(-)-8-Phenylmenthyl glyoxylate hydrate | 108794-12-3

• 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: (-)-8-Phenylmenthyl glyoxylate hydrate
• 英文别名: Acetic acid, dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester；[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2,2-dihydroxyacetate
• CAS: 108794-12-3
• 化学式: C₁₈H₂₆O₄
• 分子量: 306.402
• InChiKey: ARNALRSJBJGILK-BPLDGKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-8-Phenylmenthyl glyoxylate hydrate 以89%的产率得到
  参考文献：
  名称：

  WHITESELL J. K.; BHATTACHARYA A.; BUCHANAN C. M.; CHEN H. H.; DEYO D.; JA+, TETRAHEDRON, 42,(1986) N 11, 2993-3001

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate 生成 (-)-8-Phenylmenthyl glyoxylate hydrate
  参考文献：
  名称：

  WHITESELL J. K.; BHATTACHARYA A.; BUCHANAN C. M.; CHEN H. H.; DEYO D.; JA+, TETRAHEDRON, 42,(1986) N 11, 2993-3001

  摘要：

  DOI：

文献信息

• Trifluoromethane sulphonic acid: a Brönsted acid catalyst for the addition of allyltributylstannanes to carbonyl compounds in water
  作者：Teck-Peng Loh、Jia Xu

  DOI：10.1016/s0040-4039(99)00122-7

  日期：1999.3

  Trifluoromethane sulphonic acid catalyses the addition of allyltributylstannane to carbonyl compounds in water to give the corresponding homoallylic alcohols in high yields.

  三氟甲烷磺酸催化将烯丙基三丁基锡烷加到水中的羰基化合物中，从而以高收率得到相应的均烯丙基醇。
• InCl3-Catalyzed direct aldol reactions of glyoxylic acid monohydrate and glyoxylates with various ketones: scope and limitations
  作者：Teck-Peng Loh、Li-Chun Feng、Lin-Li Wei

  DOI：10.1016/s0040-4020(01)00309-x

  日期：2001.5

  The direct aldol reactions of various ketones with glyoxylic acid and glyoxylates afforded the α-hydroxy acid and α-hydroxy esters in good yields and high regioselectivities.

  各种酮与乙醛酸和乙醛酸酯的直接醛醇缩合反应以良好的产率和高的区域选择性提供了α-羟基酸和α-羟基酯。
• Highly diastereoselective synthesis of 2-azabicyclo[2.2.1]hept-5-ene derivatives: Bronsted acid catalyzed aza-Diels–Alder reaction between cyclopentadiene and imino-acetates with two chiral auxiliaries
  作者：Xerardo García-Mera、José E. Rodríguez-Borges、M. Luísa C. Vale、Maria J. Alves

  DOI：10.1016/j.tet.2011.06.097

  日期：2011.9

  The cycloaddition between protonated glyoxylate imines possessing two chiral auxiliaries, N-(S)- or N-(R)-1-phenylethyl and (−)-8-phenylmenthyl or (+)-8-phenylneomenthyl, and cyclopentadiene is described. The absolute configuration of all adducts formed was unequivocally assigned through NMR, specific optical rotation, and X-ray data of appropriated derivatives. Experimental results confirm the highly

  描述了具有两个手性助剂N-（S）-或N-（R）-1-苯基乙基和（-）-8-苯基薄荷基或（+）-8-苯基新薄荷基的质子化乙醛酸亚胺与环戊二烯之间的环加成。通过NMR，比旋光度和适当衍生物的X射线数据明确分配了所有形成的加合物的绝对构型。实验结果证实了高度外切（ -这些氮杂狄尔斯-阿尔德反应-选择性，被从（下午8点）的组合获得的单加合物- [R -PEA）和（8PNM） - （小号-PEA）。
• An Efficient Method for Preparation of Chiral Arylmenthol Glyoxylates
  作者：José M. Blanco、Olga Caamaño、Franco Fernández、Xerardo García-Mera、Carmen López、José E. Rodríguez-Borges、Antonio R. Hergueta

  DOI：10.1055/s-1998-2198

  日期：1998.11

  Glyoxylates of three chiral alcohols were conveniently prepared by reaction of the alcohol with oxalyl chloride followed by reduction of the resulting alkoxy oxalyl chloride with tributyltin hydride. The products were isolated in 75–80% yield by straightforward flash chromatography.

  先将三种手性醇与草酰氯反应，然后用氢化三丁基锡还原生成的草酰氯烷氧基，这样就能方便地制备三种手性醇的乙醛酸乙二酯。通过直接的闪速色谱法，可分离出产率为 75-80% 的产品。
• Rhodium-catalyzed reactions of arylbismuth and aryllead reagents with a chiral glyoxylate hydrate in air and water: water-promoted diastereoselectivity enhancement
  作者：Rui Ding、Cheng-Sheng Ge、Yong-Jun Chen、Dong Wang、Chao-Jun Li

  DOI：10.1016/s0040-4039(02)01814-2

  日期：2002.10

  In the presence of a rhodium catalyst, a chiral glyoxylate hydrate reacts with arylbismuth and aryllead reagents in water and under an atmosphere of air to give the corresponding addition products in high yields. The diastereoselectivities of the reactions were dramatically improved by using water as the solvent. (C) 2002 Elsevier Science Ltd. All rights reserved.