-9,10-dihydrophenanthren-9-ol
  参考文献：
  名称：

  Manganese Catalysts for C−H Activation: An Experimental/Theoretical Study Identifies the Stereoelectronic Factor That Controls the Switch between Hydroxylation and Desaturation Pathways

  摘要：

  We describe competitive C-H bond activation chemistry of two types, desaturation and hydroxylation, using synthetic manganese catalysts with several substrates. 9,10-Dihydrophenanthrene (DHP) gives the highest desaturation activity, the final products being phenanthrene (P1) and phenanthrene 9,10-oxide (P3), the latter being thought to arise from epoxidation of some of the phenanthrene. The hydroxylase pathway also occurs as suggested by the presence of the dione product, phenanthrene-9,10-dione (P2), thought to arise from further oxidation of hydroxylation intermediate 9-hydroxy-9,10-dihydrophenanthrene. The experimental work together with the density functional theory (DFT) calculations shows that the postulated Mn oxo active species, [Mn(O)(tpp)(Cl)] (tpp = tetraphenylporphyrin), can promote the oxidation of dihydrophenanthrene by either desaturation or hydroxylation pathways. The calculations show that these two competing reactions have a common initial step, radical H abstraction from one of the DHP sp(3) C-H bonds. The resulting Mn hydroxo intermediate is capable of promoting not only OH rebound (hydroxylation) but also a second H abstraction adjacent to the first (desaturation). Like the active Mn-V=O species, this Mn-IV-OH species also has radical character on oxygen and can thus give H abstraction. Both steps have very low and therefore very similar energy barriers, leading to a product mixture. Since the radical character of the catalyst is located on the oxygen p orbital perpendicular to the Mn-IV-OH plane, the orientation of the organic radical with respect to this plane determines which reaction, desaturation or hydroxylation, will occur. Stereoelectronic factors such as the rotational orientation of the OH group in the enzyme active site are thus likely to constitute the switch between hydroxylase and desaturase behavior.

  DOI：

  10.1021/ja908744w

文献信息

• METHODS FOR PREPARING POLYMERIC REAGENTS
  申请人：Nektar Therapeutics

  公开号：US20150141665A1

  公开（公告）日：2015-05-21

  The present invention provides among other things methods for preparing polymeric reagents, wherein the method comprises (a) providing an aromatic moiety bearing a hydroxy group, a first amino group and a second amino group; (b) reacting a functional group reagent with the hydroxy group to result in a hydroxy group bearing a functional group capable of reacting with an amino group of an active agent and resulting in a hydolyzable carbamate; and (c) reacting a plurality of poly(alkylene glycol) water-soluble polymers bearing a reactive group with the first amino group and second amino group to result in (i) a first amino group bearing a water-soluble polymer through a spacer moiety, and (ii) a second amino group bearing a second water-soluble polymer through a spacer moiety.

  本发明提供了制备聚合试剂的方法，其中该方法包括（a）提供一种带有羟基、第一氨基和第二氨基的芳香基团；（b）将功能性试剂与羟基反应，以得到带有功能性基团的羟基，该功能性基团能够与活性剂的氨基反应，并产生可水解的碳酸酯；以及（c）将带有反应性基团的多种聚（烷基乙二醇）水溶性聚合物与第一氨基和第二氨基反应，以得到（i）通过间隔基团带有第一氨基的水溶性聚合物，以及（ii）通过间隔基团带有第二氨基的第二种水溶性聚合物。
• Methods for Preparing Polymeric Reagents
  申请人：Nektar Therapeutics

  公开号：US20140107349A1

  公开（公告）日：2014-04-17

  The present invention provides among other things methods for preparing polymeric reagents, wherein the method comprises (a) providing an aromatic moiety bearing a hydroxy group, a first amino group and a second amino group; (b) reacting a functional group reagent with the hydroxy group to result in a hydroxy group bearing a functional group capable of reacting with an amino group of an active agent and resulting in a hydrolyzable carbamate; and (c) reacting a plurality of poly(alkylene glycol) water-soluble polymers bearing a reactive group with the first amino group and second amino group to result in (i) a first amino group bearing a water-soluble polymer through a spacer moiety, and (ii) a second amino group bearing a second water-soluble polymer through a spacer moiety.

  本发明提供了制备聚合试剂的方法，其中该方法包括(a)提供一种带有羟基、第一氨基和第二氨基的芳香基团；(b)将功能性试剂与羟基反应，得到带有能够与活性试剂的氨基基团反应并生成可水解的氨基甲酸酯的官能基的羟基基团；(c)将带有反应基团的多种聚(烷氧基乙烯醇)水溶性聚合物与第一氨基和第二氨基反应，得到(i)通过间隔基团带有第一氨基的水溶性聚合物，以及(ii)通过间隔基团带有第二氨基的第二种水溶性聚合物。
• Copper-Catalyzed Intramolecular Aldehyde–Ketone Nucleophilic Additions for the Synthesis of Chromans Bearing a Tertiary Alcohol Motif
  作者：Chenghao Zhu、Wenbo Jiang、Da Ma

  DOI：10.1021/acs.joc.3c02365

  日期：2024.1.19

  The synthesis of chroman-3-ol derivatives via intramolecular nucleophilic additions has been established. Aldehydes can be used as alkyl carbanion equivalents via reductive polarity reversal which is facilitated by a copper catalyst and N-heterocyclic carbene ligand under mild conditions. The key to success is the difference in reaction activity between aldehydes and ketones. Finally, this methodology

  已经建立了通过分子内亲核加成合成色满-3-醇衍生物的方法。通过铜催化剂和 N-杂环卡宾配体在温和条件下促进还原极性反转，醛可用作烷基碳负离子等价物。成功的关键是醛和酮之间反应活性的差异。最后，该方法还可用于构建含有叔醇的其他环状结构，包括四氢化萘、环己烷、茚满和9,10-二氢菲。
• COMPOSITION COMPRISING A POLYMERIC REAGENT
  申请人：Nektar Therapeutics

  公开号：US20160324973A1

  公开（公告）日：2016-11-10

  The present invention provides among other things a composition of a polymeric reagent and an antioxidant, such as butylated hydroxyl toluene.
• US8435505B2
  申请人：——

  公开号：US8435505B2

  公开（公告）日：2013-05-07