(-)-menthyl methyl fumarate | 76529-73-2

• 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: (-)-menthyl methyl fumarate
• 英文别名: methyl l-menthyl fumarate；methyl-((1R)-menthyl)-fumarate；Fumarsaeure-methylester-((1R)-menthylester)；Methyl-((1R)-menthyl)-fumarat；1-O-methyl 4-O-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (E)-but-2-enedioate
• CAS: 76529-73-2
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: MSIRNWPCRNKGFL-SDEBKXSHSA-N

物化性质

• 沸点：
  120 °C(Press: 0.5 Torr)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  (-)-menthyl methyl fumarate 在 sodium hydroxide 作用下， 以 苯 为溶剂， 生成 2',3'-dimethoxycarbonylspirofluorenecyclopropene
  参考文献：
  名称：

  重氮芴与丙烯酸薄荷酯或 8-苯基薄荷酯和富马酸酯衍生物在 1,3-偶极环加成反应中的不对称诱导

  摘要：

  发现通过使用 Corey 的 8-苯基薄荷基作为这些酯中的手性 O-烷基，重氮芴与手性丙烯酸酯或富马酸酯衍生物的 1,3-偶极环加成反应的光学产率显着提高。所得环丙烷的绝对立体化学与 Walborsky 等人提出的“重氮交换”机制所预期的不同。

  DOI：

  10.1246/cl.1987.93
• 作为产物：
  描述：

  Maleinsaeure-mono-(1'R,3'R,4'S)-3-menthylester 在 溴 作用下， 以 四氯化碳 、 乙醚 为溶剂， 生成 (-)-menthyl methyl fumarate
  参考文献：
  名称：

  Diastereoselectivities in the diels-alder reactions of cyclopentadiene with optically active dimenthyl fumarate and menthyl methyl fumarate in LiClO4/ether and on Al2O3

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)86236-9

文献信息

• Transition states in catalyzed and uncatalyzed Diels-Alder reactions. Cooperativity as a probe of geometry
  作者：Laren M. Tolbert、Mahfuza B. Ali

  DOI：10.1021/ja00325a016

  日期：1984.6

  Le role des acides de Lewis dans l'augmentation de l'induction asymetrique est d'accroitre l'interaction sterique a un bout du dienophile

  Le role des acides de Lewis dans l'augmentation de l'induction asymetrique est d'accroitre l'interaction sterique a un bout du dienophile
• A simple, powerful, and efficient method for transesterification
  作者：Otto Meth-Cohn

  DOI：10.1039/c39860000695

  日期：——

  Aromatic and α,β-unsaturated methyl esters undergo efficient transesterification at ambient temperature or below with primary, secondary, or (particularly) tertiary alcohols in the presence of butyl-lithium in tetrahydrofuran solution.

  在丁基锂存在下于四氢呋喃溶液中，在环境温度以下，芳族和α，β-不饱和甲酯与伯，仲或（尤其是）叔醇进行有效的酯交换反应。
• Wassermann, Justus Liebigs Annalen der Chemie, 1931, vol. 488, p. 211,216, 234
  作者：Wassermann

  DOI：——

  日期：——
• Asymmetric Diels-Alder reaction. A facile route to chiral alkyl hydrogen cyclohexene-1,2-dicarboxylate
  作者：Kyoji Furuta、Shigeo Hayashi、Yoshikazu Miwa、Hisashi Yamamoto

  DOI：10.1016/s0040-4039(01)81069-8

  日期：1987.1
• METH-COHN, OTTO, J. CHEM. SOC. CHEM. COMMUN., 1986, N 9, 695-697
  作者：METH-COHN, OTTO

  DOI：——

  日期：——