(1S,4R,6R)-1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-6-ol | 66965-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1S,4R,6R)-1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-6-ol
• 英文别名: (1S,4R,6R)-1,3,3-trimethyl-2-oxa-bicyclo[2.2.2]octan-6-ol；(+)-2β-Hydroxycineole；2-endo-hydroxycineole；(1S)-6α-hydroxycineole；(1S,4R,6R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-ol
• CAS: 66965-45-5
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: YVCUGZBVCHODNB-MRTMQBJTSA-N

物化性质

• 沸点：
  238.7±8.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,4R,6R)-1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-6-ol 生成 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one
  参考文献：
  名称：

  PAYNE, G. B.;SOLOWAY, S. B.;POWELL, J. E.;ROMAN, S. A.;KOLLMEYER, W. D.

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-α-松油醇 在 sodium tetrahydroborate 、 monoperoxyphthalic acid 作用下， 以 乙醇 为溶剂， 生成 (1S,4R,6R)-1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-6-ol
  参考文献：
  名称：

  Carman, Raymond M.; Fletcher, Mary T., Australian Journal of Chemistry, 1984, vol. 37, # 5, p. 1117 - 1122

  摘要：

  DOI：

文献信息

• Preparation of biologically active substances and animal and microbial metabolites from menthols, cineoles and kauranes
  作者：Yoshinori Asakawa、Reiko Matsuda、Motoo Tori、Toshihiro Hashimoto

  DOI：10.1016/0031-9422(88)83033-4

  日期：1988.1

  and their structures elucidated by NMR spectroscopy. Some hydroxylated menthols showed plant growth inhibitory and strong mosquito repellent activity. Among the hydroxylated cineoles, microbial and animal metabolites of cineoles were included. From ent-kauranes, a plant growth inhibitory diterpene alcohol, (−)-16α-hydroxy kaurane was obtained along with 16α-kauran-13α-ol.

  摘要 间氯过苯甲酸或干臭氧氧化了六种单萜类化合物 l-薄荷醇、l-乙酸薄荷酯、异薄荷醇、新薄荷醇、1,4-桉树脑和 1,8-桉树脑和一种双萜烃 ent-kaurene。得到各种羟基化产物及其核磁共振谱阐明的结构。一些羟基化薄荷醇显示出植物生长抑制和强烈的驱蚊活性。在羟基化桉树脑中，包括桉树脑的微生物和动物代谢物。从 ent-kaurane 中获得了植物生长抑制性二萜醇 (-)-16α-羟基 kaurane 以及 16α-kauran-13α-ol。
• Cloning, Expression and Purification of Cindoxin, an Unusual Fmn-Containing Cytochrome P450 Redox Partner
  作者：David B. Hawkes、Kate E. Slessor、Paul V. Bernhardt、James J. De Voss

  DOI：10.1002/cbic.201000119

  日期：——

  Living in cin: Cindoxin is an FMN‐containing cytochrome P450 redox partner that mediates the transfer of electrons derived ultimately from NADPH to P450cin, which then catalyses the enantiospecific hydroxylation of cineole. The P450cin/cindoxin system is unique and represents a new cytochrome P450/redox partner class.

  生活在cin中：Cindoxin是一种含FMN的细胞色素P450氧化还原伙伴，它介导最终将NADPH衍生的电子转移至P450 cin，然后催化桉树脑的对映体特异性羟基化。P450 cin / cindoxin系统是独特的，代表了新的细胞色素P450 /氧化还原伴侣类别。
• Syntheses of Chiral 1,8-Cineole Metabolites and Determination of Their Enantiomeric Composition in Human Urine After Ingestion of 1,8-Cineole-Containing Capsules
  作者：Monika Schaffarczyk、Teodor Silviu Balaban、Michael Rychlik、Andrea Buettner

  DOI：10.1002/cplu.201200253

  日期：2013.1

  The chiral metabolites in human urine were investigated after ingestion of a 1,8‐cineole (eucalyptol)‐containing entero‐coated capsule (Soledum). For identification of the various enantiomers the enantiomerically pure (−/+)‐α2‐hydroxy‐1,8‐cineole, (−/+)‐β2‐hydroxy‐1,8‐cineole, (−/+)‐9‐hydroxy‐1,8‐cineole, and (−/+)‐2‐oxo‐1,8‐cineole were prepared. To achieve this aim, after acetylation of the synthesized

  摄入含1,8-桉树脑（桉树脑）的肠溶胶囊（Soledum）后，研究了人类尿液中的手性代谢物。为了鉴定各种对映异构体，对映体纯的（-/ +）-α2-羟基-1,8-桉树脑，（-/ +）-β2-羟基-1,8-桉树脑，（-/ +）-9-羟基制备了-1,8-桉树脑和（-/ +）-2-氧代-1,8-桉树脑。为实现这一目标，在合成的外消旋2-羟基和9-羟基-1,8-桉树脑被乙酰化后，猪肝酯酶或酵母介导的水解作用为（-）-醇及其对映异构体的对映体（+）-乙酸酯提供了对映体超过33–100％。通过拆分乙酸盐的水解获得的Dess-Martin高碘烷对醇（+）-α2-羟基-1,8-桉树脑的氧化，提供了相应的（+）-2-氧代-1,8-桉树脑，同时进行了氧化（-）-α2-羟基-1,8-桉树脑的化合物得到（-）-2-2-氧-1,8-桉树脑。使用这些标准品的七个代谢物（+/-）-α2-羟基-1,8-桉树脑，（+/-）-β2-羟基-1
• Oxidation of natural compounds catalyzed by Mn(III) porphyrin complexes
  作者：JoséA.S. Cavaleiro、Graça M.S.F.C. Nascimento、Maria G.P.M.S. Neves、Maria T. Pinto、Armando J.D. Silvestre、Maria G.H. Vicente

  DOI：10.1016/0040-4039(96)00145-1

  日期：1996.3

  The oxidation of 1,8-cineole (1) and methyl dehydroabietate (8b) by hydrogen peroxide, catalysed by Mn(III) porphyrin complexes, is reported. Five oxygenated products (2–6) have been obtained from reactions at positions 2 and 3 of 1,8-cineole and three oxygenated products (9–11) from the reaction at position 7 of methyl dehydroabietate.

  据报道，Mn（III）卟啉配合物催化过氧化氢氧化1,8-桉树脑（1）和脱氢松香酸甲酯（8b）。从1,8-桉树脑的2和3位反应获得了五个氧化产物（2–6），从脱氢松香酸甲酯的7位反应得到了三个氧化产物（9–11）。
• Enantiomeric Purity and Odor Characteristics of 2- and 3-Acetoxy-1,8-cineoles in the Rhizomes of <i>Alpinia </i><i>g</i><i>alanga</i> Willd.
  作者：Kikue Kubota、Yuki Someya、Reiko Yoshida、Akio Kobayashi、Tetsu-ichiro Morita、Hiroyuki Koshino

  DOI：10.1021/jf9807465

  日期：1999.2.1

  (S)-(+)-O-methylmandelate esters of trans- and cis-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5- and 6-ols (2- and 3-hydroxy-1,8-cineoles) were prepared, and eight diastereomers were separated. The absolute configuration of the asymmetric carbons of the cineole moiety of each diastereomer was determined by H-1 NMR data according to the Mosher theory. Each mandelate was reduced with LiAlHe4 to obtain optically pure hydroxy-1,8-cineoles, this being followed by acetylation to afford optically pure acetoxy-1,8-cineoles. These acetates were subjected to chiral GC, using a cyclodextrin column, and the enantiomeric purity of trans- and cis-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5- and 6-yl acetates in the aroma concentrate from the rhizomes of Alpinia galanga was determined as 93.9 (5S), 19.4 (5R), 63.5 (6R), and 100 (6R) % cc, respectively. The aroma character of each enantiomer was also evaluated by GC-sniffing.