(4R)-4-carbomethoxy-3-methoxy-4-methyl-2,5-cyclohexadien-1-one | 105880-83-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: (4R)-4-carbomethoxy-3-methoxy-4-methyl-2,5-cyclohexadien-1-one
• 英文别名: methyl (1R)-2-methoxy-1-methyl-4-oxocyclohexa-2,5-diene-1-carboxylate
• CAS: 105880-83-9
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: URWJTVJWFJBKDS-SNVBAGLBSA-N

物化性质

• 沸点：
  309.6±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-4-carbomethoxy-3-methoxy-4-methyl-2,5-cyclohexadien-1-one 生成 6-carbomethoxy-4-methoxy-6-methylbicyclo[3.1.0^1,5]hex-3-en-2-one
  参考文献：
  名称：

  SCHULTZ A. G.; LAVIERI F. P.; MACIELAG M., TETRAHEDRON LETT., 27,(1986) N 13, 1481-1484

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-(-)-methyl 2-methoxy-1-methyl-2,5-cyclohexadiene-1-carboxylate 在 重铬酸吡啶 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 (4R)-4-carbomethoxy-3-methoxy-4-methyl-2,5-cyclohexadien-1-one
  参考文献：
  名称：

  2,5-Cyclohexadien-1-one 到双环 [3.1.0] 己烯酮光重排。用于有机合成的反应的发展

  摘要：

  Le mecanisme le plus plausible fait intervenir un zwitterion de preferred a un biradicalorganique

  DOI：

  10.1021/ja00247a027

文献信息

• PLE and HLE catalyzed reverse enantiomeric separation of (±)-methyl-2-methoxy-1-methyl-2,5-cyclohexadiene-1-carboxylate derivatives
  作者：Cihangir Tanyeli、Bengu Sezen、Ayhan S Demir、Rosemeire Brondi Alves、Simeon Arseniyadis

  DOI：10.1016/s0957-4166(99)00080-4

  日期：1999.3

  We describe the diversities of hydrolase-type enzymes PLE and HLE on the hydrolysis of (+/-)-methyl-2-methoxy-1 -methyl-2,5-cyclohexadiene-1-carboxylate and (+/-)-methyl-2-methoxy-1 -methyl-2,5-cyclohexadiene-4-one-1-carboxylate to afford both enantiomers with 92-96% ee. (C) 1999 Elsevier Science Ltd. All rights reserved.
• SCHULTZ, A. G.;LAVIERI, F. P.;MACIELAG, M.;PLUMMER, M., J. AMER. CHEM. SOC., 109,(1987) N 13, 3991-4000
  作者：SCHULTZ, A. G.、LAVIERI, F. P.、MACIELAG, M.、PLUMMER, M.

  DOI：——

  日期：——
• Substituent effects on the photorearrangements of 4-alkoxy-4-carbomethoxy-3-methoxy-2,5-cyclohexadien-1-ones
  作者：Arthur G. Schultz、Roger E. Harrington

  DOI：10.1021/jo00022a033

  日期：1991.10

  Enantiomerically enriched 4-carbomethoxy-3,4-dimethoxy-2,5-cyclohexadien-1-one (1) undergoes a completely diastereoselective (but not enantiospecific) type A photorearrangement at 366 nm to give 6-carbomethoxy-4,6-dimethoxybicyclo[3.1.0(1,5)]hex-3-en-2-one (2) in 81% isolated yield. A chiral NMR shift study indicates that 1 undergoes partial loss of absolute configuration at C(4) during irradiation. Bicyclohexenone 2 is photostable at 366 nm but rearranges to its diastereoisomer 3 and phenols 4 and 5 at > 300 nm. It is proposed that ground-state conformational effects control the type A photoreactivity of 1 and that rearrangement to 2 occurs in accord with the principle of least motion in the transition states for rearrangements to diastereomerically related zwitterions 1a and 1b (Scheme III). The intramolecular 2 + 2 photocycloaddition of 4-carbomethoxy-3-methoxy-4-(1'-oxa-3'-butenyl)-2,5-cyclohexadien-1-one (9) gives a mixture of 7-oxatricyclodecenones 10 (58%) and 11 (18%), without interference from type A photoreactivity.
• The regioselectivity and stereoselectivity of the photorearrangement of 3-methoxy-4- methoxycarbonyl-4-methyl-2,5-cyclohexadien-1-one
  作者：Arthur G. Schultz、Frank P. Lavieri、Mark Macielag

  DOI：10.1016/s0040-4039(00)84290-2

  日期：1986.1