ethyl 3-ethyl-2,2-dimethoxycyclopropanecarboxylate | 101944-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-ethyl-2,2-dimethoxycyclopropanecarboxylate
• 英文别名: Ethyl 3-ethyl-2,2-dimethoxycyclopropane-1-carboxylate
• CAS: 101944-76-7
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: UQFCYZBCPUWXOX-UHFFFAOYSA-N

物化性质

• 沸点：
  70-71 °C(Press: 4 Torr)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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 、 ethyl 3-ethyl-2,2-dimethoxycyclopropanecarboxylate 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到ethyl 2-ethyl-3-methoxy-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
• 作为产物：
  描述：

  重氮乙酸乙酯 、 1,1-dimethoxy-but-1-ene 在 copper acetylacetonate 作用下， 以 苯 为溶剂， 反应 0.33h， 以75%的产率得到ethyl 3-ethyl-2,2-dimethoxycyclopropanecarboxylate
  参考文献：
  名称：

  Reactions of Ketenes; XIX¹. A General Method for the Synthesis of 4,4.4-Trialkoxybutanoic Esters

  摘要：

  DOI：

  10.1055/s-1985-31338

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。
• Highly Diastereoselective Synthesis of<i>cis</i>-2,3-Disubstituted γ-Lactones by the Reaction of 2,2-Dialkoxy-3-alkylcyclopropanecarboxylic Esters with Symmetric Ketones
  作者：Kazuhiko Saigo、Shigeru Shimada、Yukihiko Hashimoto、Tadamichi Nagashima、Masaki Hasegawa

  DOI：10.1246/cl.1990.1101

  日期：1990.7

  In the presence of titanium(IV) chloride, 2,2-dialkoxy-3-alkylcyclopropanecarboxylic esters reacted with symmetric ketones to give cis-2,3-disubstituted γ-lactones with high diastereoselectivity. The resulting cis-lactones were easily converted into trans-isomers by treatment with a catalytic amount of sodium ethoxide.

  在氯化钛 (IV) 存在下，2,2-二烷氧基-3-烷基环丙烷羧酸酯与对称酮反应生成具有高非对映选择性的顺式-2,3-二取代 γ-内酯。通过用催化量的乙醇钠处理，所得顺式内酯很容易转化为反式异构体。
• Diastereoselective Claisen Condensation-Type Reactions of Alkyl 2,2-Dialkoxycyclopropanecarboxylates with Esters and Acid Chlorides Promoted by Titanium(IV) Chloride
  作者：Shigeru Shimada、Kazuhiko Saigo、Yukihiko Hashimoto、Yasunari Maekawa、Takashi Yamashita、Taketsugu Yamamoto、Masaki Hasegawa

  DOI：10.1246/cl.1991.1475

  日期：1991.8

  In the presence of titanium(IV) chloride, alkyl 2,2-dialkoxycyclopropane carboxylates reacted with esters and acid chlorides to give Claisen condensation-type products. The reaction essentially proceeded with extremely high diastereoselectivity.

  在氯化钛 (IV) 存在下，2,2-二烷氧基环丙烷羧酸烷基酯与酯和酰氯反应生成克莱森缩合型产物。该反应基本上以极高的非对映选择性进行。
• 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).
• GRAZIANO, M. LILIANA;CIMMINIELLO, GUIDO
  作者：GRAZIANO, M. LILIANA、CIMMINIELLO, GUIDO

  DOI：——

  日期：——