(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate | 80868-49-1

• 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: (1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (1R,2R,4R)-bicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 80868-49-1
• 化学式: C₂₄H₃₂O₂
• 分子量: 352.517
• InChiKey: PHIGTPZTZFRCCX-UQYSYHQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (-)-8-phenylmenthyl acrylate 、 环戊二烯 、 四氯化钛 生成 (1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate
  参考文献：
  名称：

  OPPOLZER, W.;KURTH, M.;REICHLIN, D.;CHAPUIS, C.;MOHNHAUPT, M.;MOFFATT, F., HELV. CHIM. ACTA, 1981, 64, N 8, 2802-2807

  摘要：

  DOI：

文献信息

• A reinvestigation of asymmetric induction in diels-alder reactions to chiral acrylates.
  作者：Wolfgang Oppolzer、Mark Kurth、Daniel Reichlin、Frank Moffatt

  DOI：10.1016/s0040-4039(01)90516-7

  日期：1981.1

  The chiral induction in the Diels-Alder addition 1 → 2, assessed reliably by 19F-NMR-spectroscopy of the endo-esters 4, varied between 47 - 93% in favor of the 2-(R)-adducts 2 depending on the auxiliary chiral group and the Lewis-acid catalyst.

  的手性诱导的狄尔斯-阿德耳加成1→2，通过可靠地评估19所述的F-NMR光谱内切-酯4，47之间变化-赞成2-（R）93％2取决于-adducts辅助手性基团和路易斯酸催化剂。
• Asymmetric syntheses with a new optically active perhydronaphthalene based chiral auxiliary
  作者：David P.G. Hamon、Jeffrey W. Holman、Ralph A. Massy-Westropp

  DOI：10.1016/s0040-4020(01)80228-3

  日期：——

  (1R,4aS,8S,8aS)-8-(5′-Methoxy-2′-methylphenyl)-8-methyldecahydro-1-naphthalenol 3a is a highly efficient chiral auxiliary in the Diels-Alder addition of its acrylate ester 5 and in the DIBAL-H and Grignard reactions of its phenylglyoxylate ester 7.

  （1 R，4a S，8 S，8a S）-8-（5'-甲氧基-2'-甲基苯基）-8-甲基十氢-1-萘3a是Diels-Alder添加的高效手性助剂丙烯酸酯5以及在DIBAL-H和Grignard反应中的苯乙醛酸酯7。
• Fluorinated alcohols as solvents for diels-alder reactions of chiral acrylates
  作者：Curlos Cativiela、José I. García、José A. Mayoral、Ana.J. Royo、L. Salvatella

  DOI：10.1016/s0957-4166(00)80368-7

  日期：1993.7

  Fluorinated alcohols increase the rates and endo/exo selectivities of the Diels-Alder reactions of cyclopentadiene with (-)-menthyl and (-)-8-phenylmenthyl acrylates. The use of fluorinated alcohols also increases the diastereofacial selectivity in the reactions of (-)-menthyl acrylate, but decreases it when the dienophile is (-)-8-phenylmethyl acrylate. These facts are accounted for by the conformational preferences of the dienophile in non-HBD solvents and by the tendency of fluorinated alcohols to shift the conformational equilibrium towards the s-trans conformation.
• Preparation of 8-phenylmenthol and its diastereomer, 2-epi,ent-8-phenylmenthol. A caveat
  作者：James K. Whitesell、Chi Ling Liu、Charles M. Buchannan、Hwang Hsing Chen、Mark A. Minton

  DOI：10.1021/jo00354a032

  日期：1986.2
• AlPO4-Catalysed asymmetric Diels-Alder reactions of cyclopentadiene with chiral acrylates
  作者：Carlos Cativiela、José Ma Fraile、José I. García、José A. Mayoral、Juan M. Campelo、Diego Luna、José M. Marinas

  DOI：10.1016/s0957-4166(00)82230-2

  日期：——

  Reactions of cyclopentadiene with several chiral acrylates are studied and compared with the same reactions catalysed by Zn(II)-exchanged K10 montmorillonite. In general, amorphous AlPO4 is a more efficient catalyst than the clay. In particular, the reaction of cyclopentadiene with (-)-8-phenylmenthyl acrylate leads to 74% diastereomeric excess (d.e.) in methylene chloride at low temperatures. This result constitutes the highest asymmetric induction described to date for a solid-catalysed asymmetric Diels-Alder reaction. When the reactions are carried out in the absence of a solvent a noticeable decrease in selectivity is observed, probably due to an extensive competition of the non-catalysed reaction.