(+)-2-ethylapopinene | 117019-46-2

• 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-ethylapopinene
• 英文别名: (1S,5R)-2-ethyl-6,6-dimethylbicyclo[3.1.1]hept-2-ene
• CAS: 117019-46-2
• 化学式: C₁₁H₁₈
• 分子量: 150.264
• InChiKey: ZWQAIGAZCBVYRW-NXEZZACHSA-N

物化性质

• 沸点：
  181.0±7.0 °C(Predicted)
• 密度：
  0.871±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (+)-2-ethylapopinene 在 natronlauge 、 Peressigsaeure 、 sodium carbonate 、 对甲苯磺酸 、 zinc dibromide 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 7.25h， 生成 4-(3-Ethyl-2,2-dimethylcyclopent-3-en-1-yl)-2-methylbut-2-enal
  参考文献：
  名称：

  Synthese eines ?Ethyl-Brahmanols?

  摘要：

  The synthesis of the title compound (11) from ethylapopinene (5) by oxydation to the epoxide (6), rearrangement to ''ethyl-alpha-campholene aldehyde'' (7) and its aldol condensation is described.

  DOI：

  10.1002/prac.19933350509
• 作为产物：
  描述：

  桃金娘烯醇 在 乙醚 、 三溴化磷 作用下， 生成 (+)-2-ethylapopinene
  参考文献：
  名称：

  Rupe, Justus Liebigs Annalen der Chemie, 1927, vol. 459, p. 179

  摘要：

  DOI：

文献信息

• Asymmetric Synthesis using Organoboranes. Relative Effectiveness of the B-Halobis(terpenyl)boranes for the Enantioselective Halogenative Cleavage of Representative meso-Epoxides
  作者：Chandra D. Roy、Herbert C. Brown

  DOI：10.1071/ch07118

  日期：——

  A comparative study of the relative effectiveness of various Ter2BX, such as dEap2BX, lEap2BX, 2-dIcr2BX, 4-dIcr2BX, and lCleap2BX along with dIpc2BX for the asymmetric ring opening of three representative meso-epoxides (cyclohexene, cyclopentene, and cis-2,3-butene oxides) is reported. Among all the reagents studied, 2-dIcr2BCl (78–80%) demonstrated significant improvement in enantiomeric excess over

  比较研究各种 Ter2BX，如 dEap2BX、lEap2BX、2-dIcr2BX、4-dIcr2BX 和 lCleap2BX 以及 dIpc2BX 对三种代表性中间环氧化物（环己烯、环戊烯和 cis-2）的不对称开环的相对有效性,3-丁烯氧化物）被报道。在所研究的所有试剂中，2-dIcr2BCl (78–80%) 与先前探索的试剂 dIpc2BCl (41%) 相比，对映体过量有显着改善，特别是对于内消旋环己烯氧化物。尽管所有这三种试剂 dIpc2BBr、dEap2BBr 和 2-dIcr2BBr 都从内消旋环己烯氧化物中提供了相当的对映体富集的 2-溴环己烷-1-醇 (76-86%)，但基于芳烃的试剂 2-dIcr2BBr 在内消旋环戊烯氧化物 (67%) 和内消旋顺式 2 的对映体过量，3-氧化丁烯 (78%) 比使用先前报道的试剂 dIpc2BBr (分别为 57% 和 61%)
• Substitution reaction with participation of organoaluminum compounds. Communication 5. Skeletal rearrangements in reactions of trialkylalanes with tosylates of certain homoallylic alcohols of the terpene series
  作者：G. A. Tolstikov、A. Yu. Spivak、L. M. Khalilov、E. V. Vasil'eva、S. I. Lomakina、I. A. Ivanova

  DOI：10.1007/bf00948514

  日期：1985.8
• Hydroboration of Terpenes. 11. Convenient Method for Upgrading 2-Organylapopinenes to High Optical Purity by Reaction of 2-Organylapoisopinocampheylboranes with Suitable Dienes Followed by Displacement with Acetaldehyde
  作者：Herbert C. Brown、Ulhas P. Dhokte

  DOI：10.1021/jo00097a065

  日期：1994.9
• Hydroboration. 94. Rates of Hydroboration of 2-Organylapopinenes with 9-Borabicyclo[3.3.1]nonane, Providing <i>B</i>-(2-Organylapoisopinocampheyl)-9-borabicyclo[3.3.1]nonanes, Potentially Valuable for the Asymmetric Reduction of Prochiral Ketones
  作者：Ulhas P. Dhokte、Herbert C. Brown

  DOI：10.1021/jo9617169

  日期：1997.2.1

  Five representative enantiomerically pure, hindered terpenes, derived from a-pinene, namely 8-organylapopinenes (2-R-apopinenes, R = Et, Pr, i-Bu, Ph, and i-Pr) have been treated with 9-borabicyclo[3.3.1]nonane (9-BBN) in a 1:1 molar ratio in THF at 24 degrees C and the rate of hydroboration followed. Increasing the bulk of the 2-R group from the 2-methyl of alpha-pinene (Ipc, 2-methylapopinene) to 8-ethyl-(Eap), to 2-propyl-(Prap), to 2-isobutyl-(i-Bap), to 2-phenyl-(Pap), and to 2-isopropyl-(i-Prap) significantly lowers the rate of hydroboration with 9-BBN. Thus, the rate of hydroboration of alpha-pinene with 9-BBN is faster than the rates for the 2-R-apopinenes studied. The sterically bulkier 2-isobutyl-, 2-phenyl-, and 2-isopropylapopinenes reveal a significantly slower rate of hydroboration with 9-BBN. At an elevated temperature, 65 degrees C, the reaction of 9-BBN (1.0 equiv) with a slight excess of optically pure 2-isobutyl- and 2-phenylapopinenes (1.10-1.20 equiv), under neat conditions, is facilitated to provide the desired B-(2-organylapoisopinocampheyl)-9-borabicyclo[3.3.1]nonanes (2-organyl = isobutyl- and phenyl) in quantitative yield. Unfortunately, this synthesis failed for 2-isopropylapopinene. Fortunately, an indirect synthesis proved satisfactory. Treatment of enantiomerically pure (2-isopropylapoisopinocampheyl)borane, i-PrapBH(2), conveniently synthesized from 2-isopropylapopinene, and 1,5-cyclooctadiene (1,5-COD), provided, after thermal isomerization, the desired 1:1 adduct [B-(2-Rap)-9-BBN; 2-Rap = 2-isopropylapoisopinyl skeleton] in quantitative yield. Consequently, five of the 2-R-apopinenes, R = Et, Pr, i-Bu, Ph, and i-Pr, have been successfully converted into the corresponding B-(2-Rap)-9-BBN derivatives.
• BROWN, HERBERT C.;VEERARAGHAVAN, RAMACHANDRAN P.;WEISSMAN, STEVEN A.;SWAM+, J. ORG. CHEM., 55,(1990) N6, C. 6328-6333
  作者：BROWN, HERBERT C.、VEERARAGHAVAN, RAMACHANDRAN P.、WEISSMAN, STEVEN A.、SWAM+

  DOI：——

  日期：——