(+)-(R)-1-Anthracen-9-ylethanol | 94942-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (+)-(R)-1-Anthracen-9-ylethanol
• 英文别名: α-methyl-9-anthracenemethanol；R-(+)-α-(9-anthryl)ethanol；(R)-1-(anthracen-9-yl)ethan-1-ol；(R)-1-(anthracen-9-yl)ethanol；1-(anthracen-9-yl)ethan-1-ol；(R)-1-anthracen-9-ylethanol；(1R)-1-anthracen-9-ylethanol
• CAS: 94942-50-4
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: WRADANNQOTZBDC-LLVKDONJSA-N

物化性质

• 熔点：
  112-114 °C(Solv: ligroine (8032-32-4); dichloromethane (75-09-2))
• 沸点：
  417.3±14.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-(R)-1-Anthracen-9-ylethanol 生成
  参考文献：
  名称：

  分子内T 2致敏的不对称诱导：α-（9″-蒽基）乙基螺[环丙烷-1,9'-芴] -2-羧酸酯的光异构化

  摘要：

  α-（9″-蒽）乙基螺[环丙烷-1,9'-芴] -2-羧酸酯（1c⇄2c）的光异构化是通过选择性的分子内能量从第二个三重态蒽基转移到非对映异构体进行的。芴基部分。利用光学活性α-（9″-蒽基）乙基的不对称诱导以高光学和化学产率实现。

  DOI：

  10.1016/s0040-4039(01)80368-3
• 作为产物：
  描述：

  9-乙酰基蒽 在 N,N-diethylaniline borane 、 硼酸三甲酯 、 chiral 2-(diphenylhydroxymethyl)pyrrolidine 作用下， 以 甲苯 为溶剂， 生成 (+)-(R)-1-Anthracen-9-ylethanol
  参考文献：
  名称：

  Stereochemical Sensitivity of the Human UDP-glucuronosyltransferases 2B7 and 2B17

  摘要：

  A set of 28 enantiomers comprising rigid and flexible secondary alcohols was synthesized by the asymmetric Corey-Bakshi-Shibata reduction. The enantiomerically pure alcohols were subjected to enzymatic glucuronidation assays employing the human UDP-glucuronosyltransferases (UGTs) 2B7 and 2BI7. Both UGTs displayed high levels of stereo selectivity, favoring the conjugation of the (R)-enantiomers over their respective (S)-stereoisomers at eudismic ratios up to 256. The spatial arrangement of the hydroxy group determined the diastereoselectivity of the UGT2B17-catalyzed reaction in agreement with Pfeiffer's rule (eudismic activity quotient = 0.83 +/- 0.14). Inhibition studies revealed that the enantiomers had similar affinities toward the enzymes. The diastereoselectivity of the UGT-catalyzed conjugation stemmed, therefore, from the arrangement of the substrates in the catalytic site, rather than from distinct affinities toward the enzymes. Taken together, this study showed that metabolic enzymes that are generally conceived to be rather "flexible" in nature are capable of displaying high levels of chiral distinction.

  DOI：

  10.1021/jm051142c

文献信息

• Solution-phase synthesis and evaluation of tetraproline chiral stationary phases
  作者：Zhi Dai、Guozhong Ye、Charles U. Pittman、Tingyu Li

  DOI：10.1002/chir.22001

  日期：2012.4

  solution‐phase synthesis of multigram amounts of two 9‐fluorenylmethoxycarbonyl (Fmoc)‐protected tetraproline peptides. These tetraproline peptides were then attached to amino derivatized silica gel. The replacement of the Fmoc group with the trimethylacetyl group lead to two tetraproline chiral stationary phases (CSPs). A comparison of the chromatographic behavior of these two solution‐phase‐synthesized

  开发了一种协议方案，用于溶液相合成多克数量的两个9-芴基甲氧基羰基（Fmoc）保护的四脯氨酸肽。然后将这些四脯氨酸肽连接到氨基衍生的硅胶上。用三甲基乙酰基取代Fmoc基团会导致两个四脯氨酸手性固定相（CSP）。将这两种溶液相合成的四脯氨酸CSP与通过逐步固相合成制备的CSP的色谱行为进行比较，结果表明，这三种溶液均具有相似的色谱性能，可分离53种模型分析物。这表明寡聚脯氨酸的溶液相合成具有良好的批次重现性，选择器均质性以及可能的低成本等特定优势，是寡聚脯氨酸CSP固相合成的可行替代方法。手性，2012年。©2012 Wiley Periodicals，Inc.。
• <b>PQXdpap</b>: Helical Poly(quinoxaline-2,3-diyl)s Bearing 4-(Dipropylamino)pyridin-3-yl Pendants as Chirality-Switchable Nucleophilic Catalysts for the Kinetic Resolution of Secondary Alcohols
  作者：Takeshi Yamamoto、Ryo Murakami、Michinori Suginome

  DOI：10.1021/acs.orglett.1c03134

  日期：2021.11.19

  Helically chiral poly(quinoxaline-2,3-diyl)s bearing 4-(dipropylamino)pyridin-3-yl pendants at the 5-position of the quinoxaline ring (PQXdpap) exhibited high catalytic activities and moderate to high selectivities (up to s = 87) in the acylative kinetic resolution of secondary alcohols. The solvent-dependent helical chirality switching of PQXdpap between pure toluene and a 1:1 mixture of toluene and

  在喹喔啉环 ( PQXdpap )的 5 位带有 4-(二丙氨基) 吡啶-3-基侧链的螺旋手性聚 (quinoxaline-2,3-diyl)s表现出高催化活性和中到高选择性（高达s = 87) 在仲醇的酰化动力学拆分中。PQXdpap在纯甲苯和 1:1 的甲苯和 1,1,2-三氯乙烷混合物之间的溶剂依赖性螺旋手性转换能够从单一催化剂。
• Development of New HPLC Chiral Stationary Phases Based on Native and Derivatized Cyclofructans
  作者：Ping Sun、Chunlei Wang、Zachary S. Breitbach、Ying Zhang、Daniel W. Armstrong

  DOI：10.1021/ac902257a

  日期：2009.12.15

  An unusual class of chiral selectors, cyclofructans, is introduced for the first time as bonded chiral stationary phases. Compared to native cyclofructans (CFs), which have rather limited capabilities as chiral selectors, aliphatic- and aromatic-functionalized CF6s possess unique and very different enantiomeric selectivities. Indeed, they are shown to separate a very broad range of racemic compounds. In particular, aliphatic-derivatized CF6s with a low substitution degree baseline separate all tested chiral primary amines. It appears that partial derivatization on the CF6 molecule disrupts the molecular internal hydrogen bonding, thereby making the core of the molecule more accessible. In contrast, highly aromatic-functionalized CF6 stationary phases lose most of the enantioselective capabilities toward primary amines, however they gain broad selectivity for most other types of analytes. This class of stationary phases also demonstrates high “loadability” and therefore has great potential for preparative separations. The variations in enantiomeric selectivity often can be correlated with distinct structural features of the selector. The separations occur predominantly in the presence of organic solvents.

  首次引入一类不寻常的手性选择剂——环糊精作为键合型手性固定相。与天然环糊精（CFs）相比，其作为手性选择剂的能力相当有限，而脂族和芳族功能化的CF6具有独特且截然不同的对映体选择性。事实上，它们能够分离非常广泛的消旋化合物。特别是，低取代度的脂族衍生化CF6能够基线分离所有测试的手性伯胺。似乎部分衍生化作用于CF6分子会破坏分子内部的氢键，从而使分子核心更易接近。相比之下，高度芳族功能化的CF6固定相在伯胺的对映选择能力方面丧失了大部分能力，但它们对大多数其他类型的分析物获得了广泛的选择性。这类固定相还表现出高“负荷能力”，因此具有在制备分离方面的巨大潜力。对映体选择性的变化通常可以与选择剂的独特结构特征相关联。分离主要在有机溶剂存在下发生。
• Acylative Kinetic Resolution of Alcohols Using a Recyclable Polymer-Supported Isothiourea Catalyst in Batch and Flow
  作者：Rifahath Mon Neyyappadath、Ross Chisholm、Mark D. Greenhalgh、Carles Rodríguez-Escrich、Miquel A. Pericàs、Georg Hähner、Andrew D. Smith

  DOI：10.1021/acscatal.7b04001

  日期：2018.2.2

  prepared and used for the acylative kinetic resolution of secondary alcohols. A wide range of alcohols, including benzylic, allylic, and propargylic alcohols, cycloalkanol derivatives, and a 1,2-diol, has been resolved using either propionic or isobutyric anhydride with good to excellent selectivity factors obtained (28 examples, s values up to 600). The catalyst can be recovered and reused by a simple filtration

  已经制备了基于均相催化剂HyperBTM的聚苯乙烯负载的异硫脲催化剂，并将其用于仲醇的酰基动力学拆分。宽范围的醇，包括苄基，烯丙基，和炔丙基醇，环烷醇衍生物，和1,2-二醇的，已使用或者丙酸或异丁酸酐以良好到获得优异的选择性因子（28个实施例中，解决了小号值最大为600）。催化剂可以通过简单的过滤和洗涤程序进行回收和再利用，而无需采取特殊的预防措施。证明了该催化剂的可回收性（15个循环），活性或选择性均无明显损失。可循环使用的催化剂还用于使用不同的酸酐顺序拆分10种不同的醇，各循环之间无交叉污染。最后，在连续流工艺中的成功应用证明了用于流态醇动力学分离的固定化Lewis碱催化剂的第一个实例。
• Kinetic Resolution of Secondary Carbinols by a Chiral<i>N</i>,<i>N</i>-4-Dimethylaminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Hydrogen Bonding Affects Catalytic Activity and Enantioselectivity
  作者：Kazuki Fujii、Koichi Mitsudo、Hiroki Mandai、Seiji Suga

  DOI：10.1246/bcsj.20160135

  日期：2016.9.15

  We developed an acylative kinetic resolution of secondary carbinols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1d with tert-alcohol substituents. The reaction proceeded with a wide range of carbinols with moderate to high selectivity (s) (up to s = 79.5). Kinetic studies revealed that catalyst 1d was more catalytically active than the corresponding bis-methyl ether 1d′ or

  我们使用具有叔醇取代基的联萘基 N,N-4-二甲氨基吡啶 (DMAP) 衍生物 1d 开发了仲甲醇的酰化动力学拆分。反应在范围广泛的甲醇中进行，具有中到高的选择性 (s)（高达 s = 79.5）。动力学研究表明，催化剂 1d 比相应的双甲基醚 1d' 或 DMAP 具有更高的催化活性。催化剂的叔醇和仲甲醇之间的氢键是提高反应速率和高对映选择性的原因。