(1R,2R,3R)-(+)-oxalic acid 2-ethoxycarbonyl-3-formylcyclopropyl ester methyl ester | 953419-58-4

• 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: (1R,2R,3R)-(+)-oxalic acid 2-ethoxycarbonyl-3-formylcyclopropyl ester methyl ester
• 英文别名: (1R,2R,3R)-2-(ethoxycarbonyl)-3-formylcyclopropyl methyl oxalate；2-O-[(1R,2R,3R)-2-ethoxycarbonyl-3-formylcyclopropyl] 1-O-methyl oxalate
• CAS: 953419-58-4
• 化学式: C₁₀H₁₂O₇
• 分子量: 244.201
• InChiKey: FMRNUFSFKBDNPL-FSDSQADBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R)-(+)-oxalic acid 2-ethoxycarbonyl-3-formylcyclopropyl ester methyl ester 在 叔丁基过氧化氢 、 正丁基锂 、 silver hexafluoroantimonate 、 三氟化硼乙醚 、 Pd(quinox)Cl₂ 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 46.25h， 生成 (4R,5R)-5-(2-methyl-5-oxocyclopent-1-en-1-yl)-3-methylene-4-((R)-3-oxo-1-((triisopropylsilyl)oxy)butyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Arteludovicinolide A的两种对映异构体的不对称合成

  摘要：

  报道了Arteludovicinolide A任一对映异构体的首次全合成及其生物学评估，其特征为具有4-位立体异构侧链的γ-丁内酯的不对称构建的新策略。从可再生资源2-糠酸甲酯开始，倍半萜烯内酯通过不对称环丙烷化和两个非对映选择性亲核试剂的加成，通过9个步骤和4.8％的总收率进行合成，利用供体-受体-环丙烷-内酯化级联反应。在非细胞毒性浓度（≤10μM）（+） - 1被发现具有较高的15倍的抗炎活性（4.87±1.1μM）比以前为≥45μM浓度的报道。

  DOI：

  10.1021/ol401473v
• 作为产物：
  描述：

  2-糠酸甲酯 在 copper(II) bis(trifluoromethanesulfonate) 、 (R,R)-(+)-2,2'-异亚丙基双(4-叔丁基-2-恶唑啉) 、 臭氧 、 苯肼 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,2R,3R)-(+)-oxalic acid 2-ethoxycarbonyl-3-formylcyclopropyl ester methyl ester
  参考文献：
  名称：

  Facile Asymmetric Synthesis of the Core Nuclei of Xanthanolides, Guaianolides, and Eudesmanolides

  摘要：

  Bicylic and tricyclic gamma-butyrolactones with 5,7-, 5,6,5-, 5,6,6-, or 5,7,5-fused ring systems, being found in xanthanolides, eudesmanolides, and guaianolides, were readily synthesized from methyl furan-2-carboxylic acid. Key steps were a copper(I)-catalyzed asymmetric cyclopropanation, Sakurai allylations, intramolecular ene reactions, and ring-closing metathesis reactions.

  DOI：

  10.1021/ol034141s

文献信息

• Stereoselective routes to aryl substituted γ-butyrolactones and their application towards the synthesis of highly oxidised furanocembranoids
  作者：Allan Patrick G. Macabeo、Andreas Kreuzer、Oliver Reiser

  DOI：10.1039/c1ob05113j

  日期：——

  Titanium chelate addition of aryl nucleophiles to cyclopropyl aldehyde 6 followed by a tin-catalyzed one-pot retro-aldol, acetalisation and lactonisation sequence afforded cis and trans γ-aryllactone acetals. A γ-furyllactone derived by this approach was further transformed in two steps to model compounds for the oxidised northeastern sectors of selected Pseudopterogorgia diterpenoids.

  钛螯合物将芳基亲核试剂螯合加成到环丙基醛6上，然后进行锡催化的一锅逆向羟醛缩醛的缩醛化和内酯化，得到顺式和反式γ-芳基内酯缩醛。通过这种方法得到的γ-呋喃内酯在两个步骤中被进一步转化，以对选定的拟鞭毛虫二萜类化合物的东北东北部氧化化合物建模。
• Enantioselective Synthesis of Arglabin
  作者：Srinivas Kalidindi、Won Boo Jeong、Andreas Schall、Rakeshwar Bandichhor、Bernd Nosse、Oliver Reiser

  DOI：10.1002/anie.200701584

  日期：2007.8.20
• Diastereoselective Synthesis of Enantiopure γ-Butenolide-butyrolactones towards Pseudopterogorgia Lactone Furanocembranoid Substructures
  作者：Oliver Reiser、Allan Macabeo、Christian Lehmann

  DOI：10.1055/s-0032-1317555

  日期：——

  A diastereoselective methodology for preparing trans-gamma-lactone-gamma-butenolides through vinylogous aldol additions of siloxy-furanes to enantiopure cyclopropylcarbaldehyde followed by a tin-catalyzed retroaldol-lactonization cascade is reported. This synthetic approach is applied to a short synthesis of an exo-trienol furan lactone substructure relevant to bielschowskysin and other related coral diterpenoid natural products.
• Facile Asymmetric Synthesis of the Core Nuclei of Xanthanolides, Guaianolides, and Eudesmanolides
  作者：Bernd Nosse、Rakeshwar B. Chhor、Won Boo Jeong、Claudius Böhm、Oliver Reiser

  DOI：10.1021/ol034141s

  日期：2003.3.1

  Bicylic and tricyclic gamma-butyrolactones with 5,7-, 5,6,5-, 5,6,6-, or 5,7,5-fused ring systems, being found in xanthanolides, eudesmanolides, and guaianolides, were readily synthesized from methyl furan-2-carboxylic acid. Key steps were a copper(I)-catalyzed asymmetric cyclopropanation, Sakurai allylations, intramolecular ene reactions, and ring-closing metathesis reactions.
• Asymmetric Synthesis of Both Enantiomers of Arteludovicinolide A
  作者：Andreas Kreuzer、Sabine Kerres、Thomas Ertl、Hannelore Rücker、Sabine Amslinger、Oliver Reiser

  DOI：10.1021/ol401473v

  日期：2013.7.5

  their biological evaluation is reported, featuring a new strategy for the asymmetric construction of γ-butyrolactones with stereogenic side chains in the 4-position. Starting from the renewable resource methyl 2-furoate, the sesquiterpene lactone was synthesized in 9 steps and 4.8% overall yield via an asymmetric cyclopropanation and two diastereoselective nucleophile additions making use of a donor-

  报道了Arteludovicinolide A任一对映异构体的首次全合成及其生物学评估，其特征为具有4-位立体异构侧链的γ-丁内酯的不对称构建的新策略。从可再生资源2-糠酸甲酯开始，倍半萜烯内酯通过不对称环丙烷化和两个非对映选择性亲核试剂的加成，通过9个步骤和4.8％的总收率进行合成，利用供体-受体-环丙烷-内酯化级联反应。在非细胞毒性浓度（≤10μM）（+） - 1被发现具有较高的15倍的抗炎活性（4.87±1.1μM）比以前为≥45μM浓度的报道。