methyl (1R*,2R*,6R*,7R*)-11,11-dimethoxy-3-oxa-10-oxotricyclo[5.2.2.0^2,6]undec-8-en-8-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R*,2R*,6R*,7R*)-11,11-dimethoxy-3-oxa-10-oxotricyclo[5.2.2.0^2,6]undec-8-en-8-carboxylate
• 英文别名: methyl (1S,2S,6S,7S)-11,11-dimethoxy-10-oxo-3-oxatricyclo[5.2.2.02,6]undec-8-ene-8-carboxylate
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: HHMUBRPIEXAVGF-ASXGKARISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 methyl (1R*,2R*,6R*,7R*)-11,11-dimethoxy-3-oxa-10-oxotricyclo[5.2.2.0^2,6]undec-8-en-8-carboxylate 在 sodium methylate 作用下， 反应 2.0h， 以81%的产率得到(3aS,4S,7aR)-4-(Dimethoxy-methoxycarbonyl-methyl)-2,3,3a,4,7,7a-hexahydro-benzofuran-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Remote controlled Haller–Bauer ring opening of bicyclo[2.2.2]octenones

  摘要：

  A new, unprecedented case of the Haller-Bauer reaction in bicyclo[2.2.2]octenones, easily obtained from the Diels-Alder reaction, provides effective and stereocontrolled access to highly substituted cyclohexene derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02267-x
• 作为产物：
  描述：

  2,3-二氢呋喃 、 3,3-Dimethoxy-4-oxo-cyclohexa-1,5-dienecarboxylic acid methyl ester 在 碘苯二乙酸 作用下， 以 甲醇 为溶剂， 反应 1.67h， 以70%的产率得到methyl (1R*,2R*,6R*,7R*)-11,11-dimethoxy-3-oxa-10-oxotricyclo[5.2.2.0^2,6]undec-8-en-8-carboxylate
  参考文献：
  名称：

  掩蔽的邻苯并醌对反电子需求的亲二烯体的反应。烯醇和硫烯醇醚为亲二烯体

  摘要：

  描述了掩蔽的邻苯并醌和富电子的亲二烯体如烯醇醚和硫烯醇醚的狄尔斯-阿尔德反应。

  DOI：

  10.1016/s0040-4039(99)01753-0

文献信息

• Inverse-electron-demand Diels–Alder reactions of masked o-benzoquinones with enol ethers and styrene
  作者：Shih-Yu Gao、San Ko、Yen-Lin Lin、Rama Krishna Peddinti、Chun-Chen Liao

  DOI：10.1016/s0040-4020(00)00937-6

  日期：2001.1

  stereoslective inverse-electron-demand Diels–Alder reactions of masked o-benzoquinones (MOBs) 1a–1h derived from the corresponding 2-methoxyphenols 2a–2h with benzyl vinyl ether, dihydrofuran and styrene to afford the highly functionalized bicyclo[2.2.2]octenone derivatives are described. The MOBs having electron-deficient substituents were found to undergo more facile Diels–Alder cycloadditions with these dienophiles

  由相应的2-甲氧基苯酚2a - 2h衍生的掩蔽邻苯甲醌1a - 1h与苄基乙烯基醚，二氢呋喃和苯乙烯的区域和立体选择反电子需求的Diels-Alder反应与苄基乙烯基醚，二氢呋喃和苯乙烯[2.2] [2]描述了辛烯酮衍生物。发现具有缺电子取代基的MOB与这些亲二烯体进行的更容易的Diels-Alder环加成反应。富含电子的亲双烯体二氢吡喃不是MOB的合适的2π伴侣。尝试根据前沿分子轨道理论解释这些Diels-Alder环加成物的区域化学。
• Gao, Shih-Yu; Lin, Yen-Lin; Rao, Polisetti Dharma, Synlett, 2000, # 3, p. 421 - 423
  作者：Gao, Shih-Yu、Lin, Yen-Lin、Rao, Polisetti Dharma、Liao, Chun-Chen

  DOI：——

  日期：——
• Reaction of masked o-benzoquinones towards dienophiles with inverse electronic demand. Enol and thioenol ethers as dienophiles
  作者：Odón Arjona、Rocío Medel、Joaquín Plumet

  DOI：10.1016/s0040-4039(99)01753-0

  日期：1999.11

  The Diels-Alder reaction of masked o-benzoquinones and electron-rich dienophiles such as enol ethers and thioenol ethers is described.

  描述了掩蔽的邻苯并醌和富电子的亲二烯体如烯醇醚和硫烯醇醚的狄尔斯-阿尔德反应。
• Remote controlled Haller–Bauer ring opening of bicyclo[2.2.2]octenones
  作者：Odón Arjona、Rocı́o Medel、Joaquı́n Plumet

  DOI：10.1016/s0040-4039(00)02267-x

  日期：2001.2

  A new, unprecedented case of the Haller-Bauer reaction in bicyclo[2.2.2]octenones, easily obtained from the Diels-Alder reaction, provides effective and stereocontrolled access to highly substituted cyclohexene derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.