methyl cis-2-(2-methylpropen-1-yl)cyclopropane-1-carboxylate | 120143-45-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl cis-2-(2-methylpropen-1-yl)cyclopropane-1-carboxylate
• 英文别名: (1R,3S)-(+)-Chrysanthemumsaeure-methylester；methyl (1S,2S)-2-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• CAS: 120143-45-5
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: CUZGYCYYWNSLPC-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-4-Hydroxy-5-methyl-hex-2-ynoic acid 在 Lindlar's catalyst 二苯甲酮 、 氢气 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 69.0h， 生成 methyl cis-2-(2-methylpropen-1-yl)cyclopropane-1-carboxylate
  参考文献：
  名称：

  Franck-Neumann, Michel; Sedrati, Madjid; Vigneron, Jean-Paul, Angewandte Chemie, 1985, vol. 97, # 11, p. 995 - 996

  摘要：

  DOI：

文献信息

• Semicorrin metal complexes as enantioselective catalysts. Part 2. Enantioselective cyclopropane formation from olefins with diazo compounds catalyzed by chiral (semicorrinato)copper complexes
  作者：Hugo Fritschi、Urs Leutenegger、Andreas Pfaltz

  DOI：10.1002/hlca.19880710621

  日期：1988.9.28

  were obtained (Table 2). Usually, the reactions were carried out using bis(semicorrinato)copper(II) complexes as precatalysts. In order to produce active catalysts, these complexes had to be activated first by heating in the presence of diazoacetate or by treatment with phenylhydrazine. Experiments with (semicorrinato)copper(I) complexes, prepared in situ from copper(I) tert-butoxide (Scheme 4), suggest

  发现手性，C 2对称半corrin配体的铜配合物是从烯烃与重氮化合物形成环丙烷的有效催化剂。在催化剂的1％模式下，重氮乙酸烷基酯与末端烯烃如苯乙烯，丁二烯和1-庚烯平稳地反应，得到相应的光学活性环丙烷羧酸衍生物（表1方案2）。使用其中一种催化剂，对映选择性高达97％ee （表2）。通常，该反应使用双（准corrinato）铜（II）配合物作为预催化剂进行。为了生产活性催化剂，必须首先通过在重氮乙酸酯存在下加热或通过苯肼处理来活化这些配合物。使用由叔丁醇铜（I）原位制备的（semicorrinato）铜（I）配合物进行的实验（方案4）表明，实际的催化剂是[单（semicorrinarinato）]铜（I）。
• Effective Uses of Dirhodium(II) Tetrakis[methyl 2-oxopyrrolidine-5(R or S)-carboxylate] for Highly Enantioselective Intermolecular Cyclopropenation Reactions
  作者：Michael P. Doyle、Marina Protopopova、Paul Muller、Doina Ene、Evgeny A. Shapiro

  DOI：10.1021/ja00098a009

  日期：1994.9

  The title compounds are effective catalysts for intermolecular cyclopropenation reactions of l-alkynes with diazo esters and diazo amides. Diastereoselectivities achieved from the appropriate match with d- or l-menthyl diazoacetate are 77 to greater than or equal to 94% de. Enantioselectivities up to greater than or equal to 94% ee with 3-methoxy-1-propyne and 3,3-diethoxy-1 -propyne have been obtained. Variations in these values for metal carbene additions to alkynes are associated with electronic and/or steric influences from the alkyne or carbene substituents. N,N-Dimethyldiazoacetamide provides a higher level of enantiocontrol than do diazo esters. The absolute configurations of the cyclopropene products have been established; dirhodium(II) tetrakis[methyl 2-oxopyrrolidine-5(S)-carboxylate], Rh-2(5S-MEPY)(4), produces 2-substituted-2-cyclopropene-1-carboxylates having the (S)-configuration whereas use of Rh-2(5R-MEPY)(4) provides these cyclopropene products in the (R)-configuration. Diimide reduction of these cyclopropenecarboxylates produces the cis-disubstituted cyclopropane products exclusively.
• Franck-Neumann, Michel; Sedrati, Madjid; Vigneron, Jean-Paul, Angewandte Chemie, 1985, vol. 97, # 11, p. 995 - 996
  作者：Franck-Neumann, Michel、Sedrati, Madjid、Vigneron, Jean-Paul、Bloy, Vincente

  DOI：——

  日期：——