methyl 2-[2-(1,3-dioxolan-2-yl)ethyl]propenoate | 144800-73-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-[2-(1,3-dioxolan-2-yl)ethyl]propenoate
• 英文别名: Methyl 4-(1,3-dioxolan-2-yl)-2-methylidenebutanoate
• CAS: 144800-73-7
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: KQBCGEJIFRYCBL-UHFFFAOYSA-N

物化性质

• 沸点：
  250.5±15.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  methyl 2-[2-(1,3-dioxolan-2-yl)ethyl]propenoate 在 四(三苯基膦)钯 盐酸 、 4-二甲氨基吡啶 、 二异丁基氢化铝 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 methyl cis-[2(1,3-benzodioxol-5-yl)-4-methylene-2-nitrocyclohexyl]acetate
  参考文献：
  名称：

  通过顺序六元环反应η 3 π-烯丙基烷基化-迈克尔加成

  摘要：

  钯催化bisfunctional电体的缩合16，与1,3-二酮17或arylnitromethane衍生物7，导致加合物18和20分别通过涉及顺序过程η 3 π-烯丙基烷基化-迈克尔加成。硝酸酯20构成了合成赤藓生物碱的有用潜在前体。

  DOI：

  10.1016/s0040-4039(97)10833-4
• 作为产物：
  描述：

  2-(4'-N,N-Dimethyl-3'-carbomethoxybutyl)-1,3-dioxolane 在 diazabicyclononene 作用下， 以 甲醇 、 苯 为溶剂， 反应 20.5h， 生成 methyl 2-[2-(1,3-dioxolan-2-yl)ethyl]propenoate
  参考文献：
  名称：

  X = Y - ZH systems as potential 1,3-dipoles part 35. Generation of nitrones from oximes. Class 3 processes. Tandem intramolecular michael addition (1,3-azaprotio cyclotransfer) - intermolecular 1,3-dipolar cycloaddition reactions.

  摘要：

  Aldoximes and ketoximes possessing gamma- or delta-alkenyl substituents undergo thermal conversion to 5- and 6- membered cyclic nitrones via a 1,3-azaprotio cyclotransfer, a 2n + 2-sigma + 2-pi concerted process, rather than a Michael addition. The reactions can be performed as a tandem nitrone formation-cycloaddition sequence or, if required, the intermediate nitrones can be isolated. The cycloadditions usually proceed via an exo-transition state and show both regio- and diastereofacial-specificity. Preliminary attempts at chiral induction via a menthyl auxiliary are reported.

  DOI：

  10.1016/s0040-4020(01)89883-5

文献信息

• The six-membered annulation reaction involving sequential palladium-catalyzed allylic alkylation and Michael addition: scope and limitations
  作者：Céline Jousse-Karinthi、Fatima Zouhiri、Jacqueline Mahuteau、Didier Desmaële

  DOI：10.1016/s0040-4020(03)00186-8

  日期：2003.3

  The palladium-catalyzed condensation of a variety of active methylene compounds with methyl 6-acetoxymethyl-hepta-2,6-dienoate was investigated. The six-membered adducts resulting from a η3 palladium complex alkylation–Michael addition sequence were obtained with moderate to good yields. In some cases, further evolution of the primary adduct was observed. The process has been expanded to access nitrogen

  研究了多种活性亚甲基化合物与6-乙酰氧基甲基庚-2,6-二烯酸甲酯的钯催化缩合反应。从所得η六元加合物3具有中度至良好的产率获得了钯配合物的烷基化-迈克尔加成序列。在某些情况下，观察到主要加合物的进一步发展。通过使用对甲苯磺酰胺钠作为亲核伙伴，该方法已扩展为可接近氮杂环。
• Synthetic Application of Sequential Palladium-Catalyzed Allylic Acetate Alkylation and Michael Addition Carbocyclization: Synthesis of (±)-Dihydroerythramine
  作者：Céline Jousse-Karinthi、Claude Riche、Angèle Chiaroni、Didier Desmaële

  DOI：10.1002/1099-0690(200110)2001:19<3631::aid-ejoc3631>3.0.co;2-8

  日期：2001.10

  (Nitromethyl)arene 3 underwent a palladium-catalyzed annulation reaction with allylic acetate 11 to provide nitro esters 12a and 12b by an (η3-allyl)palladium complex alkylation/Michael addition domino sequence. Reduction of the nitro group of 12a, followed by cyclization of the resulting amino group on the acetate appendage, afforded the bicyclic lactam 29. Two-carbon elongation at the nitrogen atom of 29 by hetero

  报道了一种合成芳香刺桐生物碱的新途径。（硝基甲基）芳烃 3 与乙酸烯丙酯 11 进行钯催化的环化反应，通过（η3-烯丙基）钯配合物烷基化/迈克尔加成多米诺骨牌序列提供硝基酯 12a 和 12b。将 12a 的硝基还原，然后将所得氨基在乙酸酯附属物上环化，得到双环内酰胺 29。通过乙烯基苯基亚砜的杂迈克尔加成，接着是 Pummerer-，在 29 的氮原子处发生双碳延伸型环化，得到 cis-11-phenylthioerythrinan-8-one (32a, 32b) 以及重排的内酰胺 34。C-11 处的还原脱硫和 C-3 环外双键的氧化裂解得到 15,16-(亚甲二氧基)erythrinan-3,8-dione (42)。
• X = Y - ZH systems as potential 1,3-dipoles part 35. Generation of nitrones from oximes. Class 3 processes. Tandem intramolecular michael addition (1,3-azaprotio cyclotransfer) - intermolecular 1,3-dipolar cycloaddition reactions.
  作者：Ronald Grigg、Jasothara Markandu、Trevor Perrior、Sivagnanasundram Surendrakumar、William J. Warnock

  DOI：10.1016/s0040-4020(01)89883-5

  日期：1992.1

  Aldoximes and ketoximes possessing gamma- or delta-alkenyl substituents undergo thermal conversion to 5- and 6- membered cyclic nitrones via a 1,3-azaprotio cyclotransfer, a 2n + 2-sigma + 2-pi concerted process, rather than a Michael addition. The reactions can be performed as a tandem nitrone formation-cycloaddition sequence or, if required, the intermediate nitrones can be isolated. The cycloadditions usually proceed via an exo-transition state and show both regio- and diastereofacial-specificity. Preliminary attempts at chiral induction via a menthyl auxiliary are reported.
• Six-membered annulation reaction by sequential η3-allylpalladium alkylation-Michael addition
  作者：Céline Jousse、Delphine Mainguy、Didier Desmaële

  DOI：10.1016/s0040-4039(97)10833-4

  日期：1998.3

  bisfunctional electrophile 16, with 1,3 dione 17 or arylnitromethane derivative 7, led to adducts 18 and 20 respectively, through a sequential process involving η3-allylpalladium alkylation-Michael addition. Nitro ester 20 constitutes useful potential precursor for the synthesis of Erythrina alkaloids.

  钯催化bisfunctional电体的缩合16，与1,3-二酮17或arylnitromethane衍生物7，导致加合物18和20分别通过涉及顺序过程η 3 π-烯丙基烷基化-迈克尔加成。硝酸酯20构成了合成赤藓生物碱的有用潜在前体。