diethyl 2-methyl-2-phenyl-1,1-cyclopropanedicarboxylate | 72174-97-1

• 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-methyl-2-phenyl-1,1-cyclopropanedicarboxylate
• 英文别名: 2-methyl-2-phenyl-cyclopropane-1,1-dicarboxylic acid diethyl ester；diethyl 2-methyl-2-phenylcyclopropane-1,1-dicarboxylate
• CAS: 72174-97-1
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: AQABNRXGBGPOST-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：
  0.5
• 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-methyl-2-phenyl-1,1-cyclopropanedicarboxylate 在 乙醇 、 sodium hydroxide 作用下， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis and SAR of 2-phenyl-1-sulfonylaminocyclopropane carboxylates as ADAMTS-5 (Aggrecanase-2) inhibitors

  摘要：

  A series of 1-sulfonylaminocyclopropanecarboxylates was synthesized as ADAMTS-5 (Aggrecanase-2) inhibitors. After an intensive investigation of the central cyclopropane core including its absolute stereochemistry and substituents, we found compound 22 with an Agg-2 IC(50) = 7.4 nM, the most potent ADAMTS-5 inhibitor reported so far. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.093
• 作为产物：
  描述：

  苯乙酮 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 8.5h， 生成 diethyl 2-methyl-2-phenyl-1,1-cyclopropanedicarboxylate
  参考文献：
  名称：

  S-Ethenylsulfoximine derivatives. Reagents for ethylenation of protic nucleophiles

  摘要：

  DOI：

  10.1021/jo01290a012

文献信息

• A practical and reusable catalyst for the synthesis of donor-acceptor cyclopropane
  作者：Yanqun Zhang、Manyu Jin、Cunqi Wu、Yongxia Zhao、Hua Zhou、Jingwei Xu

  DOI：10.1016/j.catcom.2017.09.009

  日期：2018.1

  donor-acceptor (D-A) cyclopropane via the cycloaddition of styrene derivatives with diethyl bromomalonate. A core-shell catalyst of Fe3O4@Cu2O is used to promote the construction of D-A cyclopropane with different functional groups in good yields. In our experiments, many harsh conditions, such as strict anhydrous and anaerobic, are avoided. The Fe3O4@Cu2O particles are easily made, air-stable and of low cost.

  在此，开发了一种方便，可回收且廉价的基于铜的催化系统，用于通过苯乙烯衍生物与溴代丙二酸二乙酯的环加成来合成供体-受体（DA）环丙烷。Fe 3 O 4 @Cu 2 O的核壳催化剂用于以良好的产率促进具有不同官能团的DA环丙烷的构建。在我们的实验中，避免了许多苛刻的条件，例如严格的无水和厌氧条件。Fe 3 O 4 @Cu 2 O颗粒易于制造，空气稳定且成本低廉。而且，磁性使催化剂易于分离，即使循环使用五次，催化活性也没有明显变化。
• Cyclopropane compounds and pharmaceutical use thereof
  申请人：Inaba Takashi

  公开号：US20060199826A1

  公开（公告）日：2006-09-07

  The present invention provides a compound having aggrecanase inhibitory activity and MMP-13 inhibitory activity, and useful as a therapeutic agent for osteoarthritis, rheumatoid arthritis and the like, more specifically, a cyclopropane compound of formula (1): wherein R 1 is —(CH 2 ) m —X—(CH 2 ) n -A 1 etc., wherein m and n are the same or different and each is 0 to 6, X 1 is a single bond, etc. and A 1 is a substituted C 3-14 hydrocarbon ring group, etc.; R 2 and R 3 are the same or different and each is a hydrogen atom, —(CH 2 ) p —X 1 -(CH 2 ) q -A 2 , etc., wherein p and q are the same or different and each is 0 to 6, X 1 is a single bond, etc. and A 2 is an optionally substituted C 3-14 hydrocarbon ring group, etc.; R 4 is —CO 2 R 9 , etc., wherein R 9 is a hydrogen atom, etc.; and R 20 and R 21 are the same or different and each is a hydrogen atom, —(CH 2 ) m12 —X 12 —(CH 2 ) m12 —R 30 , etc., wherein m12 and m12 are the same or different and each is 0 to 6, X 12 is a single bond, etc. and R 30 is a hydrogen atom, etc.; or a prodrug thereof or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有抗软骨素酶活性和MMP-13抑制活性的化合物，可用作治疗骨关节炎、类风湿性关节炎等疾病的治疗剂，更具体地，是一种环丙烷化合物，其化学式为（1）：其中，R1为—（CH2）m—X—（CH2）n-A1等，其中m和n相同或不同，且每个为0至6，X1为单键等，A1为取代的C3-14碳氢环基等；R2和R3相同或不同，且每个为氢原子，—（CH2）p—X1-（CH2）q-A2等，其中p和q相同或不同，且每个为0至6，X1为单键等，A2为可选取代的C3-14碳氢环基等；R4为—CO2R9等，其中R9为氢原子等；且R20和R21相同或不同，且每个为氢原子，—（CH2）m12—X12—（CH2）m12—R30等，其中m12和m12相同或不同，且每个为0至6，X12为单键等，R30为氢原子等；或其前药或其药学上可接受的盐。
• CYCLOPROPANE COMPOUNDS AND PHARMACEUTICAL USE THEREOF
  申请人：INABA Takashi

  公开号：US20080261994A1

  公开（公告）日：2008-10-23

  The present invention provides a compound having aggrecanase inhibitory activity and MMP-13 inhibitory activity, and useful as a therapeutic agent for osteoarthritis, rheumatoid arthritis and the like, more specifically, a cyclopropane compound of formula (1): wherein R 1 is —(CH 2 ) m —X—(CH 2 ) n -A 1 etc., wherein m and n are the same or different and each is 0 to 6, X is a single bond, etc. and A 1 is a substituted C 3-14 hydrocarbon ring group, etc.; R 2 and R 3 are the same or different and each is a hydrogen atom, —(CH 2 ) p —X 1 —(CH 2 ) q -A 2 , etc., wherein p and q are the same or different and each is 0 to 6, X 1 is a single bond, etc. and A 2 is an optionally substituted C 3-14 hydrocarbon ring group, etc.; R 4 is —CO 2 R 9 , etc., wherein R 9 is a hydrogen atom, etc.; and R 20 and R 21 are the same or different and each is a hydrogen atom, —(CH 2 ) m12 —X 12 —(CH 2 ) m12 —R 30 , etc., wherein m12 and m12 are the same or different and each is 0 to 6, X 12 is a single bond, etc. and R 30 is a hydrogen atom, etc.; or a prodrug thereof or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有抑制aggrecanase和MMP-13活性的化合物，可用作治疗骨关节炎，类风湿性关节炎等疾病的治疗剂，更具体地说，是式（1）的环丙烷化合物：其中，R1为—（CH2）m—X—（CH2）n-A1等，其中m和n相同或不同，每个为0至6，X为单键等，A1为取代的C3-14烃环基等；R2和R3相同或不同，每个为氢原子，—（CH2）p—X1—（CH2）q-A2等，其中p和q相同或不同，每个为0至6，X1为单键等，A2为可选取代的C3-14烃环基等；R4为—CO2R9等，其中R9为氢原子等；以及R20和R21相同或不同，每个为氢原子，—（CH2）m12—X12—（CH2）m12—R30等，其中m12和m12相同或不同，每个为0至6，X12为单键等，R30为氢原子等；或其前药或其药学上可接受的盐。
• Electrocatalytic Synthesis of 1,2-Dioxolanes from Tetrasubstituted Donor–Acceptor Cyclopropanes
  作者：Gwyndaf A. Oliver、Simon Kolb、Daniel B. Werz

  DOI：10.1055/a-2179-6320

  日期：——

  2-dioxolanes from donor–acceptor cyclopropanes with quaternary donor positions is described. This catalyst-free strategy delivers radical cations after C(sp3)–C(sp3) cleavage by direct anodic oxidation of the strained carbocycle. A broad scope with regard to the cyclopropanes employed in the reaction is presented. Additionally, we propose a plausible mechanism for the reaction.

  描述了一种从具有四元供体位置的供体-受体环丙烷合成 3,3,5,5-四取代 1,2-二氧戊环的电化学方法。这种无催化剂策略通过应变碳环的直接阳极氧化在 C(sp3)–C(sp3) 裂解后提供自由基阳离子。给出了反应中使用的环丙烷的广泛范围。此外，我们提出了一种合理的反应机制。
• [EN] CYCLOPROPANE COMPOUNDS AND PHARMACEUTICAL USE THEREOF<br/>[FR] COMPOSES DE CYCLOPROPANE ET UTILISATION PHARMACEUTIQUE DE CEUX-CI
  申请人：JAPAN TOBACCO INC

  公开号：WO2005058884A3

  公开（公告）日：2005-09-09