1,1-dimethoxy-2,2-diphenylethane | 51936-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1-dimethoxy-2,2-diphenylethane
• 英文别名: diphenylacetaldehyde dimethylacetal；(2,2-dimethoxyethane-1,1-diyl)dibenzene；Benzene, 1,1'-(2,2-dimethoxyethylidene)bis-；(2,2-dimethoxy-1-phenylethyl)benzene
• CAS: 51936-06-2
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: CNGKBZHGTPJYEL-UHFFFAOYSA-N

物化性质

• 沸点：
  302.0±37.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-dimethoxy-2,2-diphenylethane 在 吡啶 、 三甲基氯硅烷 、 氯化亚砜 、 cobalt(II) chloride 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 17.75h， 生成 trans-2-benzhydryl-4-(2-chloroethyl)-1,3-dioxolane
  参考文献：
  名称：

  1,3-Dioxane as a scaffold for potent and selective 5-HT1AR agonist with in-vivo anxiolytic, anti-depressant and anti-nociceptive activity

  摘要：

  A series of compounds generated by ring expansion/opening and molecular elongation/simplification of the 1,3-dioxolane scaffold were prepared and tested for binding affinity at 5-HT1AR and alpha(1) adrenoceptors. The compounds with greater affinity were selected for further functional studies. N4(2,2-dipheny1-1,3-dioxan-5-yl)methyl)-2-(2-methoxyphenoxy)ethan-1-ammonium hydrogen oxalate (12) emerged as highly potent full agonist at the 5-HT1AR (pKi 5-HT1A = 8.8; pD(2) = 9.22, %E-max = 92). The pharmacokinetic data in rats showed that the orally administered 12 has a high biodistribution in the brain compartment. Thus, 12 was further investigated in-vivo, showing an anxiolytic and antidepressant effect. Moreover, in the formalin test, 12 was able to decrease the late response to the noxious stimulus, indicating a potent1Al use in the treatment of chronic pain. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.05.024
• 作为产物：
  描述：

  [dichloro-[(1R,2R)-2-methoxy-1,2-diphenylethyl]-λ4-selanyl]benzene 以50%的产率得到
  参考文献：
  名称：

  TIECCO, MARCELLO;TESTAFERRI, LORENZO;TINGOLI, MARCO;CHIANELLI, DONATELLA;+, TETRAHEDRON, 44,(1988) N 8, 2261-2272

  摘要：

  DOI：

文献信息

• Methoxychlorination and dimethoxylation of alkenes the reactions of substituted styrenes with phenylselenenyl chloride in methanol
  作者：Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli、Donatella Chianelli、Donatella Bartoli

  DOI：10.1016/s0040-4020(01)81734-8

  日期：1988.1

  addition of PhSeCl to α- and β-substituted styrenes in methanol is regio- and stereospecific and affords the products of methoxyselenenylation. These compounds further react with PhSeCl to give the deselenenylation products. In the case of α-substituted styrenes, 1-methoxy, 2-chloroalkanes are produced, whereas with β-substituted styrenes the major reaction products are the 1,2-dimethoxyalkanes and

  在甲醇中向α-和β-取代的苯乙烯中添加PhSeCl具有区域和立体特异性，并提供甲氧基硒烯化的产物。这些化合物进一步与PhSeCl反应，得到去硒烯基化产物。在α-取代的苯乙烯的情况下，产生了1-甲氧基，2-氯代烷烃，而对于β-取代的苯乙烯，主要的反应产物是发生苯基迁移的1,2-二甲氧基烷烃和2,2-二甲氧基烷烃。结果表明，这些反应是通过中间形成烷基苯基氯化二苯酚PhCR（OMe）CHR 1 SeCl 2 Ph来进行的，而中间反应机理取决于起始烯烃的结构。
• Hypoiodous acid-catalyzed regioselective geminal addition of methanol to vinylarenes: synthesis of anti-Markovnikov methyl acetals
  作者：Swamy Peraka、Naresh Mameda、Mahender Reddy Marri、Srujana Kodumuri、Durgaiah Chevella、Prabhakar Sripadi、Narender Nama

  DOI：10.1039/c5ra16826k

  日期：——

  salt and oxone is reported. The preliminary mechanistic investigations suggest that the key factor for achieving the anti-Markovnikov regioselectivity is the semipinacol rearrangement of an iodo functionalized intermediate, which is confirmed by an isotope labeling experiment. In addition, the reaction involves the de-iodination of a co-iodo intermediate via its oxidation to hypervalent iodine species

  报道了一种新的无金属的，乙烯基芳烃的催化双甲氧基化的乙烯基芳烃，其基于从碘化物盐和氧酮原位生成的HOI物质。初步的机理研究表明，实现抗马尔科夫尼科夫区域选择性的关键因素是碘官能化中间体的频哪醇重排，这通过同位素标记实验得以证实。此外，该反应涉及的去碘化共碘中间经由氧化成高价碘，而不是由亲电试剂将其抽象为碘化物。HRESI-MS研究支持在芳族烯烃催化转化为相应的缩醛的过程中，将含一价碘的中间体转化为三价碘的中间体。
• Epoxide ring-opening and Meinwald rearrangement reactions of epoxides catalyzed by mesoporous aluminosilicates
  作者：Mathew W. C. Robinson、A. Matthew Davies、Richard Buckle、Ian Mabbett、Stuart H. Taylor、Andrew E. Graham

  DOI：10.1039/b900719a

  日期：——

  Mesoporous aluminosilicates efficiently catalyze the ring-opening of epoxides to produce β-alkoxyalcohols in high yields under extremely mild reaction conditions. These materials also catalyze the corresponding Meinwald rearrangement in non-nucleophilic solvents to give aldehydes which can be trapped in situ to provide the corresponding acetals in an efficient tandem process.

  介孔铝硅酸盐可在极温和的反应条件下高效催化环氧化物的开环反应，从而以高收率生产β-烷氧基醇。这些材料还可以在非亲核溶剂中催化相应的Meinwald重排，从而生成可以在有效的串联过程中原位捕获以提供相应的缩醛的醛。
• FeCl₃·6H₂O-Catalyzed Mukaiyama-Aldol Type Reactions of Enolizable Aldehydes and Acetals
  作者：Alejandra Rodríguez-Gimeno、Ana B. Cuenca、Jesús Gil-Tomás、Mercedes Medio-Simón、Andrea Olmos、Gregorio Asensio

  DOI：10.1021/jo501498a

  日期：2014.9.5

  stable catalyst, lead to β-methoxycarbonyl compounds with nearly quantitative yields. The methodology is extended to the parent aldehydes as starting materials, leading to the corresponding aldols with lower yields, but efficiently. Different alkyl and aryl substituted acetals and aldehydes have been tested in the reaction with linear and cyclic silyl enol ethers. Reactions are carried out in an open air

  衍生自可烯化醛的缩醛的Mukaiyama-aldol型缩醛与环保，低成本且稳定的催化剂FeCl 3 ·6H 2 O生成的β-甲氧基羰基化合物的收率接近定量。该方法已扩展到母体醛作为起始原料，从而导致相应的醛醇缩合物的收率较低，但效率很高。在与直链和环状甲硅烷基烯醇醚的反应中，已经测试了不同的烷基和芳基取代的缩醛和醛。反应在露天气氛中进行，不需要添加剂。在这种类型的FeCl 3 ·6H 2 O催化的缩合反应中，缩醛可以被认为是羰基部分的活化基团，而不是保护基团。
• HNTf₂-Catalyzed Regioselective Preparation of Polysubstituted Naphthalene Derivatives Through Alkyne–Aldehyde Coupling
  作者：Sudipta Ponra、Maxime R. Vitale、Véronique Michelet、Virginie Ratovelomanana-Vidal

  DOI：10.1021/acs.joc.5b00353

  日期：2015.3.20

  We report herein the preparation of polysubstituted naphthalene derivatives by the original Brønsted-acid-catalyzed benzannulation reaction of phenylacetaldehydes with alkynes. This reaction, which was usually performed with Lewis acids under thermal activation, is efficiently promoted by 15 mol % of triflimide (HNTf2) at room temperature under metal-free and mild reaction conditions and leads with

  我们在这里报道了通过苯乙醛与炔烃的原始布朗斯台德酸催化苯环化反应制备多取代的萘​​衍生物。通常在无金属和温和的反应条件下，室温下用15摩尔％的三氟甲酰亚胺（HNTf 2）可以有效地促进该反应，该反应通常用路易斯酸在热活化下进行。官能化萘的收率为41–78％。提出了催化循环以及该催化体系在环氧化物和乙缩醛衍生物的相关苯环化转化中的一些进一步应用。