hydroxy-(2-oxo-cyclohexyl)-acetic acid | 98558-76-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: hydroxy-(2-oxo-cyclohexyl)-acetic acid
• 英文别名: Hydroxy-(2-oxo-cyclohexyl)-essigsaeure；2-hydroxy-2-(2-oxocyclohexyl)acetic acid
• CAS: 98558-76-0
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: DCUDYXKQZWYTED-UHFFFAOYSA-N

物化性质

• 沸点：
  389.6±12.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  hydroxy-(2-oxo-cyclohexyl)-acetic acid 在 一水合肼 作用下， 反应 1.0h， 生成 5,6,7,8-四氢-2H-噌啉-3-酮
  参考文献：
  名称：

  Suzuki, Koichi; Senoh, Akihiro; Ueno, Kazunori, Heterocycles, 2002, vol. 57, # 4, p. 723 - 731

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 hydroxy-(2-oxo-cyclohexyl)-acetic acid
  参考文献：
  名称：

  Synthesen in der Reihe der Anthelmintika. II. Mitteilung

  摘要：

  DOI：

  10.1002/ardp.19542870806

文献信息

• 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。
• Indium trichloride catalysed Mukaiyama aldol reaction in water
  作者：Teck-Peng Loh、Jian Pei、Guo-Qiang Cao

  DOI：10.1039/cc9960001819

  日期：——

  In the presence of a catalytic amount of indium(III) chloride (InCl3)(20 mol%), aldehydes react smoothly with ketone trimethylsilyl enol ethers in water to afford the corresponding aldol adducts in good yields.

  在氯化铟(III)（InCl3）（20 mol%）的催化作用下，醛与酮的甲硅烷基烯醇醚在水中的反应能够顺利进行，以良好的产率得到相应的醇醛加成产物。
• Method for the production of 2-coumarone and substituted 2-coumarones
  申请人：——

  公开号：US20030171601A1

  公开（公告）日：2003-09-11

  The invention relates to a method for the production of 2-coumarone or substituted 2-coumarones, whereby cyclohexanone or substituted cyclohexanone is reacted with a carboxyl-containing acylating agent a) to give methyl 2-(2-oxo-cyclohexyl)-2-hydroxyacetate or substituted methyl 2-(2-oxo-cyclohexyl)-2-hydroxyacetates, which are either a 1 ) directly converted to 2-coumarone or substituted 2-coumarones by means of catalytic gas-phase dehydrogenation, or a 2 ) dehydrated by means of azeotropic distillation under basic conditions, or by use of a strong acid, or a strongly acidic ion exchanger to a mixture of methyl 2-oxocyclohexylidenacetate and the enol-lactone of the 2-oxocyclohexylidenacetic acid, or a mixture of substituted methyl 2-oxocyclohexylidenacetate and the enol-lactone of the substituted 2-oxocyclohexylidenacetic acid, which is finally converted in turn by catalytic gas-phase dehydrogenation to 2-coumarone, or substituted 2-coumarones, or b) are directly converted under acidic or basic conditions into a mixture of methyl 2-oxocyclohexylidenacetate and the enol-lactone of 2-oxo-cyclohexylidenacetic acid, or a mixture of substituted methyl 2-oxocyclohexylidenacetate and the enol-lactone of the substituted 2-oxo-cyclohexylidenacetic acid, which is finally converted in turn by catalytic gas-phase dehydrogenation into 2-coumarone or substituted 2-coumarones.

  该发明涉及一种生产2-香豆酮或取代2-香豆酮的方法，其中环己酮或取代环己酮与含羧基的酰化试剂a) 反应，得到甲基2-(2-氧代环己基)-2-羟基乙酸酯或取代甲基2-(2-氧代环己基)-2-羟基乙酸酯，这些化合物要么a1) 直接通过催化气相脱氢转化为2-香豆酮或取代2-香豆酮，要么a2) 在碱性条件下通过共沸蒸馏脱水，或使用强酸，或强酸性离子交换剂将其转化为甲基2-氧代环己基亚乙酸酯和2-氧代环己基亚乙酸的烯醇内酯的混合物，或取代甲基2-氧代环己基亚乙酸酯和取代2-氧代环己基亚乙酸的烯醇内酯的混合物，最终再通过催化气相脱氢转化为2-香豆酮或取代2-香豆酮，或b) 直接在酸性或碱性条件下转化为甲基2-氧代环己基亚乙酸酯和2-氧代环己基亚乙酸的烯醇内酯的混合物，或取代甲基2-氧代环己基亚乙酸酯和取代2-氧代环己基亚乙酸的烯醇内酯的混合物，最终再通过催化气相脱氢转化为2-香豆酮或取代2-香豆酮。
• Aqueous organocatalyzed aldol reaction of glyoxylic acid for the enantioselective synthesis of α-hydroxy-γ-keto acids
  作者：Fernando J. N. Moles、Gabriela Guillena、Carmen Nájera

  DOI：10.1039/c3ra46800c

  日期：——

  N-Tosyl-(Sa)-binam-L-prolinamide is an efficient catalyst for the aqueous aldol reaction, between glyoxylic acid, as monohydrate or aqueous solution, and ketones. This reaction led to the formation of chiral α-hydroxy-γ-keto carboxylic acids in high levels of diastereo- and enantioselectivities achieving mainly anti aldol products.

  N-甲苯磺酰基-（S a）-联氨-L-脯氨酰胺是用于乙醛酸（作为一水合物或水溶液）与酮之间的水性羟醛反应的有效催化剂。该反应导致以高水平的非对映体和对映体选择性形成手性α-羟基-γ-酮基羧酸，主要获得抗羟醛产物。
• US6858743B2
  申请人：——

  公开号：US6858743B2

  公开（公告）日：2005-02-22