syn-2-methoxy-1,2-diphenylethanol | 50778-88-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: syn-2-methoxy-1,2-diphenylethanol
• 英文别名: threo-2-methoxy-1,2-diphenylethanol；trhre-1,2-Diphenyl-2-methoxyethanol；2-methoxy-1,2-diphenylethan-1-ol；2-methoxy-1,2-diphenylethanol；(+/-)-threo-α'-methoxy-bibenzyl-α-ol；(1R,2R)-2-methoxy-1,2-diphenylethanol
• CAS: 50778-88-6
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: DAUUWYCGIFAYBG-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  syn-2-methoxy-1,2-diphenylethanol 生成 (+/-)-threo-α-acetoxy-α'-methoxy-bibenzyl
  参考文献：
  名称：

  Epoxyethers. III. Reaction of Desyl Chloride with Base

  摘要：

  DOI：

  10.1021/ja01112a030
• 作为产物：
  描述：

  安息香甲基醚 在 aluminum isopropoxide 、 异丙醇 作用下， 生成 syn-2-methoxy-1,2-diphenylethanol
  参考文献：
  名称：

  Satellite-based detection of Canadian boreal forest fires: Development and application of the algorithm

  摘要：

  This study presents a comprehensive investigation of fires across the Canadian boreal forest zone by means of satellite-based remote sensing. A fire-detection algorithm was designed to monitor fires using daily Advanced Very High Resolution Radiometer (AVHRR) images. It exploits information from multichannel AVHRR measurements to determine the locations of fires on satellite pixels of about 1 km(2) under clear sky or thin smoke cloud conditions. Daily fire maps were obtained showing most of the active fires across Canada (except those obscured by thick clouds). This was achieved by first compositing AVHRR scenes acquired over Canada on a given day and then applying the fire-detection algorithm. For the fire seasons of 1994-1998, about 800 NOAA/AVHRR daily mosaics were processed. The results provide valuable nation-wide information on fire activities in terms of their locations, burned area, starting and ending dates, as well as development. The total burned area as detected by satellite across Canada is estimated to be approximately 3.9, 4.9, 1.3, 0.4 and 2.4 million hectares in 1994, 1995, 1996, 1997 and 1998, respectively. The peak month of burning varies considerably from one year to another between June and August, as does the spatial distribution of fires. In general, conifer forests appear to be more vulnerable to burning and fires tend to grow larger than in deciduous forests.

  DOI：

  10.1080/01431160050144956
• 作为试剂：
  描述：

  2,3-bis(phenylsulfonyl)norbornadiene 在 正丁基锂 、 syn-2-methoxy-1,2-diphenylethanol 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 、 乙醚 为溶剂， 以72%的产率得到(1R,3R,4S)-3-Benzenesulfonyl-bicyclo[2.2.1]hept-5-en-2-one
  参考文献：
  名称：

  手性醇在多环双（苯磺酰基）烯烃脱对称中的Li +和Na +对映选择性开关

  摘要：

  在多环双（苯磺酰基）烯烃的不对称反应中，通过将碱从n -BuLi变为NaH的变化，可以实现对映选择性的完全转换，从而可以方便地获得具有相同手性助剂的多环酮的对映异构体。

  DOI：

  10.1016/s0040-4039(00)01261-2

文献信息

• Scandium-Bipyridine-Catalyzed, Enantioselective Alcoholysis ofmeso-Epoxides
  作者：Andreas Tschöp、Andreas Marx、Anakallil R. Sreekanth、Christoph Schneider

  DOI：10.1002/ejoc.200601101

  日期：2007.5

  The scandium-bipyridine-catalyzed ring-opening of meso-epoxides with aliphatic alcohols has been studied. Aromatic epoxides were ring-opened with >90 % ee furnishing valuable 1,2-diol monoethers in typically good yields whereas aliphatic epoxides gave rise to moderate enantioselectivities. The catalyst loading may be lowered to 2–5 mol-% with only marginal effects on yield and enantioselectivity. A

  已经研究了钪-联吡啶催化的内消旋环氧化物与脂肪醇的开环。芳香族环氧化物以> 90% ee 开环，以通常良好的产率提供有价值的1,2-二醇单醚，而脂肪族环氧化物产生中等的对映选择性。催化剂负载量可以降低到 2-5 mol-%，对产率和对映选择性的影响很小。观察到强烈的正非线性效应，表明手性催化剂的聚集现象。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007）
• Isothiourea-Catalysed Sequential Kinetic Resolution of Acyclic (±)-1,2-Diols
  作者：Siegfried Harrer、Mark D. Greenhalgh、Rifahath M. Neyyappadath、Andrew D. Smith

  DOI：10.1055/s-0037-1610721

  日期：2019.8

  The isothiourea-catalysed acylative kinetic resolution of a range of acyclic (±)-1,2-diols using 1 mol% of catalyst under operationally simple conditions is reported. Significantly, the bifunctional nature of (±)-1,2-diols was exploited in a sequential double kinetic resolution, in which both kinetic resolutions operate synergistically to provide access to highly enantioenriched products. The principles

  报告了在操作简单的条件下使用 1 mol% 催化剂对一系列无环 (±)-1,2-二醇进行异硫脲催化的酰化动力学拆分。值得注意的是，(±)-1,2-二醇的双功能特性在连续双动力学拆分中得到了利用，其中两种动力学拆分协同运作以提供对高度对映体富集的产品的访问。讨论了支持该过程的原理，并在模型系统中报告了各个动力学拆分步骤的选择性因素。
• Lewis acid-promoted electron transfer deoxygenation of epoxides, sulfoxides, and amine N-oxides: the role of low-valent niobium complexes from NbCl5 and Zn
  作者：Kyungsoo Oh、William Eric Knabe

  DOI：10.1016/j.tet.2009.02.013

  日期：2009.4

  A mild and operationally simple deoxygenation of epoxides, sulfoxides, and amine N-oxides is described using a sub-stoichiometric amount of low-valent niobium complexes generated in situ from commercially available NbCl5 and zinc dust. The deoxygenation proceeds by a reductive cleavage of polarized O–C/O–N/O–S bonds through a single electron transfer from zinc metal to the niobium–substrate complex

  使用亚化学计量量的由市售NbCl 5和锌粉原位生成的低价铌络合物，描述了对环氧化合物，亚砜和胺N-氧化物进行温和且简单的脱氧的方法。由于铌物种的高亲氧性，单价电子从锌金属转移到铌-底物络合物，使极化的O-C / O-N / O-S键还原性裂解，从而进行脱氧。相邻的自由基稳定基团的存在对环氧底物是有利的。但是，类似的前提条件不适用于亚砜和胺N-氧化物，在这些亚胺和N-胺胺中，各种底物均能以优异的产率有效地脱氧。
• Highly Enantioselective Ring‐Opening of <i>meso‐</i> Epoxides with O‐ and <i>N‐</i> Nucleophiles Catalyzed by a Chiral Sc(III)/bipyridine Complex
  作者：Štefan Malatinec、Eva Bednářová、Hiroki Tanaka、Martin Kotora

  DOI：10.1002/ejoc.202001493

  日期：2021.2.25

  A newly designed ligand with the bipyridine scaffold (an analog of Bolm's ligand), in combination with Sc(OTf)3, exhibits high stereocontrol in the ring opening of meso‐epoxides with various alcohols providing 1,2‐alkoxyalcohols.

  新设计的配体与联吡啶骨架（Bolm的配体的类似物），结合钪（OTF）3，表现出的开环高立体控制的内消旋环氧化物与各种醇提供1,2-烷氧基醇。
• Studies aimed at enhancement of reactivity and enantioselectivity of a lithium ester enolate using a chiral tridentate lithium amide
  作者：Mostafa Ahmed Hussein、Akira Iida、Kiyoshi Tomioka

  DOI：10.1016/s0040-4020(99)00644-4

  日期：1999.9

  chiral amines 7–13 mediated the asymmetric condensation reaction of lithium ester enolate 2 with benzaldehyde p-anisidine imine 3 giving the corresponding β-lactam 4 in up to 75% ee. It became apparent that coexistence of 2 and chiral lithium amides derived from 7–13 is an important factor for the enhancement of the reactivity and enantioselectivity of 2.

  三齿手性胺7-13介导了烯醇锂酯2与苯甲醛对茴香胺亚胺3的不对称缩合反应，从而在75％ee内产生相应的β-内酰胺4。它变得明显的共存2个衍生自和手性氨基化锂7-13为的反应性和对映选择性的的提高的一个重要因素2。