diethyl 2-(2-chlorophenyl)cyclopropane-1,1-dicarboxylate | 77094-96-3

• 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: diethyl 2-(2-chlorophenyl)cyclopropane-1,1-dicarboxylate
• CAS: 77094-96-3
• 化学式: C₁₅H₁₇ClO₄
• 分子量: 296.751
• InChiKey: POQOARFOWLHVRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-(2-chlorophenyl)cyclopropane-1,1-dicarboxylate 在 水 、 sodium hydroxide 、 potassium hydrogensulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以86%的产率得到2-(2-chlorophenyl)-1-(ethoxycarbonyl)cyclopropanecarboxylic acid
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones

  摘要：

  In the present study on the development of new anticonvulsants, twenty new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones were synthesized and tested for anticonvulsant activity using the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) screens. Their neurotoxicity was determined by the rotorod test. In this series, all of the alkyl- and aryl-substituted 5,5-cyclo-propanespirohydantoins showed more or less protection against MES and/or scPTZ models. The most active of the series was 6-methyl-1-(4-(methylsulfonyl)phenyl)-4,6-diazaspiro[2.4]heptane-5,7-dione (6t), which showed a MES ED50 value of 12.5 mg/kg in mice. The median toxic dose (TD50) was 310 mg/kg, providing compound 6t with a protection index (PI = TD50/ED50) of 24.8 in the MES test which is better than phenytoin. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.034
• 作为产物：
  描述：

  丙二酸二乙酯 在 dirhodium tetraacetate 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 5.08h， 生成 diethyl 2-(2-chlorophenyl)cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed [3 + 3] Cycloaddition of Cyclopropane 1,1-Diesters with Phthalazinium Dicyanomethanides

  摘要：

  The Sc(OTf)(3)-catalyzed diastereoselective [3 + 3] cycloaddition of phthalazinium dicyanomethanides with cyclopropane 1,1-diesters proceeded smoothly under mild reaction conditions, affording a variety of 3,4-dihydro-1H-pyrido[2,1-a]phthalazine derivatives in up to 99% yields with excellent diastereoselectivities.

  DOI：

  10.1021/acs.orglett.5b02003

文献信息

• Yb(OTf)₃ catalyzed [3 + 2] annulations of D–A cyclopropanes with β-oxodithioesters: a regioselective synthesis of tetrahydrothiophenes
  作者：Shu-Wen Wang、Wei-Si Guo、Li-Rong Wen、Ming Li

  DOI：10.1039/c5ra06355h

  日期：——

  An efficient approach to synthesis tetrahydrothiophenes was developed through the reaction of β-oxodithioesters and D–A cyclopropanes catalyzed by Yb(OTf)₃. This methodology was highly regioselective.

  通过Yb(OTf)₃催化的β-氧代二硫酸酯和D-A环丙烷的反应，开发了一种合成四氢噻吩的高效方法。这种方法具有很高的区域选择性。
• 一种采用芳基磺酰基苯甲醛腙对环丙烷化合 物开环的方法
  申请人：太原理工大学

  公开号：CN106083665B

  公开（公告）日：2018-08-03

  本发明公开了一种采用芳基磺酰基苯甲醛腙对环丙烷化合物发生开环反应的方法，是以1,1‑双酯‑2‑芳基环丙烷化合物为起始原料，使用芳基磺酰基苯甲醛腙做亲核试剂；在三氟甲磺酸金属类和卤代金属类双路易斯酸催化剂作用下，于苯类溶剂中发生环丙烷与腙的开环反应，反应温度为25～50℃，得到芳香脂肪多官能团化砜类产物。本发明反应过程操作简单，而且合成方法具有广泛的普适性，对于不同结构的双酯环丙烷和芳基磺酰基苯甲醛腙均可获得较高的收率。
• A metal-free BF₃·OEt₂ mediated chemoselective protocol for the synthesis of propargylic cyclic imines
  作者：Prasoon Raj Singh、Braj Gopal、Madan Kumar、Avijit Goswami

  DOI：10.1039/d2ob00530a

  日期：——

  chemoselective and metal/additive-free protocol for the synthesis of propargylic cyclic imine derivatives via (3 + 2)-cycloaddition of donor–acceptor cyclopropanes and alkynylnitriles in the presence of BF3·OEt2 has been established. The newly developed methodology provided access to a variety of propargylic cyclic imines in good to excellent yields. In addition, the synthesis of propargylic amines and the

  已经建立了在BF 3 ·OEt 2存在下通过供体-受体环丙烷和炔基腈的(3 + 2)-环加成合成炔丙基环状亚胺衍生物的化学选择性和无金属/无添加剂方案。新开发的方法提供了以良好至极好的收率获得各种炔丙基环状亚胺的途径。此外，还探索了从标题化合物合成炔丙基胺和相应的非常稳定的烯醇衍生物。
• Synthesis of Indole-Fused Dihydrothiopyrano Scaffolds <i>via</i> (3 + 3)-Annulations of Donor–Acceptor Cyclopropanes with Indoline-2-Thiones
  作者：Braj Gopal、Prasoon Raj Singh、Madan Kumar、Avijit Goswami

  DOI：10.1021/acs.joc.2c01990

  日期：2023.1.6

  A new methodology for the synthesis of N-haloindole-fused dihydrothiopyrano derivatives via (3 + 3)-annulation of donor–acceptor cyclopropanes (DACs) with indoline-2-thiones in the presence of Sc(OTf)3 as a Lewis acid catalyst has been developed. This protocol provides a variety of indole-fused dihydrothiopyrano molecules in good to excellent yields, which architecturally resemble other indole-fused

  在 Sc(OTf) 3作为路易斯酸催化剂存在下，通过供体-受体环丙烷 (DAC) 与二氢吲哚-2-硫酮的 (3 + 3)-环化合成N -卤代吲哚稠合二氢噻喃衍生物的新方法已经被开发出来。该协议提供了多种吲哚融合二氢硫代吡喃分子，产量高到极佳，其结构类似于其他具有潜在药用价值的吲哚融合三环分子。此外，我们还描述了详细的反应机制和将提供的产品转化为N-稠合噻嗪并吲哚分子。
• HFIP &amp; Brønsted Acid Promoted Direct Distal <i>C</i>‐Alkylation of 2‐Oxindoles and Anilines with Donor‐Acceptor Cyclopropanes
  作者：Prasoon Raj Singh、Manisha Lamba、Divyasha Singh、Avijit Goswami

  DOI：10.1002/adsc.202300165

  日期：2023.5.23

  in the aromatic ring via metal-free catalysis is very important. In this regard, we have developed a facile metal-free, extremely selective, user-friendly, environmentally benign and cost-effective Friedel-Crafts (FC) alkylation protocol for 2-oxindoles and anilines with donor-acceptor cyclopropanes. Real-time NMR studies reveal that the transformation is governed by the cooperative catalysis of Brønsted

  通过无金属催化在芳环的特定位置安装烷基链非常重要。在这方面，我们开发了一种简便的无金属、极具选择性、用户友好、环境友好且具有成本效益的 Friedel-Crafts (FC) 烷基化方案，用于 2-oxindoles 和苯胺与供体-受体环丙烷。实时核磁共振研究表明，这种转化受布朗斯台德酸 (TfOH) 和 HFIP 的协同催化控制，这促进了 2-羟吲哚和苯胺对供体-受体环丙烷的亲核攻击。