allohimachalol | 19435-77-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allohimachalol
• 英文别名: (4aR,5R,9aR)-1,1,4a,8-Tetramethyl-2,3,4,4a,5,6,7,9a-octahydro-1H-benzo[7]annulen-5-ol；(4aR,9R,9aR)-4,4,6,9a-tetramethyl-2,3,4a,7,8,9-hexahydro-1H-benzo[7]annulen-9-ol
• CAS: 19435-77-9
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: ZLJPQFLGGAYZAN-UMVBOHGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  allohimachalol 生成 (+)-himachalol
  参考文献：
  名称：

  The stereochemistry of allohimachalol

  摘要：

  DOI：

  10.1016/s0040-4039(01)85463-0

文献信息

• Synthesis, X-ray analysis, and antiviral evaluation of allohimachalol: Insights into stereoselectivity in epoxidation
  作者：Ilham Ait braim、Abdellatif Rafik、Ahmed Benharref、Ahmed Chekroun、Haydar Mohammad-Salim、Abdellah Zeroual、Asad Syed、Ali H. Bahkali、Shifa Wang、Ling Shing Wong、Jesus Vicente de Julian Ortiz

  DOI：10.1016/j.molstruc.2024.137660

  日期：2024.6

  experimental and theoretical studies on the epoxidation reaction of Allohimachalol with meta-chloroperbenzoic acid (m-CPBA). This reaction led to the formation of a new product, referred to as product 3, through a simultaneous rearrangement process. The compound structures were identified using spectroscopic techniques, including H and C NMR, along with X-ray diffraction. Furthermore, the electronic structures

  别洛马查洛是阿特拉斯雪松精油中的重要元素，通过蒸汽蒸馏获得，塑造了精油独特的香气。它的突出增强了雪松油独特的嗅觉特征，使其在香水和芳香疗法中具有价值。为了提高其反应活性，我们对别洛马查洛与间氯过苯甲酸（m-CPBA）的环氧化反应进行了实验和理论研究。该反应通过同时进行的重排过程形成了一种新产物，称为产物 3。使用光谱技术（包括 1H 和 13C NMR 以及 X 射线衍射）鉴定了化合物的结构。此外，通过使用密度泛函理论（DFT）在B3LYP/6-311G（d，p）水平上的理论计算研究了合成化合物的电子结构。对与不同反应途径相关的能量分布的分析产生了与实验观察结果一致的结果，证实了别洛马查洛环氧化反应与理论预测的一致性。此外，对 SARS-CoV-2 (6LU7) 和 HIV 的主要蛋白酶内的研究化合物进行了对接分析，表明化合物 3 有希望作为人类健康的潜在抗病毒药物。
• Autoxidation of allohimachalol
  作者：Koon-Sin Ngo、Geoffrey D. Brown

  DOI：10.1016/s0040-4020(99)00938-2

  日期：1999.12

  The tri-substituted (2,3)-double bond in allohimachalol (1) undergoes autoxidation in the presence of singlet molecular oxygen, resulting in tertiary and secondary allylic hydroperoxides 6 and 7. These autoxidation products may then participate in complex rearrangement reactions to yield seco-allohimachalanes, which have undergone carbon-carbon bond cleavage at the 2,3- or 3,4-positions. The observed autoxidation/reanangement reactions of 1 in vitro would account for the biogenesis of several allohimachalanes recently reported from the medicinal plant Illicium tsangii as natural products. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Allohimachalane, seco-allohimachalane and himachalane sesquiterpenes from Illicium tsangii
  作者：Koon-Sin Ngo、Geoffrey D. Brown

  DOI：10.1016/s0040-4020(98)01068-0

  日期：1999.1

  The dichloromethane extract of I. tsangii has yielded ten novel sesquiterpenes (1-4, 6-11) possessing or derived from the very rare allohimachalane skeleton in addition to one new himachalane (12) and a new megastigmane (14). It is suggested that the novel skeletons possesed by seco-allohimachalanes 8-11 are the result of carbon-carbon bond cleavage reactions associated with hydroperoxide autoxidation products (e.g. 6, 7) of the tri-substituted double bond. (C) 1998 Elsevier Science Ltd. All rights reserved.