(S)-(anthracen-9-ylmethyl)-α-phenylethylamine | 852806-99-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (S)-(anthracen-9-ylmethyl)-α-phenylethylamine
• 英文别名: N-(anthracen-9-ylmethyl)-1-phenylethanamine；(1S)-N-(anthracen-9-ylmethyl)-1-phenylethanamine
• CAS: 852806-99-6
• 化学式: C₂₃H₂₁N
• 分子量: 311.426
• InChiKey: MXKGRQXMBHRQMW-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-氯丙酰氯 、 (S)-(anthracen-9-ylmethyl)-α-phenylethylamine 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以70%的产率得到N-(anthracen-9-ylmethyl)-3-chloro-N-(1-phenylethyl)propanamide
  参考文献：
  名称：

  基于1-乙烯基咪唑的高分子化学传感器的合成与性能

  摘要：

  通过聚（1-乙烯基咪唑）（PVI）（Mw ~ 63000）通过含有蒽荧光团的烷基化化合物季铵化合成对阳离子和阴离子具有化学传感器特性的聚（1-乙烯基咪唑氯化物）衍生物。聚({3-[2-(anthracen-9-ylmethyl)amino]ethyl}-1-vinylimidazolium chloride) 表现出选择性，在 Zn 阳离子存在下，相对荧光强度 I/I0 增加了 20 倍以上。聚（{3-[2-（蒽-9-基甲基）（3,5-二氯苯基）氨基]-2-氧乙基}-1-乙烯基咪唑氯化物）作为 AcO 的化学传感器，改变其 DMSO 溶液的颜色淡黄色至亮橙色。

  DOI：

  10.24820/ark.5550190.p010.625
• 作为产物：
  描述：

  (S)-9-(anthracen-9-ylmethylene)-α-phenylethylamine 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-(anthracen-9-ylmethyl)-α-phenylethylamine
  参考文献：
  名称：

  Chemoselective and enantioselective fluorescent recognition of sugar alcohols by a bisboronic acid receptor

  摘要：

  双硼酸 3 与六碳糖醇的结合力强且具有对映选择性，但与五碳或四碳糖醇或单糖的结合力不强。

  DOI：

  10.1039/b501249j

文献信息

• Chemoselective and enantioselective fluorescent recognition of sugar alcohols by a bisboronic acid receptor
  作者：Jianzhang Zhao、Tony D. James

  DOI：10.1039/b501249j

  日期：——

  Bisboronic acid 3 binds strongly and enantioselectively with six-carbon sugar alcohols but does not bind strongly with five- or four-carbon sugar alcohols or monosaccharides.

  双硼酸 3 与六碳糖醇的结合力强且具有对映选择性，但与五碳或四碳糖醇或单糖的结合力不强。
• Synthesis and dynamics of atropisomeric (S)-N-(α-phenylethyl)benzamides
  作者：Gabriela Huelgas、Sylvain Bernès、Mario Sánchez、Leticia Quintero、Eusebio Juaristi、Cecilia Anaya de Parrodi、Patrick J. Walsh

  DOI：10.1016/j.tet.2007.10.010

  日期：2007.12

  The synthesis of atropisomeric 2-substituted benzamides 2a-e, 3a-e, and 4a-e, and characterization by X-ray structure analysis of 2d, 2e, 3c, 3e, 4c, and 4e are reported. Dynamic H-1 NMR spectroscopic studies of benzamides 2b-d, 3b-d, and 4b-d indicate that only two of the four possible rotamers are present in solution, with population ratios ranging between 1.5:1 and 4. 1:1. The measured free energy of activation to interconversion of the rotamers ranged from 12.4 to 18.9 kcal mol(-1). Benzamides ArCON[(S)-phenethyl]2 (2e, 3e, and 4e), exhibited atropisomer ratios between 1.7:1 and 1: 1, and free energies of interconversion of the rotamers ranged from 11.5 to 17.6 kcal mol(-1). The highest rotation barriers were observed for the ortho-nitro derivatives 2a-e. Molecular calculations at the semiempirical level (PM3MM) gave free energies of activation for benzamides 2e and 3e of 23.6 and 12.4 kcal mol(-1), respectively, which are comparable to the experimental values. (c) 2007 Elsevier Ltd. All rights reserved.
• An Enantioselective Fluorescent Sensor for Sugar Acids
  作者：Jianzhang Zhao、Matthew G. Davidson、Mary F. Mahon、Gabriele Kociok-Köhn、Tony D. James

  DOI：10.1021/ja046289s

  日期：2004.12.1

  Chiral fluorescent boronic acid 1 was found to be a highly enantioselective, chemoselective, and sensitive sensor for sugar acids, such as tartaric acid. Enantioselectivities (K-R/K-S) of up to 550:1, chemoselectivity up to 11000:1, and sensitivities in the micromolar range with sensor 1 were observed. Single-crystal X-ray analysis was used to confirm the structure of the fluorescent species.
• Synthesis and properties of polymer chemosensors based on 1-vinylimidazole
  作者：Vladimir A. Bren、Ivan E. Tolpygin、Yurii V. Revinskii、Karina S. Tikhomirova、Alexander D. Dubonosov、Vladimir I. Minkin

  DOI：10.24820/ark.5550190.p010.625

  日期：——

  Derivatives of poly(1-vinylimidazolium chloride) possessing chemosensor properties to cations and anions were synthesized by quaternization of poly-(1-vinylimidazole) (PVI) (Mw ~ 63000) by alkylating compounds containing anthracene fluorophore. Poly(3-[2-(anthracen-9-ylmethyl)amino]ethyl}-1-vinylimidazolium chloride) demonstrates selectivity with more than a 20 fold increase in relative fluorescence

  通过聚（1-乙烯基咪唑）（PVI）（Mw ~ 63000）通过含有蒽荧光团的烷基化化合物季铵化合成对阳离子和阴离子具有化学传感器特性的聚（1-乙烯基咪唑氯化物）衍生物。聚(3-[2-(anthracen-9-ylmethyl)amino]ethyl}-1-vinylimidazolium chloride) 表现出选择性，在 Zn 阳离子存在下，相对荧光强度 I/I0 增加了 20 倍以上。聚（3-[2-（蒽-9-基甲基）（3,5-二氯苯基）氨基]-2-氧乙基}-1-乙烯基咪唑氯化物）作为 AcO 的化学传感器，改变其 DMSO 溶液的颜色淡黄色至亮橙色。