Apopinene was synthesized from myrtenal by catalytic decarbonylation followed by either hydrogenation to generate dihydroapopinene or Simmons-Smith cyclopropanation to generate exo-(1R,2R)-7,7-dimethyltricyclo[4.1.1.0^2,4]octane (cyclopropanated apopinene, CPA). Key fuel properties of apopinene and the two derivative fuels were evaluated including density, heat of combustion, and low temperature viscosity. CPA exhibited a density of 0.918 g mL⁻¹ and a volumetric net heat of combustion (NHOC) 20 % higher than the lower limit for conventional jet fuel. This exceptional NHOC is a result of the high density of the tricyclic compound and the ring strain of the bridging cyclobutane and fused cyclopropane groups. Dihydroapopinene exhibited a high freezing point that will limit its applications as a jet fuel blendstock. In contrast, no freezing point down to −80 °C was observed for CPA via differential scanning calorimetry (DSC). In addition, CPA exhibited a moderate kinematic viscosity of 10.11 mm² s⁻¹ at −20 °C and 22.76 mm² s⁻¹ at −40 °C. This work demonstrates that fuels with both high energy densities and excellent low temperature properties can be generated from bio-based substrates through cyclopropanation reactions.

Apopinene 由桃金娘醛通过催化脱羰基合成，然后氢化生成二氢 apopinene 或 Simmons-Smith 环丙烷化生成外型-(1R,2R)-7,7-二甲基三环[4.1.1.0 2,4]^辛烷（环丙烷化 apopinene，CPA）。评估了 apopinene 和两种衍生燃料的关键燃料特性，包括密度、燃烧热和低温粘度。CPA的密度为0.918 g mL ^-1体积净燃烧热 (NHOC) 比传统喷气燃料的下限高 20%。这种特殊的 NHOC 是三环化合物的高密度以及桥接环丁烷和稠合环丙烷基团的环张力的结果。二氢阿蒎烯表现出高凝固点，这将限制其作为喷气燃料混合物的应用。相比之下，通过差示扫描量热法 (DSC) 观察到 CPA 的凝固点没有降至 -80 °C。此外，CPA在-20°C和22.76 mm ² s ^{-1下表现出中等的运动粘度，分别为10.11 mm 2 s -1 和22.76 mm 2} s ^-1在-40°C。这项工作表明，可以通过环丙烷化反应从生物基基质中生成具有高能量密度和优异的低温性能的燃料。