(1S,2R,5S)-Menthyl 2-oxo-phenylacetate | 67314-75-4

• 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: (1S,2R,5S)-Menthyl 2-oxo-phenylacetate
• 英文别名: [(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] 2-oxo-2-phenylacetate
• CAS: 67314-75-4
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: WBMULNOFMGKWPA-IMJJTQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  (1S,2R,5S)-Menthyl 2-oxo-phenylacetate 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl 2-diazo-2-phenylacetate
  参考文献：
  名称：

  Diastereoselectivity in the OH insertion reactions of rhodium carbenoids derived from phenyldiazoacetates of homochiral alcohols

  摘要：

  Rhodium(II) acetate catalysed decomposition of the phenyldiazoacetates 3 in the presence of alcohols (methanol, propan-2-ol, tert-butanol) led to the O-II insertion products 4-6 in varying yields; the diastercomeric excess of the product ranged from 5-53%.

  DOI：

  10.1016/s0040-4039(00)78227-x
• 作为产物：
  描述：

  D-薄荷醇 、 苯甲酰甲酸 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以96%的产率得到(1S,2R,5S)-Menthyl 2-oxo-phenylacetate
  参考文献：
  名称：

  Diastereoselectivity in the O-H Insertion Reactions of Rhodium Carbenoids Derived from Phenyldiazoacetates of Chiral Alcohols. Preparation of .alpha.-Hydroxy and .alpha.-Alkoxy Esters

  摘要：

  A series of phenyldiazoacetates 3 derived from enantiomerically pure alcohols ((-)-borneol, (+)menthol, (-)-menthol, (-)-8-phenylmenthol, (-)-trans-2-phenylcyclohexanol, (+)-trans-2-phenyl-cyclohexanol, and (-)10-(dicyclohexylsulfamoyl)-D-isoborneol) were prepared from the corresponding alpha-keto esters 1 by way of the tosylhydrazones 2. Rhodium(II)-catalyzed decomposition of the diazoacetates 3 in the presence of water or alcohols resulted in carbenoid O-H insertion reactions to give the corresponding 2-hydroxy- or 2-alkoxyphenylacetates in good yield, but with varying degrees of diastereoselectivity. A range of rhodium(II) and other metal catalysts were investigated, with rhodium(II) acetate and rhodium(II) acetamide giving the best results. The stereochemistry of the major diastereomer was proved in most cases by independent synthesis from a mandelic acid derivative of known configuration. Possible mechanisms are discussed.

  DOI：

  10.1021/jo00119a023

文献信息

• Chiral induction in photochemical reactions. 10. The principle of isoinversion: a model of stereoselection developed from the diastereoselectivity of the Paterno-Buechi reaction
  作者：Helmut Buschmann、Hans Dieter Scharf、Norbert Hoffmann、Martin Wolfgang Plath、Jan Runsink

  DOI：10.1021/ja00196a048

  日期：1989.7

  Reaction de benzeneglyoxylates chiraux avec des olefines cycliques du type furanne ou dioxole-1,3ine-4, pour former des oxetannes diastereoisomeres

  苯乙醛酸反应 chiraux avec des olenes cycliques du type furanne ou dioxole-1,3ine-4，浇注前脱氧杂环丁烷非对映异构体
• Photoredox-Catalyzed Radical–Radical Cross-Coupling of α-Ketoesters with Ethers: Access to Sterically Hindered α-Hydroxy Esters
  作者：Ming-Lin Yang、Zhi Guan、Yan-Hong He

  DOI：10.1021/acs.orglett.3c03403

  日期：2023.12.8

  We describe a photoredox catalysis method for synthesizing sterically hindered α-hydroxy esters from α-ketoesters and ethers through a radical–radical cross-coupling reaction. This approach utilizes commercially available Ir[dF(CF3)ppy]2(dtbbpy)PF6 as a photocatalyst and inexpensive and readily available nBu4NBr as a hydrogen atom transfer catalyst. Unactivated tetrahydrofuran and other ethers effectively

  我们描述了一种光氧化还原催化方法，通过自由基-自由基交叉偶联反应从 α-酮酯和醚合成空间位阻 α-羟基酯。该方法利用市售的Ir[dF(CF 3 )ppy] 2 (dtbbpy)PF 6作为光催化剂，并利用廉价且容易获得的n Bu 4 NBr作为氢原子转移催化剂。未活化的四氢呋喃和其他醚有效地与各种α-酮酯反应生成所需的产物。该反应的效率以其广泛的底物范围、良好的官能团耐受性和温和的反应条件而突出。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Comp.12, 1.4.1.1.1.5.2.1.7, page 69 - 97
  作者：

  DOI：——

  日期：——
• Rahm, A.; Pereyre, M., Bulletin des Societes Chimiques Belges, 1980, vol. 89, # 10, p. 843 - 848
  作者：Rahm, A.、Pereyre, M.

  DOI：——

  日期：——
• Nehrings, Alfred; Scharf, Hans-Dieter; Runsink, Jan, Angewandte Chemie, 1985, vol. 97, # 10, p. 882 - 883
  作者：Nehrings, Alfred、Scharf, Hans-Dieter、Runsink, Jan

  DOI：——

  日期：——