Dimethyl (1'S,2'S,5'R)-2-(2'-isopropenyl-5'-methylcyclohex-1'-yl)propane-1,3-dioate | 106431-82-7

• 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: Dimethyl (1'S,2'S,5'R)-2-(2'-isopropenyl-5'-methylcyclohex-1'-yl)propane-1,3-dioate
• 英文别名: dimethyl 2-[(1S,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexyl]propanedioate
• CAS: 106431-82-7
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: AHQWKJDVRCSTTJ-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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

• 作为产物：
  描述：

  methyl (5R)-2-(methoxycarbonyl)-5,9-dimethyldeca-2,8-dienoate 以 邻二氯苯 为溶剂， 反应 7.0h， 生成 dimethyl (1'R,2'R,5'R)-2-(2'-isopropenyl-5'-methylcyclohex-1'-yl)-propane-1,3-dioate 、 Dimethyl (1'S,2'S,5'R)-2-(2'-isopropenyl-5'-methylcyclohex-1'-yl)propane-1,3-dioate
  参考文献：
  名称：

  New and Efficient Lewis Acid Catalysts in Intramolecular Ene Reactions

  摘要：

  由香茅醛和丙二酸二甲酯进行的克诺文格尔加合物 3 的热或路易斯酸催化的分子内烯反应得到两种非对映异构体（5-甲基-2-反式-异丙烯基环己基）丙二酸二甲酯 4a 和 4b。事实证明，负载在碱性氧化铝上的无水氯化铁(III)是最好的催化剂，在 - 78°C 下，可以以 98.8:1.2 的比例生成两种非对映异构体 4a 和 4b，收率 92%。

  DOI：

  10.1055/s-1988-27573

文献信息

• Asymmetric induction in intramolecular ene reactions of 1,7-dienes
  作者：Lutz F Tietze、Uwe Beifuss

  DOI：10.1016/s0040-4039(00)84369-5

  日期：1986.1

  Lewis-acid catalyzed intramolecular ene reactions yielding trans-cyclohexanes 7a-d and 8a-d. The extent of diastereoselectivity depends on the reaction temperature. The 1,7-dienes 6 are obtained via Knoevenagel condensation of citronellal 5 with acyclic 1,3-dicarbonyls and analogous compounds 4. Starting with the diene 6e, however, an intramolecular hetero-Diels-Alder reaction takes place.

  1,7-二烯6a-d中的手性，双活化的亲和体发生热和路易斯酸催化的分子内烯反应，生成反式环己烷7a-d和8a-d。非对映选择性的程度取决于反应温度。1，7-二烯6是通过香茅醛5与无环的1，3-二羰基化合物和类似化合物4的Knoevenagel缩合获得的。然而，从二烯6e开始，发生分子内杂Diels-Alder反应。
• Surface-Mediated Reactions. 6. Effects of Silica Gel and Alumina on Acid-Catalyzed Reactions
  作者：Paul J. Kropp、Gary W. Breton、Stephen L. Craig、Scott D. Crawford、William F. Durland、John E. Jones、J. Scott Raleigh

  DOI：10.1021/jo00118a035

  日期：1995.6

  Adsorption of a variety of acids to chromatographic silica gel results in substantial enhancement of their catalytic activity-affording easily prepared, environmentally benign heterogeneous acids that are highly effective in mediating a number of processes. This was shown for the isomerization of allene 1 and dimerization of the corresponding 1,3-diene 2; cyclization of (R)-citronellal (5), the related diester 10, and 1,5-cyclooctadiene (15); Rupe rearrangement of alkynol 18; and Friedel-Crafts cyclodehydration of alcohols 21. By contrast, commercially available Nafion-H was significantly less effective as a heterogeneous acid catalyst. Chromatographic alumina displayed enigmatic behavior, showing enhanced acidity on the adsorption of HCl but little or no acidity on the adsorption of a variety of other types of acid. The results are discussed in terms of the surface structures of silica gel and alumina.
• Intramolecular ene reactions. 7. Asymmetric induction in intramolecular ene reactions of chiral 1,7-dienes: a diastereo- and enantioselective synthesis of substituted cyclohexanes
  作者：Lutz F. Tietze、Uwe Beifuss、Michael Ruther

  DOI：10.1021/jo00274a031

  日期：1989.6
• DIASTEREOSELECTIVE FORMATION OF trans-1,2-DISUBSTITUTED CYCLOHEXANES FROM ALKYLIDENEMALONATES BY AN INTRAMOLECULAR ENE REACTION: DIMETHYL (1'R,2'R,5'R)-2-(2'-ISOPROPENYL-5'-METHYLCYCLOHEX-1'-YL)-PROPANE-1,3-DIOATE
  作者：Tietze、Beifuss

  DOI：10.15227/orgsyn.071.0167

  日期：——
• Tietze, Lutz F.; Beifuss, Uwe; Antel, Jochen, Angewandte Chemie, 1988, vol. 100, # 5, p. 739 - 741
  作者：Tietze, Lutz F.、Beifuss, Uwe、Antel, Jochen、Sheldrick, George M.

  DOI：——

  日期：——