Maleinsaeure-mono-(1'R,3'R,4'S)-3-menthylester | 92419-65-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Maleinsaeure-mono-(1'R,3'R,4'S)-3-menthylester
• 英文别名: maleic acid mono-l-menthyl ester；mono-(-)-menthyl maleic acid；((1R)-menthyl)-hydrogen maleate；Maleinsaeure-mono-((1R)-menthylester)；((1R)-Menthyl)-hydrogenmaleinat；(Z)-3-(1R,2S,5R)-((2-isopropyl-5-methylcyclohexyloxy)carbonyl)acrylic acid；(Z)-4-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-4-oxobut-2-enoic acid
• CAS: 92419-65-3
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: GXEBTZBJBFEOQS-AFHYAWKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Maleinsaeure-mono-(1'R,3'R,4'S)-3-menthylester 在 lithium hydroxide 、 氯化二乙基铝 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 (2S,3S)-3-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxycarbonylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid
  参考文献：
  名称：

  Asymmetric Diels-Alder reaction. A facile route to chiral alkyl hydrogen cyclohexene-1,2-dicarboxylate

  摘要：

  DOI：

  10.1016/s0040-4039(01)81069-8
• 作为产物：
  描述：

  di-(-)-menthyl maleate 在 氢氧化钾 、 乙醇 作用下， 生成 Maleinsaeure-mono-(1'R,3'R,4'S)-3-menthylester
  参考文献：
  名称：

  Wassermann, Justus Liebigs Annalen der Chemie, 1931, vol. 488, p. 211,216, 234

  摘要：

  DOI：

文献信息

• Diastereoselectivities in the diels-alder reactions of cyclopentadiene with optically active dimenthyl fumarate and menthyl methyl fumarate in LiClO4/ether and on Al2O3
  作者：Satinder Bains、Richard M. Pagni、George W. Kabalka、Catherine Pala

  DOI：10.1016/s0957-4166(00)86236-9

  日期：1994.5

  Reactions of cyclopentadiene with (-)-dimenthyl fumarate, which yield adducts 1 and 2, and with (-)-menthyl methyl fumarate, which yield adducts 3 through 6, were carried out on alumina activated at different temperatures, in LiClO4/ether solutions, and in other media. Various diastereoselectivities - 2:1, 3:4, 6:5, endo:exo [(3+4):(5+6)], and % de [(3+6) - (4+5)]/[3+4+5+6] x 100] - were determined for these reactions. The LiClO4 data were analyzed using a model in which LiClO4 reversibly binds to the dienophile, resulting in competing catalyzed and uncatalyzed Diels-Alder reactions. Even in approximately 5 M LiClO4, there are sizable contributions from uncatalyzed reactions in all cases. Extrapolation of the data to infinite LiClO4, concentration yields data for the catalyzed reactions alone; only modest diastereoselectivities are seen for the catalyzed reactions. The alumina results were unusual because the endo:exo ratios of adducts were large but % de's were small. The selectivities on alumina could not be correlated to the activity of the solid. This behavior will occur when varying numbers and types of catalytic sites are exposed to the surface on activation.
• Wassermann, Justus Liebigs Annalen der Chemie, 1932, vol. 492, p. 266,274
  作者：Wassermann

  DOI：——

  日期：——
• WO2007/71085
  申请人：——

  公开号：——

  公开（公告）日：——
• Asymmetric Diels-Alder Reaction of Unsymmetrical Maleates. A Chemical Access to Chiral, Unsymmetrical cis-Cyclohexene-1,2-dicarboxylates
  作者：Keiji Maruoka、Matsujiro Akakura、Susumu Saito、Takashi Ooi、Hisashi Yamamoto

  DOI：10.1021/ja00093a013

  日期：1994.7

  A new route to optically active, unsymmetrical cis-cyclohexene-1,2-dicarboxylate derivatives has been developed on the basis of the asymmetric Diels-Alder reaction of chiral, unsymmetrical maleates catalyzed by certain Lewis acids. A notably high level of asymmetric induction has been observed in the asymmetric Diels-Alder reaction of unsymmetrical maleates possessing chiral auxiliaries such as alpha-phenethyl and trans-2-phenylcyclohexyl groups. The origin of the chiral outcome using these dienophiles has been elucidated.
• Korolew; Mur, Doklady Akademii Nauk SSSR, 1948, vol. 59, p. 251
  作者：Korolew、Mur

  DOI：——

  日期：——