(1R,5R)-2(10),3-pinadiene | 23733-90-6

• 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,5R)-2(10),3-pinadiene
• 英文别名: verbenene；(1R)-pina-2(10),3-diene；(1R)-Pina-2(10),3-dien；(+)-Verbenen；Verbenen；(1R,5R)-6,6-dimethyl-4-methylidenebicyclo[3.1.1]hept-2-ene
• CAS: 23733-90-6
• 化学式: C₁₀H₁₄
• 分子量: 134.221
• InChiKey: YOQFOABVDRBYCG-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (1R,5R)-2(10),3-pinadiene 生成 1-<2-Methyl-propen-(1)-yl>-cyclohexadien-(1,5)
  参考文献：
  名称：

  Die Pyrolyse von（+）-韦尔本

  摘要：

  已发现马鞭草的热解可产生39％的异丁烯基环己-1,3-二烯（3），29％的o -mentha-1（7），5,8-三烯（2）和两个双键-环己二烯（3）的-异构体（4和5）。通过催化还原成饱和烃证明了结构，并由2,3-二氢苯甲醛合成了异丁烯基环己-1,3-二烯。

  DOI：

  10.1002/hlca.19690520510
• 作为产物：
  描述：

  beta-pinene 在 lead(IV) acetate 、 palladium diacetate 、 三苯基膦 作用下， 生成 (1R,5R)-2(10),3-pinadiene
  参考文献：
  名称：

  衍生自 (1R,5R)-2(10),3-Pinadiene 的顺式氧化钯配合物及其在 Pd(II) 催化的 2-(trans-2-Butenyl) 苯酚的对映选择性环化中的应用

  摘要：

  (1R,5R)-2(10),3-Pinadiene，当用 MeOH 中的 Na2PdCl4 或 AcOH 和 NaCl 中的 Pd(OAc)2 处理时，得到二-μ-氯-双 [(3,2,10-η -顺-4-甲氧基或乙酰氧基蒎烯）钯（II）]（4a）或（4b），分别...

  DOI：

  10.1246/bcsj.58.3282

文献信息

• ——
  作者：N. I. Kuznetsova、L. I. Kuznetsova、N. V. Kirillova、L. M. Pokrovskii、L. G. Detusheva、J.-E. Ancel、V. A. Likholobov

  DOI：10.1023/a:1025688908667

  日期：——

  Oxidation of cyclohexene and alpha-pinene with an O-2-H-2 mixture in the catalytic systems containing Pt or Pd and heteropoly compounds (HPC) was studied. The main oxidation products are epoxides, allyl alcohols, and ketones. The highest yield of the oxidation products was obtained in the presence of the platinum catalyst in combination with HPC PWII or PWIIFe. The reaction mechanism was proposed. A relationship between the HPC composition and the nature of intermediates involved in oxidation was examined.
• Coxon,J.M. et al., Australian Journal of Chemistry, 1971, vol. 24, p. 1481 - 1486
  作者：Coxon,J.M. et al.

  DOI：——

  日期：——
• Autoxidation of α-Pinene²
  作者：R. N. Moore、C. Golumbic、G. S. Fisher

  DOI：10.1021/ja01587a022

  日期：1956.3
• Evidence for 2-hexene-1,6-diyl diradicals accompanying the concerted Diels-Alder cycloaddition of acrylonitrile with nonpolar 1,3-dienes
  作者：Yufei Li、Anne Buyle Padias、H. K. Hall

  DOI：10.1021/jo00077a025

  日期：1993.12

  The spontaneous reactions of a series of alkyl 1,3-dienes with acrylonitrile (AN) were investigated. Reproducible spontaneous copolymerizations were shown to compete with the expected concerted [4 + 2] cycloadditions. For dienes which exist in s-cis/s-trans equilibrium, both copolymer and cycloadduct are formed. Kinetic measurements show that the alternating copolymerization and cycloaddition are two independent parallel second order reactions. With 1,3-cyclohexadiene and 1,2-dimethylenecyclohexane, for which s-gauche is in equilibrium with s-cis, copolymerization still competes with cycloaddition. The s-trans-locked verbenene forms only copolymer, while s-cis-locked cyclopentadiene and 1,2-dimethylenecyclopentane form only cycloadduct rapidly. Our explanation involves a 2-hexene- 1,6-diradical, formed by combination between the terminal carbons of the s-gauche or s-trans diene and acrylonitrile. This does not cyclize but initiates copolymerization. Competitively s-cis conformer undergoes classical concerted [4 + 2] addition.
• The Synthesis of cis- and trans-δ-Pinenes via Hydroboration of Verbenene
  作者：G. Zweifel、C. C. Whitney

  DOI：10.1021/jo01350a071

  日期：1966.12