(5R)-5-methyl-2-(1-hydroxy-1-methylethyl)cyclohex-2-enone | 35736-66-4

• 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: (5R)-5-methyl-2-(1-hydroxy-1-methylethyl)cyclohex-2-enone
• 英文别名: 5-methyl-2-(1-hydroxy-1-methylethyl)-2-cyclohexene-1-one；(-)-(1R)-8-Hydroxy-Δ⁴⁽⁵⁾-p-menthen-3-on；(-)-8-Hydroxy-Δ⁴-p-menthen-3-on；2-Cyclohexen-1-one, 2-(1-hydroxy-1-methylethyl)-5-methyl-, (5R)-；(5R)-2-(2-hydroxypropan-2-yl)-5-methylcyclohex-2-en-1-one
• CAS: 35736-66-4
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: SNBPZAIQWQXUCR-SSDOTTSWSA-N

物化性质

• 沸点：
  284.5±19.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)
• 保留指数：
  1264

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (5R)-5-methyl-2-(1-hydroxy-1-methylethyl)cyclohex-2-enone 在 lithium aluminium tetrahydride 作用下， 生成 (-)-(1R,3R)-Δ⁴⁽⁵⁾-p-Menthen-3,8-diol (4)
  参考文献：
  名称：

  （-）-顺式-薄荷酚和（+）-普莱贡的染料敏化光氧合。用于添加的O- 2（1 Δ克）与烯丙基键双键。羟基或羰基†

  摘要：

  （-）-顺式-Pulegol（1）和（+）-pulegone（2）易于在溶液中进行染料敏化的光氧合时添加一摩尔的氧，几乎仅形成烯丙基氢过氧化物。

  DOI：

  10.1002/hlca.19710540714
• 作为产物：
  描述：

  (R)-3,3,6-Trimethyl-3,5,6,7-tetrahydro-benzo[1,2]dioxol-7a-ol 在 三苯基膦 作用下， 生成 (5R)-5-methyl-2-(1-hydroxy-1-methylethyl)cyclohex-2-enone
  参考文献：
  名称：

  Reaction of singlet oxygen with .alpha.,.beta.-unsaturated ketones and lactones

  摘要：

  DOI：

  10.1021/ja00528a053

文献信息

• Efficient Photooxygenation of Olefins by a C₆₀Derivative Bearing an Organofluorine Tail
  作者：Hideo Nagashima、Koji Hosoda、Tomoaki Abe、Shoichi Iwamatsu、Takaaki Sonoda

  DOI：10.1246/cl.1999.469

  日期：1999.6

  A C60 derivative bearing an organofluorine tail through the dimethylsilyl moiety (1) was proved to be an efficient photosensitizer in C6F6. Photooxygenation of olefins or dienes was accomplished by catalysis of 1 (0.5–1.5 mol%) at room temperature under an oxygen atmosphere.

  一种通过二甲基硅基部分连接有有机氟尾的C60衍生物（1）被证明在C6F6中是一种高效的光敏剂。在常温下，在氧气氛围下，1以0.5–1.5 mol%的催化剂成功实现了烯烃或二烯的光氧化反应。
• Biotransformation of terpenic compounds by fungi I. Metabolism of R-(+)-pulegone
  作者：Mustapha Ismaili-Alaoui、Bachier Benjilali、Didier Buisson、Robert Azerad

  DOI：10.1016/s0040-4039(00)74208-0

  日期：1992.4

  R-(+)-Pulegone 1 is converted by several fungal strains to new regioselectively hydroxylated compounds. Epoxidation of the double bond does not seem to be responsible for the main observed hydroxylation pattern.

  R-（+）-Pulegone 1通过几种真菌菌株转化为新的区域选择性羟基化化合物。双键的环氧化似乎与观察到的主要羟基化模式无关。
• Transformation of a Monoterpene Ketone, (<i>R</i>)-(+)-Pulegone, a Potent Hepatotoxin, in <i>Mucor </i><i>piriformis</i>
  作者：K. M. Madyastha、H. V. Thulasiram

  DOI：10.1021/jf980164n

  日期：1999.3.1

  using a fungal strain, Mucor piriformis. Eight metabolites, namely, 5-hydroxypulegone (II), piperitenone (III), 6-hydroxypulegone (IV), 3-hydroxypulegone (V), 5-methyl-2-(1-hydroxy-1-methylethyl)-2-cyclohexene-1-one (VI), 3-hydroxyisopulegone (VII), 7-hydroxypiperitenone (VIII), and 7-hydroxypulegone (IX), have been isolated from the fermentation medium and identified. GC analysis of the metabolites indicated

  使用真菌菌株梨形毛霉菌（Mucor piriformis）研究了单萜酮（R）-（+）-pulegone（I）（一种有效的肝毒素）的生物转化。八种代谢物，分别是5-羟基普勒酮（II），哌啶酮（III），6-羟基普勒酮（IV），3-羟基普勒酮（V），5-甲基-2-（1-羟基-1-甲基乙基）-2-环己烯从发酵培养基中分离并鉴定了-1-酮（VI），3-羟基异戊烯酮（VII），7-羟基哌啶酮（VIII）和7-羟基Pulegone（IX）。代谢物的GC分析表明，II是形成的主要代谢物。生物体通过C-5位置的羟基化或环亚甲基的羟基化来引发转化，前者是主要活性。在鉴定代谢物的基础上，已经提出了（R）-（+）-普勒高酮的生物转化途径。该生物体转化（S）-（-）-pulegone的方式与它的（R）-（+）-对映体的转化方式相似。当异普勒酮（X）用作底物时，生物体将其异构化为普勒酮（I），然后转化为代谢产物II-IX。
• Synthetic Chemistry with Fullerenes. Photooxygenation of Olefins
  作者：Hidetoshi Tokuyama、Eiichi Nakamura

  DOI：10.1021/jo00084a036

  日期：1994.3

  Under irradiation with visible or UV (>290 nm) light in the presence of molecular oxygen and a minute amount of fullerenes, olefins and dienes undergo ene and Diels-Alder reactions with singlet oxygen to give photooxygenation products. The regio- and stereoselectivities of the photooxygenation of beta-myrcene, (+)-pulegone, 4-methylpent-3-en-2-ol, and (+)-limonene were very similar to those observed in known singlet oxygen reactions, indicating that the fullerene-sensitized reaction generates free singlet oxygen. The efficiency of fullerenes and conventional sensitizers was qualitatively examined by using the Diels-Alder reaction between O-1(2) and furan-2-carboxylic acid as a probe. Among those examined, C-70 was found to be the most effective. The reaction was the fastest and completed with as little as 0.0001 equiv of C-70. C-60 and hematoporphyrin were found to be of similar efficiency. The methanofullerene 13, which lacks one olefinic conjugation in the C-60 core, was as good as C60 itself, but the aminofullerene 14, lacking six double bonds, was quite inferior. The fullerene carboxylic acid 15, which was previously shown to show considerable biochemical activity, was found to be capable of generating singlet oxygen in aqueous DMSO.
• Williams, Howard J.; Moyna, Guillermo; Scott, A. Ian, Journal of the Indian Chemical Society, 1998, vol. 75, # 10-12, p. 838 - 840
  作者：Williams, Howard J.、Moyna, Guillermo、Scott, A. Ian、Hamada, Hiroki、Lwin, War War、Tanaka, Toshinori、Furuya, Tsutomu

  DOI：——

  日期：——