dimethyl 2-(2-fluorophenyl)cyclopropane-1,1-dicarboxylate | 1110700-49-6

• 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: dimethyl 2-(2-fluorophenyl)cyclopropane-1,1-dicarboxylate
• 英文别名: 2-(o-fluorophenyl)cyclopropane-1,1-dicarboxylate
• CAS: 1110700-49-6
• 化学式: C₁₃H₁₃FO₄
• 分子量: 252.242
• InChiKey: ZLKXGYYWPLNEOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(2-fluorophenyl)cyclopropane-1,1-dicarboxylate 、 N-氟代双苯磺酰胺 在 copper(l) iodide 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 以44 %的产率得到dimethyl 4-fluoro-3-(N-(phenylsulfonyl)phenylsulfonamido)-2,3-dihydro-1H-indene-1,1-dicarboxylate
  参考文献：
  名称：

  Divergent Copper‐salt‐controlled Reactions of Donor‐Acceptor Cyclopropanes and N ‐Fluorobenzene Sulfonimide: Access to the 1,3‐Haloamines and Aminoindanes

  摘要：

  AbstractWe herein report a method for divergent copper salt controlled reactions of donor‐acceptor cyclopropanes and N‐fluorobenzene sulfonimide (NFSI). Specifically, in the presence of CuX2 (X=Cl, Br), the cyclopropanes underwent formal umpolung 1,3‐aminohalogenation bifunctionalization via a free radical mediated ring‐opening process to afford 1,3‐aminochlorination and 1,3‐aminobromination products in moderate to good yields. In addition, by using CuI as a catalyst, we synthesized various aminoindane derivatives via 1,3‐aminoarylation cyclization of D‐A cyclopropanes, the reactions involved a free radical mediated ring‐opening and subsequent ring expansion via C−H bond activation.

  DOI：

  10.1002/chem.202202544
• 作为产物：
  描述：

  丙二酸二甲酯 在 哌啶 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 dimethyl 2-(2-fluorophenyl)cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  布朗斯台德酸在六氟异丙醇中催化的供体-受体环丙烷的亲核开环

  摘要：

  描述了一种在室温下布朗斯台德酸催化的方法，该方法用于室温下供体-受体环丙烷在氟化醇溶剂HFIP中的亲核开环。该方法的显着特征包括扩大的环丙烷范围，包括带有单个酮基受体的环丙烷和带有电子缺陷的芳基的环丙烷。值得注意的是，催化体系证明适用于多种亲核试剂，包括芳烃，吲哚，叠氮化物，二酮和醇。

  DOI：

  10.1021/acs.orglett.7b03688

文献信息

• Rhodium-Catalyzed Cyclopropanation of Alkenes with Dimethyl Diazomalonate
  作者：Francisco González-Bobes、Michaël D. B. Fenster、Susanne Kiau、Laxma Kolla、Sergei Kolotuchin、Maxime Soumeillant

  DOI：10.1002/adsc.200800027

  日期：2008.4.7

  α′-tetramethyl-1,3-benzenedipropanoate] to catalyze the cyclopropanation of a wide range of alkenes with malonate-derived carbenoids under mild reaction conditions is reported in this communication. The experimental protocol is remarkably simple, uses readily accessible and stable dimethyl diazomalonate with very low catalyst loading. More importantly, the alkene is employed as a limiting reagent.

  α，α，α'，α'-四甲基-1,3-苯二丙酸酯[Rh 2（esp）2；据报道，esp =α，α，α'，α'-四甲基-1,3-苯二丙酸酯]在温和的反应条件下与丙二酸酯衍生的类胡萝卜素催化多种烯烃的环丙烷化反应。实验方案非常简单，使用容易获得且稳定的重氮丙二酸二甲酯，催化剂的负载量非常低。更重要的是，烯烃被用作限制试剂。
• Lewis Acid Catalyzed Ring-Opening 1,3-Aminothiolation of Donor–Acceptor Cyclopropanes Using Sulfenamides
  作者：Avishek Guin、Thukaram Rathod、Rahul N. Gaykar、Tony Roy、Akkattu T. Biju

  DOI：10.1021/acs.orglett.0c00483

  日期：2020.3.20

  donor-acceptor (D-A) cyclopropanes using sulfenamides has been demonstrated. The insertion of the C-C σ-bond of D-A cyclopropanes into the S-N σ-bond of sulfenamides allows the synthesis of diverse γ-aminated α-thiolated malonic diesters in moderate to good yields (up to 87%) with good functional group compatibility. The stereospecificity of the reaction was demonstrated using enantiomerically pure D-A cyclopropane

  Yb（OTf）3使用亚磺酰胺催化了供体-受体（DA）环丙烷的轻度和区域选择性开环1,3-氨基硫醇化反应。将DA环丙烷的CCσ键插入次磺酰胺的SNσ键中，可以以中等至良好的收率（高达87％）以良好的官能团相容性合成各种γ胺化的α-硫代丙二酸二酯。使用对映体纯的DA环丙烷证明了反应的立体特异性。
• Cascade One-Pot Synthesis of Indanone-Fused Cyclopentanes from the Reaction of Donor-Acceptor Cyclopropanes and Enynals <i>via</i> a Sequential Hydrolysis/Knoevenagel Condensation/[3+2] Cycloaddition
  作者：Jiantao Zhang、Huanfeng Jiang、Shifa Zhu

  DOI：10.1002/adsc.201700345

  日期：2017.9.4

  to construct indanone‐fused cyclopentanes via a sequential hydrolysis/Knoevenagel condensation/[3+2] cycloaddition is reported. The desired indanone‐fused cyclopentanes were obtained in good yields. This method features mild reaction conditions and broad substrate scope, which render it very appealing to chemists for the synthesis of complex molecules containing an indanone‐fused cyclopentane moiety

  报道了通过顺序水解/ Knoevenagel缩合/ [3 + 2]环加成反应，供体-受体环丙烷与烯类的级联反应，以构建茚满酮稠合的环戊烷。以高收率获得了所需的茚满酮稠合的环戊烷。该方法具有温和的反应条件和广泛的底物范围，这使得它对于合成包含茚满酮稠合的环戊烷部分的复杂分子非常吸引化学家。此外，可以通过众所周知的转化将产物进一步转化为具有不同官能团的化合物。
• Sc(OTf)₃-Catalysed [3+3] Annulation of Cyclopropane 1,1-Diesters with Mercaptoacetaldehyde: A Facile Strategy for the Synthesis of Tetrahydrothiopyranols
  作者：Hua-Peng Wang、Huan-Huan Zhang、Xiu-Qin Hu、Peng-Fei Xu、Yong-Chun Luo

  DOI：10.1002/ejoc.201500282

  日期：2015.6

  A catalytic [3+3] annulation of cyclopropane 1,1-diesters with in-situ-generated mercaptoacetaldehyde for the synthesis of polyfunctionalized tetrahydrothiopyran derivatives has been developed. A ring-opening/aldol cascade reaction catalysed by Sc(OTf)(3) (10 mol-%) gave a series of tetrahydrothiopyranols in good yields. Simple derivatization of the products gave some useful compounds.

  已经开发了用于合成多官能化四氢噻喃衍生物的环丙烷 1,1-二酯与原位生成的巯基乙醛的催化 [3+3] 环化。由 Sc(OTf)(3) (10 mol-%) 催化的开环/醛醇级联反应以良好的产率得到了一系列四氢噻吩醇。产品的简单衍生得到一些有用的化合物。
• Sc(OTf)3-Catalyzed [3+3] Annulation of Cyclopropane 1,1-Diesters with β-(Indol-2-yl)-α,β-unsaturated Ketones: Synthesis of Polysubstituted Tetrahydrocarbazoles
  作者：Huan-Huan Zhang、Yong-Chun Luo、Wei Chen

  DOI：10.1055/s-0034-1380617

  日期：——

  A Sc(OTf)3-catalyzed cascade reaction consisting of a Friedel–Crafts alkylation followed by a Michael addition between cyclopropane 1,1-diesters and β-(indol-2-yl)-α,β-unsaturated ketones allows for the efficient synthesis of polysubstituted tetrahydrocarbazoles under very mild reaction conditions.

  Sc(OTf)3 催化的级联反应由 Friedel-Crafts 烷基化和环丙烷 1,1-二酯和 β-(indol-2-yl)-α,β-不饱和酮之间的迈克尔加成组成在非常温和的反应条件下合成多取代四氢咔唑。