(+)-(1R,5R)-apopinene | 43161-64-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: (+)-(1R,5R)-apopinene
• 英文别名: (+)-alpha-pinene；α-pinene；apopinene；(+)-(1R,5R)-2-apopin-3-ene；Apopinen；(1R,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene
• CAS: 43161-64-4
• 化学式: C₉H₁₄
• 分子量: 122.21
• InChiKey: SUEFRHDDZDWKFN-JGVFFNPUSA-N

物化性质

• 沸点：
  137.4±7.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 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)-apopinene 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 dilithium tetrachlorocuprate 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 3.0h， 生成 trans-4-Ethyl-6.6-dimethyl-bicyclo<3.1.1>hept-2-en
  参考文献：
  名称：

  Apopinene 4-烷基化衍生物的制备

  摘要：

  格氏试剂与溴-Apopinene偶联，后者是通过NBS处理Apopinene制备的，可高产率生成Apopinene的4-烷基化衍生物。特别令人感兴趣的是反式δ-pine烯的方便制备。这些新化合物的立体化学是基于NMR的考虑而建立的。

  DOI：

  10.1016/s0040-4020(01)99387-1
• 作为产物：
  描述：

  (-)-α-蒎烯 生成 (+)-(1R,5R)-apopinene
  参考文献：
  名称：

  Yates,P.; Hambly,G.F., Canadian Journal of Chemistry, 1979, vol. 57, p. 1668 - 1678

  摘要：

  DOI：

文献信息

• New chiral organosulfur donors related to bis(ethylenedithio)tetrathiafulvalene
  作者：Songjie Yang、Andrew C. Brooks、Lee Martin、Peter Day、Melanie Pilkington、William Clegg、Ross W. Harrington、Luca Russo、John D. Wallis

  DOI：10.1016/j.tet.2010.06.034

  日期：2010.8

  with structures related to BEDT-TTF, have been synthesised for use in the preparation of organic metals, starting either by double nucleophilic substitutions on the bis-mesylate of 2R,4R-pentane-2,4-diol or by a cycloaddition with subsequent elimination of acetic acid on the enol acetate of (+)-nopinone. Crystal structures of some of their radical cation triiodides salts and TCNQ complexes are reported

  已经合成了六种具有与BEDT-TTF相关结构的新的对映纯手性有机硫供体，用于制备有机金属，方法是从2 R，4 R-戊烷-2,4的双甲磺酸酯上进行双亲核取代。-二醇或通过环加成反应，然后在（+）-去甲酮的烯醇乙酸酯上消除乙酸。据报道其某些自由基阳离子三碘化物盐和TCNQ配合物的晶体结构。
• Regio- and stereoselective synthesis of constrained enantiomeric β-amino acid derivatives
  作者：Zsolt Szakonyi、Tamás A. Martinek、Reijo Sillanpää、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2008.09.026

  日期：2008.10

  Chlorosulfonyl isocyanate addition to (−)- and (+)-apopinene furnished monoterpene-fused β-lactams in highly regio- and stereospecific reactions. β-Lactams 5 and 13 exhibited reactivities similar to those of the cycloalkane-fused analogs and were easily converted to the β-amino acid and its protected derivatives. The base-catalyzed isomerization of the cis-amino ester afforded the corresponding trans-amino

  （-）-和（+）-Apopinene的氯磺酰基异氰酸酯可在高度区域和立体特异性反应中提供单萜融合的β-内酰胺。β-内酰胺5和13的反应性类似于环烷烃融合类似物，并易于转化为β-氨基酸及其受保护的衍生物。顺式-氨基酯的碱催化异构化以优异的产率提供了相应的反式-氨基酸对映体。完全的异构化是由稳定性差异解释的，该稳定性差异是由顺式和反式非对映异构体之间的从头算计算得出的。
• [EN] 1,3-HETEROCYCLES CONDENSED WITH MONOTERPENE SKELETON, THEIR USE AND PHARMACEUTICAL COMPOSITIONS COMPRISING SUCH COMPOUNDS<br/>[FR] HÉTÉROCYCLES-1,3 CONDENSÉS AVEC UN SQUELETTE MONOTERPÉNIQUE, UTILISATION DE CEUX-CI ET COMPOSITIONS PHARMACEUTIQUES COMPRENANT DE TELS COMPOSÉS
  申请人：BIOBLOCKS MAGYARORSZAG GYOGYSZ

  公开号：WO2010070365A1

  公开（公告）日：2010-06-24

  The invention relates to chiral compounds with monoterpene skeleton of general formula (I) - where in the formula X stands for O or H2; W stands for O, S, N-R2 or Ph-R3; Y stands for O or N-R4; R1 stands for H, C1-4Alk or (C2)1-4-Ph; R2 stands for C1-4Alk or Ph-R3; R3 stands for H, C1-4Alk, C1-4Alk-O or Hlg; R4 stands for H or Ph; and one of the signs --- means the presence of a double bond and the other means the absense of a double bond, with the proviso that only one of W and Y may simultaneously stand for oxygen - as well as to their prodrugs and salts formed with pharmaceutically acceptable acids. Furthermore, the invention relates to cytostatic pharmaceutical compositions comprising one or more compounds of general formula (I) and usual inert pharmaceutical carriers and/or auxiliary agents, to the use of the compounds of general formula (I) for preparing cytostatic pharmaceutical compositions as well as to the treatment and/or curing of cancerous illnesses.

  本发明涉及具有单萜骨架的手性化合物，其通式为（I）-其中在式中，X代表O或H2; W代表O、S、N-R2或Ph-R3; Y代表O或N-R4; R1代表H、C1-4Alk或（C2）1-4-Ph; R2代表C1-4Alk或Ph-R3; R3代表H、C1-4Alk、C1-4Alk-O或Hlg; R4代表H或Ph; 而---符号之一表示存在双键，另一个表示不存在双键，但W和Y中只有一个可以同时代表氧-以及它们的前药和与药学上可接受的酸形成的盐。此外，本发明还涉及包含一种或多种通式（I）化合物和通常的惰性药物载体和/或辅助剂的细胞毒药物组合物，以及使用通式（I）化合物制备细胞毒药物组合物以及治疗和/或治愈癌症疾病的方法。
• Isoxazole derivatives of alpha-pinene isomers: Synthesis, crystal structure, spectroscopic characterization (FT-IR/NMR/GC–MS) and DFT studies
  作者：Serpil Eryılmaz、Melek Gül、Ersin İnkaya、Murat Taş

  DOI：10.1016/j.molstruc.2015.11.079

  日期：2016.3

  ground state and geometric parameters were compared with the X-ray analysis results of the structure. Results of the experimental FT-IR and NMR spectral analysis were examined in order to determine the compliance with vibrational frequencies, 1H NMR and 13C NMR chemical shifts values by using the Gauge-Independent Atomic Orbital (GIAO) method calculated over the optimized structure. Besides molecular

  摘要 本文通过1,3-偶极环加成反应合成了α-蒎烯异恶唑衍生物（3a-bc, 4a-b），并用FT-IR、1H NMR、13C NMR和GC-MS进行了表征。异恶唑 (C21H23NO) 化合物 (4a) 6,6,7a,-trimethyl-3-(naphthalen-2-yl)-3a,4,5,6,7,7a-hexahydro-5,7-methanobenzo[d] 是用 X 射线单晶衍射技术表征。该化合物在单斜空间群 P 212121 中结晶，Z = 4。通过应用密度泛函理论 (DFT/B3LYP) 方法使用 6-31G(d,p) 和 6-311 + G 优化化合物的分子几何结构(d,p) 基态和几何参数的基组与结构的 X 射线分析结果进行了比较。检查实验 FT-IR 和 NMR 光谱分析的结果以确定与振动频率的一致性，1H NMR 和 13C NMR 化学位移值通过使用与规范无关的原子轨道
• Catalytic epoxidation of cyclic alkenes with air over CoOx/zeolite heterogeneous catalysts
  作者：X.-T. Ma、X.-H. Lu、C.-C. Wei、Z.-S. Zhao、H.-J. Zhan、D. Zhou、Q.-H. Xia

  DOI：10.1016/j.catcom.2015.04.017

  日期：2015.7

  The supported CoOx/zeolites have been prepared and applied for the epoxidation of cyclic alkenes with air. The catalysts are characterized by powder X-ray diffraction (XRD), ultraviolet-visible spectroscopy (UV-vis) and scanning electron microscope (SEM). Among these CoOx/zeolite catalysts, 2.4% CoOx/Y exhibits the best catalytic activity for the epoxidation of cis-cyclooctene with 612 mol% conversion and 98.8 mol% selectivity of epoxide. Some factors such as the kind of zeolites, the oxidants, the solvents, the Co contents, the reaction temperature and time play important roles in controlling the epoxidation. The recyclable stability of the 2.4% CoOx/Y catalyst is confirmed. (C) 2015 Elsevier B.V. All rights reserved.