diethyl cis-2-methyl-3-phenyl-1,1-cyclopropanedicarboxylate | 75228-42-1

• 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 cis-2-methyl-3-phenyl-1,1-cyclopropanedicarboxylate
• 英文别名: 1,1-diethoxycarbonyl-cis-2-methyl-3-phenylcyclopropane；diethyl (2S,3S)-2-methyl-3-phenylcyclopropane-1,1-dicarboxylate
• CAS: 75228-42-1；75228-43-2
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: VZFYDMCKLNWYQG-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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 cis-2-methyl-3-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：

  重氮丙酸二乙酯 、 顺-β-甲基苯乙烯 在 copper octadecanoate 作用下， 以34%的产率得到diethyl cis-2-methyl-3-phenyl-1,1-cyclopropanedicarboxylate
  参考文献：
  名称：

  Mandel'shtam, T. V.; Kolesova, S. V.; Polina, T. V., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 1024 - 1031

  摘要：

  DOI：

文献信息

• Synthesis of gem-dialkoxycarbonylcyclopropane derivatives from olefins by the reaction with dibromomalonic esters and copper in dimethyl sulphoxide
  作者：Nariyoshi Kawabata、Masami Tanimoto

  DOI：10.1016/0040-4020(80)88047-1

  日期：1980.1

  A novel method for the synthesis of gem-dialkoxycarbonylcyclopropane derivatives is reported which involves the reaction of olefins with dibromomalonic esters and Cu in dimethyl sulphoxide. The reaction was applicable to a wide range of olefins and proceeded smoothly at moderate temperature to give the cyclopropane derivatives often in good yields. Cu was converted to Cu(II) bromide during the reaction

  报道了合成宝石-二烷氧基羰基环丙烷衍生物的新方法，该方法涉及烯烃与二溴丙二酸酯和Cu在二甲基亚砜中的反应。该反应适用于各种烯烃，并在中等温度下平稳地进行，从而经常以良好的收率得到环丙烷衍生物。在反应过程中，Cu转化为溴化Cu（II）。该反应是弱亲电的并且非立体特异性地进行，并且涉及添加和消除的逐步机理似乎对该反应是有利的。相反，在先前报道的有机宝石对烯烃进行环丙烷化的例子中-二卤化物和芳香族烃中的Cu，Cu转化为Cu（I）卤化物，类胡萝卜素中间体的协同环加成似乎是有利的。
• A New Cyclopropanation Method Mediated by Organosulfur Compounds
  作者：Jun-ichi Ohishi

  DOI：10.1055/s-1980-29171

  日期：——
• Mandel'shtam, T. V.; Kolesova, S. V.; Polina, T. V., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 1024 - 1031
  作者：Mandel'shtam, T. V.、Kolesova, S. V.、Polina, T. V.、Solomentsev, V. V.、Osmolovskaya, N. S.

  DOI：——

  日期：——
• Synthesis and SAR of 2-phenyl-1-sulfonylaminocyclopropane carboxylates as ADAMTS-5 (Aggrecanase-2) inhibitors
  作者：Makoto Shiozaki、Hiroto Imai、Katsuya Maeda、Tomoya Miura、Katsutaka Yasue、Akira Suma、Masahiro Yokota、Yosuke Ogoshi、Julia Haas、Andrew M. Fryer、Ellen R. Laird、Nicole M. Littmann、Steven W. Andrews、John A. Josey、Takayuki Mimura、Yuichi Shinozaki、Hiromi Yoshiuchi、Takashi Inaba

  DOI：10.1016/j.bmcl.2009.08.093

  日期：2009.11

  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.