p-Menthadiene<1(7),8>-cis-ol-(2) | 10374-04-6

• 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: p-Menthadiene<1(7),8>-cis-ol-(2)
• 英文别名: cis-2-methylene-5-isopropenylcyclohexanol；(2R,4R)-p-mentha-[1(7),8]-diene-2-ol；cis-ρ-mentha-1(7),8-dien-2-ol；cis-p-mentha-1(7),8-dien-2-ol；cis-2-Methylen-5-isopropenyl-cyclohexanol；(+)-cis-p-Mentha-1(7),8-dien-2-ol；cis-1(7),8-p-Menthadien-2-ol；(1R,5R)-2-methylidene-5-prop-1-en-2-ylcyclohexan-1-ol
• CAS: 10374-04-6
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: PNVTXOFNJFHXOK-NXEZZACHSA-N

物化性质

• 沸点：
  71-72 °C(Press: 3 Torr)
• 密度：
  0.9457 g/cm3
• 保留指数：
  1204;1204;1206;1198;1205;1198

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  p-Menthadiene<1(7),8>-cis-ol-(2) 在 sodium dichromate 作用下， 生成 (+)-紫苏醛
  参考文献：
  名称：

  Naves,Y.-R.; Grampoloff,A.V., Bulletin de la Societe Chimique de France, 1960, p. 37 - 45

  摘要：

  DOI：
• 作为产物：
  描述：

  甜橙提取物 生成 p-Menthadiene-<1(7),8>-trans-ol-(2) 、 p-Menthadiene<1(7),8>-cis-ol-(2)
  参考文献：
  名称：

  Schenk,G.O. et al., Justus Liebigs Annalen der Chemie, 1964, vol. 674, p. 93 - 117

  摘要：

  DOI：

文献信息

• Studies towards the Taming of the ‘Carbocation’ in the Regioselective Ring Opening of Epoxides to Allylic Alcohols
  作者：William Motherwell、Helen Chapman、Karim Herbal

  DOI：10.1055/s-0029-1219373

  日期：2010.3

  Regioselective isomerisation of epoxides to allylic alcohols can be achieved using p-toluenesulfonic acid in the presence of 1,3-dimethylimidazolidin-2-one.

  在 1,3-二甲基咪唑啉-2-one 存在下，使用对甲苯磺酸可以实现环氧化物向烯丙醇的区域选择性异构化。
• Photosensitized Oxygenation of Olefins with Zinc Tetraphenylporphine-1,4-Diazabicyclo[2.2.2]octane Complex
  作者：Masako Sakuragi、Kunihiro Ichimura、Hirochika Sakuragi

  DOI：10.1246/bcsj.65.1944

  日期：1992.7

  more photoresistant sensitizer for singlet-oxygen oxygenation of olefins than in the absence of the amines. This is ascribed to the facts that ZnTPP forms a 1 : 1 complex with DABCO, and that DABCO coodinated to ZnTPP has no ability to quench singlet oxygen, as revealed by detection of singlet oxygen phosphorescence and product distributions in oxygenation of d-limonene, 1,2-dimethylcyclohexene, and 1-phenylcyclobutene

  在适量的胺如 1,4-二氮杂双环 [2.2.2] 辛烷 (DABCO) 和哌啶的存在下，四苯基卟啉锌 (ZnTPP) 不仅明显更有效，而且对单线态氧的光敏剂更有效烯烃的氧化比在没有胺的情况下进行。这归因于以下事实：ZnTPP 与 DABCO 形成 1:1 复合物，并且与 ZnTPP 配位的 DABCO 没有淬灭单线态氧的能力，正如检测单线态氧磷光和 d-柠檬烯氧化中的产物分布所揭示的那样，1 ,2-二甲基环己烯和1-苯基环丁烯。
• Active Oxygen Species and Structure Specificity of Antipsoriatic Anthrones
  作者：Klaus Müller

  DOI：10.1002/ardp.19883210703

  日期：——

  Twenty‐one analogues of the antipsoriatic compound dithranol were tested for their capability to produce 1O2 and O2.‐. A correlation was found between the production of active oxygen species and the minimum structure for the antipsoriatic activity of anthrone derivatives. The ability of the anthrones to sensitize the formation of 1O2 is a function of the deprotonated hydroxyl group at C‐1 associated

  测试了抗银屑病化合物地蒽酚的 21 种类似物产生 1O2 和 O2 的能力。发现活性氧物质的产生与蒽酮衍生物抗银屑病活性的最小结构之间存在相关性。蒽酮促进 1O2 形成的能力是 C-1 处去质子化羟基与蒽分子 C-9 处羰基相关联的函数；C-10 处的 CH2 - 部分引发自由基的形成，并负责产生 O2.-，而 O2.- 可通过取代 C-10 处的氢原子来防止。因为只有活性化合物地蒽酚、菊芋素、花椒大黄素-蒽酮和芦荟大黄素-蒽酮才能产生 1O2 和 O2。
• 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.