trans-ethyl-2,2-dimethoxy-3-methylcyclopropane-1-carboxylate | 130307-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-ethyl-2,2-dimethoxy-3-methylcyclopropane-1-carboxylate
• 英文别名: Ethyl 2,2-dimethoxy-3-methylcyclopropane-1-carboxylate
• CAS: 130307-20-9
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: BRQVWVDQCXJKSK-UHFFFAOYSA-N

物化性质

• 沸点：
  203.1±40.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  trans-ethyl-2,2-dimethoxy-3-methylcyclopropane-1-carboxylate 生成 ethyl 4,4-dimethoxy-3-methylbut-3-enoate
  参考文献：
  名称：

  GRAZIANO, M. LILIANA;CIMMINIELLO, GUIDO

  摘要：

  DOI：
• 作为产物：
  描述：

  重氮乙酸乙酯 、 甲基烯酮二甲基缩醛 在 copper acetylacetonate 作用下， 以 苯 为溶剂， 反应 0.33h， 生成 trans-ethyl-2,2-dimethoxy-3-methylcyclopropane-1-carboxylate
  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
• 作为试剂：
  描述：

  cis ethyl 5,5-dimethoxy-4-methyl-1-phenyl-2-thioxopyrrolidine-3-carboxylate 在 trans-ethyl-2,2-dimethoxy-3-methylcyclopropane-1-carboxylate 作用下， 反应 96.0h， 以70%的产率得到ethyl 5-methoxy-4-methyl-2-methylthio-1-phenylpyrrole-3-carboxylate
  参考文献：
  名称：

  Graziano, M. L.; Cimminiello, Guido, Journal of Chemical Research, Miniprint, 1989, # 2, p. 446 - 457

  摘要：

  DOI：

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。
• PROCESS FOR PRODUCING ISOXAZOLINE DERIVATIVES
  申请人：FANG GUANGYU

  公开号：US20160060223A1

  公开（公告）日：2016-03-03

  A process for producing isoxazoline derivatives by ring-opening and cyclization of the corresponding cyclopropane derivatives with electrophilic nitrosylation reagents.

  一种通过使用亲电性亚硝基化试剂对相应环丙烷衍生物进行环丙烷环开和环化反应制备异氧杂环丙烷衍生物的方法。
• 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).