1-methoxyperylene

• 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: 1-methoxyperylene
• 英文别名: methyl-perylen-1-yl ether；Methyl-perylen-1-yl-aether；1-Methoxy-perylen
• 化学式: C₂₁H₁₄O
• 分子量: 282.342
• InChiKey: BGWWAQNFYNFVKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯基氯化膦 、 (+/-)-8-bromo-2'-methoxy-1,1'-binaphthyl 在 1,2-双(二苯基膦)乙烷氯化镍 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以32%的产率得到(S)-(+)-8-diphenylphosphino-2'-methoxy-1,1'-binaphthyl
  参考文献：
  名称：

  2,8′-Disubstituted-1,1′-Binaphthyls: A New Pattern in Chiral Ligands

  摘要：

  The title binaphthyls 19 and 26, which are the positional isomers of 2-methoxy-2'-(diphenylphosphino)-1,1'-binaphthyl (MOP, 19) and 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN, 26), have been synthesized by Suzuki coupling as the key step (10 + 15 --> 18), followed by functional group transformations, involving C-P and C-N bond formation (18 --> 19 and 18 --> 23). Racemic intermediate 22 was resolved by co-crystallization with N-benzylcinchonidinium chloride and the absolute configuration determined by X-ray crystallography. These novel binaphthyls are configurationally stable and, as such, potentially usable as chiral ligands in asymmetric reactions. Michael addition of the glycine-derived enolate 40 to methyl acrylate, carried out in the presence of (R)-(-)-27 as the chiral phase-transfer catalyst, afforded L-glutamic acid (S)-(+)-43 of 92% ee (after hydrolysis of the primary product).

  DOI：

  10.1002/1521-3765(20021018)8:20<4633::aid-chem4633>3.0.co;2-n

文献信息

• Method of Quenching Electronic Excitation of Chromophore-Containing Organic Molecules in Photoactive Compositions
  申请人：HallStar Innovations Corp.

  公开号：EP2025323A1

  公开（公告）日：2009-02-18

  The photostabilizing electronic excited state energy - particularly single state energy from a UV-absorbing molecule has been found to be readily transferred to (accepted by) α-cyanodiphenylacrylate compounds of formulas (I) and (V) having an alkoxy radical preferably in the four (para) position (hereinafter methoxy crylenes) on one or both of the phenyl rings: wherein at least one of R1 and R2 is a straight or branched chain C1-C12 alkoxy radical, preferably C1-C8, more preferably C1-C4, and most preferably methoxy, and any non-alkoxy radical R1 or R2 is hydrogen; and R3 is a straight or branched chain C1-C24 alkyl radical, preferably C12-C24, more preferably C20; wherein A and B are the same or different and are selected from the group consisting of oxygen, amino and sulfur; R1 and R3 are the same or different and are selected from the group consisting of C1-C30 alkyl, C2-C30 alkylene, C2-C30 alkyne, C3-C8 cycloalkyl, C1-C30 substituted alkylene, C2-C30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R2 is selected from the group consisting of C1-C30 alkyl, C2-C30 alkylene, C2C30 alkyne, C3-C8 cycloalkyl, C1-C30 substituted alkyl, C3-C8 substituted cycloalkyl, C1-C30 substituted alkylene, C2-C30 substituted alkyne; R4, R5, R6 and R7 are the same or different and are selected from the group consisting of C1-C30 alkoxy straight chin on branched and a, b, c and d are each either 0 or 1, and a, b, c and d add up to 1, 2, 3, or 4.

  研究发现，来自紫外线吸收分子的光稳定电子激发态能量（尤其是单态能量）很容易转移到（被）α-氰基二苯丙烯酸酯化合物上，这些化合物的式子（I）和（V）在一个或两个苯基环上最好有一个位于四（对位）的烷氧基（以下简称甲氧基冰晶石）： 其中 R1 和 R2 中至少有一个是直链或支链 C1-C12 烷氧基，优选 C1-C8，更优选 C1-C4，最优选甲氧基，任何非烷氧基基 R1 或 R2 均为氢；R3 是直链或支链 C1-C24 烷基，优选 C12-C24，更优选 C20； 其中 A 和 B 相同或不同，且选自由氧、氨基和硫组成的组；R1 和 R3 相同或不同，且选自由 C1-C30 烷基、C2-C30 亚烷基、C2-C30 烷基、C3-C8 环烷基、C1-C30 取代亚烷基、C2-C30 取代烷基、芳基、取代芳基、杂芳基、杂环烷基、取代杂芳基和取代杂环烷基组成的组；R2选自由C1-C30烷基、C2-C30亚烷基、C2C30炔基、C3-C8环烷基、C1-C30取代烷基、C3-C8取代环烷基、C1-C30取代亚烷基、C2-C30取代炔基组成的组；R4、R5、R6和R7相同或不同，选自由C1-C30直链烷氧基和支链烷氧基组成的组，a、b、c和d各自为0或1，且a、b、c和d相加为1、2、3或4。
• US5100762A
  申请人：——

  公开号：US5100762A

  公开（公告）日：1992-03-31
• 2,8′-Disubstituted-1,1′-Binaphthyls: A New Pattern in Chiral Ligands
  作者：Štěpán Vyskočil、Luděk Meca、Iva Tišlerová、Ivana Císařová、Miroslav Polášek、Syuzanna R. Harutyunyan、Yuri N. Belokon、Russel M. J. Stead、Louis Farrugia、Stephen C. Lockhart、William L. Mitchell、Pavel Kočovský

  DOI：10.1002/1521-3765(20021018)8:20<4633::aid-chem4633>3.0.co;2-n

  日期：2002.10.18

  The title binaphthyls 19 and 26, which are the positional isomers of 2-methoxy-2'-(diphenylphosphino)-1,1'-binaphthyl (MOP, 19) and 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN, 26), have been synthesized by Suzuki coupling as the key step (10 + 15 --> 18), followed by functional group transformations, involving C-P and C-N bond formation (18 --> 19 and 18 --> 23). Racemic intermediate 22 was resolved by co-crystallization with N-benzylcinchonidinium chloride and the absolute configuration determined by X-ray crystallography. These novel binaphthyls are configurationally stable and, as such, potentially usable as chiral ligands in asymmetric reactions. Michael addition of the glycine-derived enolate 40 to methyl acrylate, carried out in the presence of (R)-(-)-27 as the chiral phase-transfer catalyst, afforded L-glutamic acid (S)-(+)-43 of 92% ee (after hydrolysis of the primary product).