2,3-epoxy-pinan-10-ol | 104320-46-9

• 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: 2,3-epoxy-pinan-10-ol
• 英文别名: Myrtenol epoxide；(7,7-dimethyl-3-oxatricyclo[4.1.1.02,4]octan-2-yl)methanol
• CAS: 104320-46-9
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: OLFKBUNTMDJAFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  245.6±8.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-epoxy-pinan-10-ol 在 potassium tert-butylate 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 (E)-6,6-dimethyl-2-<(methoxymethoxy)methylene>bicyclo<3.1.1>heptan-3-ol
  参考文献：
  名称：

  Heteroatom-Assisted Isomerization of Oxiranes to Allylic Alcohols Promoted by Bases

  摘要：

  The isomerization of alkoxy-substituted oxiranes to hydroxy-substituted ene ethers promoted by mixed metal bases has been investigated. The structure of the oxirane substrate (the number, the position, and the type of alkyl substituents on the ring) plays an important role in driving the stereoselectivity of the reaction. Disubstituted oxiranes show a predictable preference for the E-ene ether while trisubstituted substrates give either a mixture of stereoisomers or the E-ene ether exclusively, depending on the location of the third alkyl substituent.

  DOI：

  10.1021/jo00096a020
• 作为产物：
  描述：

  桃金娘烯醇 在 氧气 、 异丁醛 作用下， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以63%的产率得到2,3-epoxy-pinan-10-ol
  参考文献：
  名称：

  以有机碳酸酯为绿色溶剂的生物可再生烯烃催化好氧环氧化

  摘要：

  环氧化物是工业和有机合成中的重要产品。然而，对于大规模应用，由于在非安全条件下使用有毒反应物/溶剂，这些方法已经过时。在这项工作中，我们提出了一种更安全的烯烃环氧化工艺，该工艺符合绿色化学原理。使用环境友好型分子氧作为最终氧化剂、异丁醛作为牺牲试剂和基于非贵金属（钴）的坚固固体材料作为非均相催化剂，在温和条件下对一系列生物可再生基材进行了选择性环氧化。几种有机碳酸酯被认为是现代级别的可持续溶剂，并且在环氧化中很少被开发，已被研究作为该反应的反应介质。

  DOI：

  10.1016/j.mcat.2022.112400

文献信息

• Epoxidations with 30% hydrogen peroxide catalyzed by tungstic acid in buffered media
  作者：Denis Prat、Robert Lett

  DOI：10.1016/s0040-4039(00)84079-4

  日期：1986.1

  The scope of the tungstic acid catalyzed hydrogen peroxide epoxidation of olefinic alcohols is examined, at room temperature, in buffered protic media. Epoxidation occurs with complete retention of configuration for both cis and trans alkenes. Chemoselectivity is discussed with respect to the olefinic alcohol structure and olefin substituents.

  在室温下，在质子缓冲介质中，考察了钨酸催化烯烃醇的过氧化氢环氧化的范围。环氧化发生时，顺式和反式烯烃都完全保留构型。关于烯烃醇结构和烯烃取代基，讨论了化学选择性。
• Metal-Catalyzed Oxidations with Pinane Hydroperoxide:  A Mechanistic Probe To Distinguish between Oxometal and Peroxometal Pathways
  作者：H. E. B. Lempers、A. Ripollès i Garcia、R. A. Sheldon

  DOI：10.1021/jo971270b

  日期：1998.3.1

  The relative reactivities of tert-butyl hydroperoxide (TBHP) and pinane hydroperoxide (PHP) in metal (Cr, Mo, Ru, Se, V, and Zr)-catalyzed oxidations were compared. When these oxidations involve rate-limiting oxygen transfer from a peroxometal species to the substrate huge differences between TBHP and PHP were observed, e.g., molybdenum-catalyzed epoxidation of cyclohexene with TBHP gave a 98% yield while PHP gave 0%. When the reaction involves reaction of an oxometal species with the substrate as the rate-limiting step, little or no difference is observed, e.g., the selenium-catalyzed allylic oxidation of beta-pinene gave a 96% and 99% yield with TBHP and PHP, respectively. Small but significant differences are observed when reoxidation of the catalyst by the hydroperoxide to the active oxometal species is the rate-limiting step; e.g., the chromium-catalyzed oxidation of carveol gave carvone in 89% and 24% yield with TBHP and PHP, respectively. Hence, the effect of RO2H structure on rate is dependent on the rate-limiting step.
• Microencapsulated VO(acac)₂:  Preparation and Use in Allylic Alcohol Epoxidation
  作者：Alessandra Lattanzi、Nicholas E. Leadbeater

  DOI：10.1021/ol0257474

  日期：2002.5.1

  Microencapsulated VO(acac)(2) [MC-VO(acac)(2)] has been prepared and screened with success as a catalyst for the epoxidation of allylic alcohols using tert-butyl hydroperoxide as oxidant. The reactions are run in hexane at room temperature. The MC-VO(acac)(2) is reusable without significant loss of activity.
• Arbusow; Frinowskaja, Doklady Akademii Nauk SSSR, 1957, vol. 112, p. 427
  作者：Arbusow、Frinowskaja

  DOI：——

  日期：——
• PRAT, D.;DELPECH, B.;LETT, R., TETRAHEDRON LETT., 1986, 27, N 6, 711-714
  作者：PRAT, D.、DELPECH, B.、LETT, R.

  DOI：——

  日期：——