2-(3,4-dichlorophenyl)-2-methyl-1,3-dioxolane | 1000788-58-8

• 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: 2-(3,4-dichlorophenyl)-2-methyl-1,3-dioxolane
• 英文别名: 2-(3,4-Dichlorophenyl)-2-methyl-1,3-dioxolane
• CAS: 1000788-58-8
• 化学式: C₁₀H₁₀Cl₂O₂
• 分子量: 233.094
• InChiKey: HBBROAUQJIRMFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2-(3,4-dichlorophenyl)-2-methyl-1,3-dioxolane 在 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 (3R)-5,6-dichloro-1,3-dimethyl-3,4-dihydroisoquinoline
  参考文献：
  名称：

  Expedient Synthesis of Highly Functionalised Cyclic Imines

  摘要：

  Aryl- and heteroaryl fused cyclic imines are obtained from the starting acetal via a directed metallation-alkylation-condensation sequence using cyclic sulfamidates as the electrophile. A variety of aromatics and heteroaromatics are demonstrated to be applicable to this methodology, which produces highly versatile cyclic imine building blocks for drug discovery and total synthesis programmes.

  DOI：

  10.1055/s-0034-1379918
• 作为产物：
  描述：

  乙二醇 、 3,4-二氯苯乙酮 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以91%的产率得到2-(3,4-dichlorophenyl)-2-methyl-1,3-dioxolane
  参考文献：
  名称：

  Lithiation of 2-(chloroaryl)-2-methyl-1,3-dioxolanes and application in synthesis of new ortho -functionalized acetophenone derivatives

  摘要：

  2-(4-Chlorophenyl)-2-methyl-1,3-dioxolane 2a was lithiated ortho to the ketal group by treatment with butyllithium in THF at 0degreesC. Related 2-aryl-2-methyl-1,3-dioxolanes possessing a chlorine substituent at the meta position of the aryl group 2b,c were lithiated with butyllithium in THF at -78degreesC at the position between the two directing groups. The lithio species thus generated were treated with various electrophiles to give ortho-functionalized acetophenone derivatives. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00391-5

文献信息

• Lithiation of 2-aryl-2-methyl-1,3-dioxolanes with PMDTA-complexed butyllithium
  作者：Bálint Nyulasi、András Németh、Márta Porcs-Makkay、József Kupai、Gyula Lukács、Gyula Simig、Balázs Volk

  DOI：10.1016/j.tet.2016.11.072

  日期：2017.1

  The lithio species thus generated were carboxylated to benzoic acids. Lithiations with BuLi occurred regioselectively ortho to the ketal substituent. When using BuLi/PMDTA, a regiodivergent behavior has generally been found in the lithiations. However, in some cases a significant selectivity was observed, enabling the preparation of the main regioisomer, exhibiting a new substitution pattern, with reasonable

  氯和甲氧基取代的苯乙酮缩酮的用丁基锂锂（BuLi），并与金属化Ñ，Ñ，Ñ '，Ñ “，Ñ ” -五甲基络合丁基锂（丁基锂/ PMDTA）进行了研究。由此产生的锂硫基物质被羧化为苯甲酸。与丁基锂Lithiations发生区域选择性邻位的缩酮取代。使用BuLi / PMDTA时，通常在锂化中发现了区域发散行为。然而，在某些情况下，观察到显着的选择性，从而能够制备主要的区域异构体，并显示出新的取代模式，且产率合理。
• Practical Synthesis of Variously Substituted 2,3,4-Benzothiadiazepine 2,2-Dioxides
  作者：Balázs Volk、Bálint Nyulasi、Tamara Teski、András Gy. Németh、Sára Sprőber、Gyula Simig

  DOI：10.1055/a-1797-5298

  日期：2022.7

  increased interest in this compound family. However, the literature of the closely related 2,3,4-benzothiadiazepine 2,2-dioxides is rather scarce. Earlier we elaborated a synthesis of 5-aryl congeners variously substituted at the aromatic ring. In the present study, a new synthetic route was investigated via highly versatile intermediates, to extend the reaction to a wider aromatic substitution pattern and

  2,3-benzodiazepine-4-ones 的显着药理活性导致人们对该化合物家族的兴趣增加。然而，密切相关的 2,3,4-苯并噻二氮杂 2,2-二氧化物的文献相当稀少。早些时候，我们详细阐述了芳环上不同取代的 5-芳基同系物的合成。在本研究中，通过高度通用的中间体研究了一种新的合成路线，将反应扩展到更广泛的芳族取代模式并制备 5-烷基和 5-H 衍生物。该方法的实质是，以苯甲醛缩醛、苯乙酮和二苯甲酮缩酮为原料，合成邻甲酰基和邻-酰基-芳基甲磺酰氯，它们是目标化合物的合适前体。合成如下进行：相应的缩醛和缩酮的邻位锂化和随后用多聚甲醛处理，或者用DMF或甲酸乙酯分两步处理，然后用NaBH 4还原，得到相应的羟甲基衍生物。后者与甲磺酰氯反应得到甲磺酸盐，该甲磺酸盐用于对硫脲进行S-烷基化以得到S-烷基异硫脲盐。合成的最后步骤在伸缩反应中进行。用N处理S-烷基异硫脲盐-氯代琥珀酰亚胺产生相
• Lithiation of 2-(chloroaryl)-2-methyl-1,3-dioxolanes and application in synthesis of new ortho -functionalized acetophenone derivatives
  作者：Gyula Lukács、Márta Porcs-Makkay、Gyula Simig

  DOI：10.1016/s0040-4039(03)00391-5

  日期：2003.4

  2-(4-Chlorophenyl)-2-methyl-1,3-dioxolane 2a was lithiated ortho to the ketal group by treatment with butyllithium in THF at 0degreesC. Related 2-aryl-2-methyl-1,3-dioxolanes possessing a chlorine substituent at the meta position of the aryl group 2b,c were lithiated with butyllithium in THF at -78degreesC at the position between the two directing groups. The lithio species thus generated were treated with various electrophiles to give ortho-functionalized acetophenone derivatives. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Expedient Synthesis of Highly Functionalised Cyclic Imines
  作者：Thomas Moss

  DOI：10.1055/s-0034-1379918

  日期：——

  Aryl- and heteroaryl fused cyclic imines are obtained from the starting acetal via a directed metallation-alkylation-condensation sequence using cyclic sulfamidates as the electrophile. A variety of aromatics and heteroaromatics are demonstrated to be applicable to this methodology, which produces highly versatile cyclic imine building blocks for drug discovery and total synthesis programmes.