Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester | 88002-15-7

• 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: Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester
• 英文别名: (1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl 2-oxophenylacetate；(-)-(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl phenylglyoxalate；(-)-(1R,2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexyl-phenylglyoxylat；(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 2-oxo-2-phenylacetate；(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl benzoylformate；Phenylglyoxylsaeure-(1R,3R,4S)-(-)-8-phenylmenthylester；(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl oxo(phenyl)acetate；[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-oxo-2-phenylacetate
• CAS: 88002-15-7
• 化学式: C₂₄H₂₈O₃
• 分子量: 364.485
• InChiKey: YWVKGFDQNCBLNH-DUXKGJEZSA-N

物化性质

• 沸点：
  472.7±14.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester 在 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 5.5h， 生成 (S)-2-苯基-1-丙醇
  参考文献：
  名称：

  Stereogenic reactions of the α-carbon radicals of 8-phenylmenthyl esters

  摘要：

  描述了 8-苯基苯甲酯的立体选择性自由基还原和环化过程；主要产物被认为来自于具有与酯的烷氧基对立的较大取代基构象的过渡态。

  DOI：

  10.1039/c39910001603
• 作为产物：
  描述：

  (1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 苯 为溶剂， 生成 Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester
  参考文献：
  名称：

  Diastereoselective reduction of an α-keto-ester derived from (−)-8-phenylmenthol: A 4-step synthesis of R-Halostachine analogue.

  摘要：

  An efficient (80% total yield) 4-step synthesis of a 94% e.e. R-(-)-Halostachine analogue is described. The method offers the possibility to introduce various substituents onto the aromatic ring and various alkyl groups on the amine. A one-step and high yield (almost-equal-to 100%) conversion of esters into amides is presented.

  DOI：

  10.1016/s0957-4166(00)82014-5

文献信息

• Selective Formation of Functionalized α-Quaternary Malononitriles toward 5,5-Disubstituted Pyrrolopyrimidinones
  作者：Alan Whitehead、Yong Zhang、Jamie McCabe Dunn、Edward C. Sherer、Yu-hong Lam、John Stelmach、Aaron Sun、Melisa Shiroda、Robert K. Orr、Sherman T. Waddell、Subharekha Raghavan

  DOI：10.1021/acs.orglett.7b01930

  日期：2017.9.1

  A modular, selective approach to complex α-tertiary substituted malononitriles is reported. The method takes advantage of β-ester-substituted α,α-dinitrile alkenes as highly reactive, chemoselective electrophiles for 1,4-additions with organometallic nucleophiles to produce functionally and sterically dense all-carbon quaternary centers. In the presence of a chiral ester auxiliary bearing an aromatic

  报道了一种复杂的α-叔取代丙二腈的模块化，选择性方法。该方法利用β-酯取代的α，α-二不饱和烯烃作为有机金属亲核试剂进行1,4-加成的高反应性，化学选择性亲电试剂，可产生功能上和空间上均密集的全碳四元中心。在带有芳香环的手性酯助剂的存在下，由于有利的阳离子-π相互作用，发生了1,4-加成，选择性好至极好。高度官能化的丙二腈代表了多种构建基块，可用于高效，高度选择性的5,5-二取代吡咯并嘧啶酮的合成。
• Asymmetric synthesis of benzilic acid analogues using 8-phenylmenthol as a chiral auxiliary
  作者：Dale O. Kiesewetter

  DOI：10.1016/s0957-4166(00)80069-5

  日期：1993.10

  ligands required the preparation of chiral fluoroalkyl benzilic acids. An enantioselective synthesis of substituted benzilic acids was achieved using 8-phenylmenthol as the chiral auxiliary. Grignard addition to the si face of 8-phenylmenthyl benzoylformate 7 proceeded with high selectivity. The results of the chiral induction support assignments of the chirality of benzilic acids previously resolved

  我们合成18 F-标记的毒蕈碱受体配体的程序需要制备手性氟烷基苯甲酸。使用8-苯基薄荷醇作为手性助剂，实现了对取代苯甲酸的对映选择性合成。在8-苯基薄荷基苯甲酰基甲酸酯7的si表面上进行格氏试剂以高选择性进行。手性诱导的结果支持先前通过结晶拆分的苯甲酸的手性分配。该方法用于合成（R）-奎宁环烷基-（R）-（4-碘）苯甲酸酯，事实证明与真实样品相同。另外，该方法允许以立体选择性的方式制备（R）-和（S）-氟乙基苯甲酸。
• Investigation of chiral induction in photochemical oxetane formation
  作者：H. Koch、J. Runsink、H.-D. Scharft

  DOI：10.1016/s0040-4039(00)88139-3

  日期：1983.1

  The formation of oxetanes from photochemical addition of tetramethylethylene (TME) or diethylketeneacetal with phenylglyoxylic acid esters in the “concave” position leads to high diastereomeric excess (de).

  在“凹”位置通过光化学加成四甲基乙烯（TME）或二乙基酮缩醛与苯乙醛酸酯形成氧杂环丁烷会导致很高的非对映异构体过量（d e）。
• Asymmetric induction. Reduction, nucleophilic addition to, and ene reactions of chiral α-ketoesters
  作者：James K. Whitesell、Don Deyo、Apurba Bhattacharya

  DOI：10.1039/c39830000802

  日期：——

  Ketoesters of 8-phenylmenthol undergo reduction with potassium tri-isopropoxyborohydride, addition of Grignard reagents, and ene reactions with asymmetric induction levels of 90% and above.

  用三异丙氧基硼氢化钾还原8-苯基薄荷醇的酮酸酯，添加格氏试剂，以及不对称诱导水平达90％或更高的烯类反应。
• 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。