methyl (1R,2S,3R,4S)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo(2.2.1)-5-hepten-2-ylcarboxylate | 144179-68-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R,2S,3R,4S)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo(2.2.1)-5-hepten-2-ylcarboxylate
• 英文别名: methyl (1R,2S,3R,4S)-3-[(4S)-4-(2,2-dimethyl-1,3-dioxolo)]bicyclo(2.2.1)-5-hepten-2-ylcarboxylate；methyl (1R,2S,3R,4S)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]bicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 144179-68-0
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: USDBKQWWJZGXCN-LVEVGFFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 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 (1R,2S,3R,4S)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo(2.2.1)-5-hepten-2-ylcarboxylate 在 盐酸 、 sodium periodate 、 lithium aluminium tetrahydride 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 生成 (1S,2R,3S,4R)-3-Benzyloxymethyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde
  参考文献：
  名称：

  Synthesis of a Rigid Diacylglycerol Analogue Having a Bis-γ-butyrolactone Skeleton Separated by a Cyclopentane Ring

  摘要：

  一种非常有效的方法被开发用于构建一个新的双γ-内酯系统，该系统基于环戊烯[1,2-c:3,4-c′]过氢二呋喃支架，所用的原料为环戊二烯和甲基(S)-(Z)-4,5-O-异丙基环戊-2-烯酸酯。

  DOI：

  10.1246/cl.1995.299
• 作为产物：
  描述：

  methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate 、 环戊二烯 反应 8.0h， 生成 methyl (1S,2S,3R,4R)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo(2.2.1)-5-hepten-2-ylcarboxylate 、 methyl (1R,2S,3R,4S)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo(2.2.1)-5-hepten-2-ylcarboxylate
  参考文献：
  名称：

  环戊二烯在（E）-和（Z）-（R）-4,5-二-O-异亚丙基-戊-2-烯酸酯中的未催化不对称diels-alder加成反应

  摘要：

  环戊二烯未催化的Diels-Alder加成到丙烯酸酯衍生物{= 1}时，具有高的非对映体和对映体选择性。

  DOI：

  10.1016/s0040-4039(00)98570-8

文献信息

• Enantioselective production of homochiral (+)-(1R,2S,3S,4S)- and (−)-(1S,2R,3R,4R)-bicyclo(2.2.1)heptane-2,3-dicarboxylic acid, 2-methyl esters. Formal synthesis of the TXA2 antagonist S-1452.
  作者：Ramon Casas、Rosa M. Oituõ

  DOI：10.1016/s0957-4166(00)82106-0

  日期：1992.9

  Both enantiomers of the title half ester have been synthesized from -mannitol as single chiral precursor. The -enantiomer is the key intermediate in the synthesis of the TXA2 antagonistic drug S-1452.

  标题半酯的两种对映体均由-甘露醇合成为单一手性前体。所述对映体是在TXA的合成中的关键中间体2拮抗药物S-1452。
• Asymmetric synthesis of 6-formyl-1-alkoxycarbonylbicyclo[3.1.0]hex-2-ene-2-carboxylic acids by a novel buffer-mediated rearrangement
  作者：Satomi Niwayama、Jianxiu Liu

  DOI：10.1016/s0957-4166(01)00430-x

  日期：2001.10

  Asymmetric synthesis of 6-formyl-1-alkoxycarbonylbicyclo[3.1.0]hex-2-ene-2-carboxylic acids has been achieved and the absolute configurations of the products of a novel buffer-mediated rearrangement have been established. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Diastereofacial selectivity in uncatalyzed Diels-Alder cycloadditions involving α,β-unsaturated esters and lactones with stereogenic centers containing oxygen functiionalities
  作者：Ramón Casas、Teodor Parella、Vicenç Branchadell、Antonio Oliva、Rosa M. Ortuño、André Guingant

  DOI：10.1016/s0040-4020(01)88527-6

  日期：1992.3

  Both experimental and theoretical studies on the Diels-Alder cycloadditions of dienophiles 1, 2 and 3 to different dienes show that the observed diastereofacial selectivity results from a combination of electronic and steric interactions. The traditional Felkin-Anh model is not appropriate for these cases. Several new chiral synthetic building blocks have been prepared.
• Lewis acid catalyzed Diels-Alder additions of cyclopentadiene to methyl (E)- and (Z)-(S)-4,5-di-O-isopropylidenepent-2-enoates: Rate and stereoselectivity.
  作者：Zhiyu Chen、Rosa M. Ortun˜o

  DOI：10.1016/s0957-4166(00)82295-8

  日期：1992.5

  Rate, and endo/exo and facial diastereostereoselectivity of the title reactions have been highly enhanced under the action of aluminum, among other metals used as catalysts, compared to the thermal processes. EtAlCl2 and Et2AlCl were the reagents that afforded the best results.
• Stereocontrolled synthetic entries to homochiral hydroxylated norbornene derivatives. Formal synthesis of some carbocyclic nucleosides.
  作者：Miguel Díaz、Javier Ibarzo、José M. Jiménez、Rosa M. Ortuño

  DOI：10.1016/s0957-4166(00)80493-0

  日期：1994.1

  Several homochiral hydroxylated norbornene derivatives have been synthesized from D-mannitol. Stereocontrolled Diels-Alder cycloadditions and stereospecific hydroxylations are key processes for the creation of the stereogenic centers in the target molecules. These compounds are real or potential precursors in the synthesis of carbocyclic nucleosides and related products.