(1R,4R)-(-)-4-hydroxy-p-menth-3-one | 7599-80-6

• 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: (1R,4R)-(-)-4-hydroxy-p-menth-3-one
• 英文别名: (1R,4R)-4-hydroxy-p-menthan-3-one；(1R,4R)-4-hydroxy-p-menth-3-one；(2R,5R)-2-hydroxymenthone；(1R,4R)-(-)-4-Hydroxy-menthon；(-)-4-Hydroxy-menthon；(2R,5R)-2-hydroxy-5-methyl-2-propan-2-ylcyclohexan-1-one
• CAS: 7599-80-6；55102-25-5；55122-53-7；74219-28-6；96554-79-9；7616-79-7
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: FIPCVTLYVPYVMZ-PSASIEDQSA-N

物化性质

• 沸点：
  107-109 °C(Press: 16 Torr)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,4R)-(-)-4-hydroxy-p-menth-3-one 在 lithium aluminium tetrahydride 作用下， 生成 4β-hydroxy-l-menthol
  参考文献：
  名称：

  Stereochemical studies of monoterpene compounds. II. The conformation of 4-hydroxymenthones

  摘要：

  DOI：

  10.1021/jo01279a026
• 作为产物：
  描述：

  (-)-薄荷酮 生成 (1R,4R)-(-)-4-hydroxy-p-menth-3-one
  参考文献：
  名称：

  HAMADA, HIROKI, BULL. CHEM. SOC. JAP., 61,(1988) N 3, 869-878

  摘要：

  DOI：

文献信息

• Enantioselectivity in the Biotransformation of Mono- and Bicyclic Monoterpenoids with the Cultured Cells of<i>Nicotiana tabacum</i>
  作者：Hiroki Hamada

  DOI：10.1246/bcsj.61.869

  日期：1988.3

  The biotransformation of the enantiomeric pairs of p-menthane and bicyclo[2.2.1] and [3.1.1]heptane derivatives with the cultured cells of Nicotiana tabacum was investigated. It was found that (i) the cultured cells discriminate the enantiomers of p-menthan-2-ol and bicyclo[2.2.1]heptan-2-ol and bicyclo[3.1.1]heptan-3-ol derivatives, and enantioselectively convert these alcohols to the corresponding

  研究了对薄荷烷和双环 [2.2.1] 和 [3.1.1] 庚烷衍生物的对映体对与烟草培养细胞的生物转化。发现(i)培养的细胞区分对-薄荷醇-2-醇和双环[2.2.1]庚烷-2-醇和双环[3.1.1]庚烷-3-醇衍生物的对映异构体，并对映选择性转化将这些醇转化为相应的酮，(ii) 细胞高度还原 p-menthan-2-one 衍生物的羰基，但不还原 p-menthan-3-ones 的羰基，以及 (iii) 细胞区分双环[3.1.1]hept-2-en-4-one（verbenone）的对映异构体，并对映选择性还原（1S，5S）-对映异构体的C-C双键。
• Oxidation of Alcohols with<i>t</i>-Butyl Chromate. III. The Oxidation of Alicyclic Alcohols
  作者：Takayuki Suga、Tamon Matsuura

  DOI：10.1246/bcsj.38.1503

  日期：1965.9

  1) The t-butyl chromate oxidation of myrtenol gave no ester, but it did give the corresponding aldehyde as the main product, while the oxidation of cyclohexylcarbinol gave a mixture of the corresponding aldehyde, acid and ester in comparable yields. 2) A similar oxidation of cyclohexanol afforded the corresponding ketone in a high yield, while the oxidation of cyclohexane-trans-1,2-diol produced no

  1) 桃金娘醇的铬酸叔丁酯氧化没有产生酯，但它确实产生了相应的醛作为主要产物，而环己基甲醇的氧化产生了相应的醛、酸和酯的混合物，产率相当。2）环己醇的类似氧化以高产率提供相应的酮，而环己烷-反式-1,2-二醇的氧化不产生相应的二酮，但确实产生了乙二醇裂变产物和环酯，如反式- 1,2-己二氧基环己烷（一种新化合物）。另一方面，对薄荷烷-反式-3,4-二醇仅以良好的产率产生相应的羟基酮。
• Silica-Catalysed and Highly Stereoselective Convergent and Nonconvergent Rearrangements of Menthone Enol Acetate Epoxides: Easy Access to the Four α-Hydroxymenthone Stereoisomers
  作者：Sylvain Tranchimand、Bruno Faure、Jean-Valère Naubron、Véronique Alphand、Alain Archelas、Gilles Iacazio

  DOI：10.1002/ejoc.201200414

  日期：2012.8

  to the biocatalytic access of structurally useful α-hydroxy ketones, we made the unexpected observation that epoxy enol acetates derived from (+)- and (–)-menthone stereoselectively rearranged on exposure to silica through a diastereoselective process, providing easy access to the complete set of α-hydroxymenthone stereoisomers. The absolute configurations of the four stereoisomers were unambiguously

  在一个致力于生物催化获取结构上有用的 α-羟基酮的项目中，我们意外地观察到，衍生自 (+)- 和 (-)-薄荷酮的环氧烯醇乙酸酯通过非对映选择性过程暴露于二氧化硅后立体选择性重排，提供了简单的获取完整的 α-羟基薄荷酮立体异构体。通过 IR-VCD 和 X 射线衍射明确确定了四种立体异构体的绝对构型，从而澄清了一些文献差异。四种立体异构体中的两种也可以通过对映会聚过程获得，从而避免了此类非对映选择性反应固有的 50% 产率限制。还描述了允许极快反应 (< 2 h) 的无溶剂版本。最后，
• Biotransformation of 3-oxo-p-menthane derivatives by cultured cells of Nicotiana tabacum
  作者：Takayuki Suga、Toshifumi Hirata、Hiroki Hamada、Satoru Murakami

  DOI：10.1016/0031-9422(88)80269-3

  日期：——

  Abstract The biotransformation of (1R)-(+)-p-menth-4(8)-en-3-one and (1R,4S)-(−)- and (1R,4R)-(+)-p-menth-3-ones with a suspension of cultured cells of Nicotiana tabacum was investigated. It was found that (i) the cultured cells regio- and stereoselectively hydroxylated the 4-position of (1R,4S)- and (1R,4R)-p-menth-3-ones to give (1R,4R)- and (1R,4S)-4-hydroxy-p-menth-3-ones, respectively and (ii)

  摘要 (1R)-(+)-p-menth-4(8)-en-3-one 和 (1R,4S)-(-)- 和 (1R,4R)-(+)-p- 的生物转化研究了含有烟草培养细胞悬浮液的薄荷 3-ones。发现 (i) 培养的细胞区域和立体选择性羟基化 (1R,4S)- 和 (1R,4R)-p-menth-3-ones 的 4-位，得到 (1R,4R)- 和 ( 1R,4S)-4-hydroxy-p-menth-3-ones 和 (ii) 培养的细胞立体选择性地减少了来自 si 的 p-menth-4(8)-en-3-one 的 CC 双键-face 位于 C-4 处，然后是来自 re-face 的羰基。
• Stereoselectivity in Oxidative and Reductive Transformations of<i>p</i>-Menthane Derivatives with the Cultured Cells of<i>Nicotiana tabacum</i>
  作者：Takayuki Suga、Hiroki Hamada、Toshifumi Hirata、Shunsuke Izumi

  DOI：10.1246/cl.1987.903

  日期：1987.5.5

  The biotransformation of the enantiomeric pairs of 2- and 3-oxygenated p-menthane derivatives with the cultured cells of Nicotiana tabacum was investigated. It was found that (i) the cultured cells transform only 2-oxygenated p-menthane derivatives to a great extent, (ii) the cultured cells cause the highly stereospecific reduction for (1R,4R)-2-oxo-p-menthane, whereas this is not the case for its

  研究了 2-和 3-氧化对薄荷烷衍生物的对映体对与烟草培养细胞的生物转化。发现 (i) 培养细胞仅在很大程度上转化 2-氧化对薄荷烷衍生物，(ii) 培养细胞导致 (1R,4R)-2-oxo-p-menthane 的高度立体定向还原，而它的对映异构体并非如此，并且 (iii) 培养的细胞对映选择性氧化 2-羟基-p-薄荷烷的羟基。