2-ethyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene | 73371-45-6

• 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: 2-ethyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene
• 英文别名: 2-Ethylapopinene；2-Ethyl-bicyclo<3,1,1>-6,6-dimethylhept-2-en；2-Ethyl-6,6-dimethylbicyclo[3.1.1]hept-2-ene
• CAS: 73371-45-6
• 化学式: C₁₁H₁₈
• 分子量: 150.264
• InChiKey: ZWQAIGAZCBVYRW-UHFFFAOYSA-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-ethyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene 在 dioxane*SO₃ 作用下， 以 二氯甲烷 为溶剂， 生成 1-乙基-4-异丙基苯
  参考文献：
  名称：

  Sulfonation of terpene derivatives. Aluminum hydride desulfurization of sultones

  摘要：

  DOI：

  10.1021/jo00947a046
• 作为产物：
  描述：

  mesylate de nopol 在 lithium aluminium tetrahydride 作用下， 生成 2-ethyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene
  参考文献：
  名称：

  品系替代品

  摘要：

  衍生自pin烷的β-和Gg-不饱和过氧化物在二氯甲烷中的分解会导致瞬态叔pin基加合物自由基。反应的进行取决于不饱和的位置。在第一种情况下，分子内均溶取代产生功能性松香环氧化物。在第二种情况下，先进行β断裂再进行氢转移，会生成功能性的对薄荷酸过氧化物。

  DOI：

  10.1016/s0040-4020(01)85510-1

文献信息

• Hydroboration. 93. Convenient Conversion of Optically Pure 2-Organylapopinenes into the (2-Organylapoisopinyl)dihaloboranes Potentially Valuable for Asymmetric Synthesis via Chiral Organoboranes
  作者：Ulhas P. Dhokte、Herbert C. Brown

  DOI：10.1021/om960240g

  日期：1996.8.6

  Optically pure and sterically varied (2-organylapoisopinyl)dihaloboranes [RapBX2, R = Me (except for X = I), Et, Pr, i-Bu, Ph, i-Pr, X = Cl, Br, I], potentially important reagents for asymmetric synthesis, are conveniently prepared by the in situ reduction and hydroboration reaction of boron trihalide, trimethylsilane, and 2-organylapopinenes (2-R-apopinenes) under mild reaction conditions in essentially

  可能是光学纯且呈空间变化的（2-organylapoisopinyl）二卤环烷酮[RapBX 2，R = Me（X = I除外），Et，Pr，i -Bu，Ph，i -Pr，X = Cl，Br，I]，不对称合成的重要试剂可通过在温和的反应条件下原位还原三卤化硼硼，三甲基硅烷和2-有机基罂粟碱（2-R-罂粟碱）并进行硼氢化反应来制备，其定量产率基本可得。不幸的是，尽管更大体积的2-R-罂粟碱提供了所需的RapBI 2衍生物，但是不能通过该方法合成IpcBI 2（RapBI 2，R = Me）。
• Practical and General Alcohol Deoxygenation Protocol
  作者：Oliver P. Williams、Alyah F. Chmiel、Myriam Mikhael、Desiree M. Bates、Charles S. Yeung、Zachary K. Wickens

  DOI：10.1002/anie.202300178

  日期：——

  A new protocol for alcohol deoxygenation that functions across a wide range of alcohol structures is reported. This approach combines the reductive potency of carbon dioxide radical anion with acidic additives to promote the kinetically slow C(sp3)−O bond cleavage.

  据报道，一种新的醇脱氧方案可在多种醇结构中发挥作用。这种方法将二氧化碳自由基阴离子的还原能力与酸性添加剂相结合，以促进动力学上缓慢的 C(sp 3 )−O 键裂解。
• Brown, Herbert C.; Ramachandran, P. Veeraraghavan, Pure and Applied Chemistry, 1991, vol. 63, p. 307 - 316
  作者：Brown, Herbert C.、Ramachandran, P. Veeraraghavan

  DOI：——

  日期：——
• Hydroboration. 91. Improved Procedure for the Synthesis of Optically Pure Bis-adducts,N,N,N,'N'-Tetramethylethylenediamine.cntdot.2-organylapoisopinocampheylboranes, from the Corresponding 2-Organylapopinenes of Lower Optical Purity. Conversion of These Adducts into 2-Organylapoisopinocampheylboranes, Useful Asymmetric Hydroborating Reagents
  作者：Herbert C. Brown、Ulhas P. Dhokte

  DOI：10.1021/jo00088a016

  日期：1994.5

  The higher analogues of alpha-pinene, such as 2-ethyl-, 2-n-propyl-, 8-isobutyl-, 2-phenyl-, and 2-isopropylapopinenes, were treated with borane-methyl sulfide (BMS) in the stoichiometry of 1.2:1, respectively, in anhydrous tetrahydrofuran (THF) at 25 degrees C, obtaining an equilibrium mixture of 2-organylapoisopinocampheylboranes (2-R-apoisopinylborane, RapBH(2)) as major and bis(2-organylapoisopinocampheyl)borane [bis(2-R-apoisopinyl)borane, Rap(2)BH] as minor constituents. Treatment of the equilibrium mixture of boranes with tetramethylethylenediamine (TMEDA) at 34 degrees C readily and selectively provided the optically pure bis(2-organylapoisopinocampheylborane) T adducts, (RapBH(2))(2).TMEDA, in satisfactory yield. This reaction is quite general and appears to be broadly applicable to the conversion of the sterically bulkier 2-organylapopinenes (2-R-apopinenes) with widely varied steric requirements and lower optical purity (87-92% ee) into the corresponding optically pure (RapBH(2))(2).TMEDA derivatives, approaching greater than or equal to 99% ee. Treatment of the crystalline bis-adduct in ethyl ether with BF3.EE precipitates (BF3)(2).TMEDA and provides RapBH(2) of essentially greater than or equal to 99% ee, enantiomerically purer than the 2-R-apopinenes of 87-92% ee utilized for these preparations.
• BRAVN, H. C.;JADHAV, P. K., J. ORG. CHEM., 1984, 49, N 21, 4089-4091
  作者：BRAVN, H. C.、JADHAV, P. K.

  DOI：——

  日期：——