methyl 2,2-dimethoxy-3-methylcyclopropanecarboxylate | 131287-02-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,2-dimethoxy-3-methylcyclopropanecarboxylate
• 英文别名: Methyl 2,2-dimethoxy-3-methylcyclopropane-1-carboxylate
• CAS: 131287-02-0
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: MSUJQDGAZGNPBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(叔丁基二甲基硅氧基)-1-甲氧基乙烯 、 methyl 2,2-dimethoxy-3-methylcyclopropanecarboxylate 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到methyl 3-methoxy-2-methyl-5-oxocyclopent-3-ene-1-carboxylate
  参考文献：
  名称：

  路易斯酸介导的 2,2-二烷氧基环丙烷羧酸酯与乙烯酮甲硅烷基缩醛的反应。环戊烯酮的合成

  摘要：

  由氯化钛 (IV) 介导的 2,2-二烷氧基环丙烷羧酸酯与烯酮甲硅烷基缩醛的新型 [3+2] 型反应得到 3-烷氧基-2-（或-3-）环戊烯酮衍生物。

  DOI：

  10.1246/cl.1990.1093

文献信息

• Diastereoselective ring-opening aldol-type reaction of 2,2-dialkoxycyclopropanecarboxylic esters with carbonyl compounds. 2. Synthesis of cis-2,3-substituted-γ-lactones
  作者：Shigeru Shimada、Yukihiko Hashimoto、Tadamichi Nagashima、Masaki Hasegawa、Kazuhiko Saigo

  DOI：10.1016/s0040-4020(01)80347-1

  日期：——

  The reaction of 3-alkyl-2,2-dialkoxycyclopropanecarboxylic esters 1d–i with symmetrical ketones and formaldehyde was investigated. Cyclopropanes 1d–i react with symmetrical ketones and formaldehyde in the presence of TiCl4 to give cis-2,3-substituted-γ-lactones in good yields with high diastereoselectivity. In the reaction of 3-ethylcyclopropane 1d, the reaction conditions hardly influenced the diastereoselectivity

  研究了3-烷基-2,2-二烷氧基环丙烷羧酸酯1d–i与对称酮和甲醛的反应。环丙烷1D-我具有对称酮和甲醛在的TiCl的存在下反应4，得到顺式-2,3-取代的γ内酯以良好的收率与高非对映选择性。在3-乙基环丙烷1d的反应中，反应条件几乎不影响非对映选择性。但是，关于3-甲基环丙烷1f的反应，观察到反应条件，特别是溶剂对非对映选择性的影响。1d反应也观察到高化学选择性用1，4-环己二酮单-乙缩醛（24）。通过用NaOEt在EtOH中处理使顺式-γ-内酯异构化，得到高产率的反式异构体。
• Ring-opening aldol-type reaction of 2,2-dialkoxycyclopropanecarboxylic esters with carbonyl compounds. 3. The diastereoselective synthesis of 2,3,4-trisubstituted .gamma.-lactones
  作者：Shigeru Shimada、Yukihiko Hashimoto、Kazuhiko Saigo

  DOI：10.1021/jo00071a036

  日期：1993.9

  The Lewis acid-promoted reaction of 3-alkyl-2,2-dialkoxycyclopropanecarboxylic esters 1d-h with aldehydes to give 2,3,4-trisubstituted gamma-lactones was investigated. The diastereoselectivity of this reaction is highly dependent on the catalyst employed. Thus while the ZrCl4-promoted reaction gave (2alpha,3alpha,4beta)-trisubstituted gamma-lactones in good yields with excellent selectivity, the SnBr4-promoted reaction was moderately selective for (2alpha,3alpha,4alpha)-trisubstituted gamma-lactones. The present reaction was applied to the synthesis of (+)589- and (-)589-dihydropertusaric acid (26). Comparison of the spectroscopic and physical data of synthetic 26 with those of a 4-alkyl-3-carboxy-2-methyl gamma-lactone isolated from the lichen Pertusaria albescens revealed that the relative stereochemistry of the natural gamma-lactone was not (2beta,3beta,4alpha), as reported by Huneck and his co-workers, but rather (2beta,3alpha,4alpha); that is, the natural gamma-lactone was not (-)589-dihydropertusaric acid (26), but (-)589-pertusarinic acid (27).
• SAIGO, KAZUHIKO;SHIMADA, SHIGERU;SHIBASAKI, TOSHIFUMI;HASEGAWA, MASAKI, CHEM. LETT.,(1990) N, C. 1093-1096
  作者：SAIGO, KAZUHIKO、SHIMADA, SHIGERU、SHIBASAKI, TOSHIFUMI、HASEGAWA, MASAKI

  DOI：——

  日期：——