dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on | 6616-69-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on
• 英文别名: (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-7,8,10,10a-tetrahydro-6H-benzo[c]chromen-9(6aH)-one；(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-9-one
• CAS: 6616-69-9；16964-48-0；16964-51-5；52195-11-6；60761-09-3；63790-37-4；138383-58-1
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: YHIZWEDKQCYPIV-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 苄基三乙基氯化铵 、 lithium carbonate 、 lithium bromide 、 magnesium bromide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 6a,7,8,10a-四氢-1-羟基-6,6-二甲基-3-戊基-6H-二苯并(b,d)吡喃-9-甲醇
  参考文献：
  名称：

  The synthesis of some 11-substituted tetrahydrocannabinol metabolites

  摘要：

  9-溴-11-酮-大麻酚（5）是通过经过环氧磺酮4处理的酮大麻酚3b制备的。 溴醛5的脱溴反应可以控制，从而得到热力学上更稳定的Δ8-醛2c，或者通过分子内辅助消除得到Δ9-醛1c。 对不饱和醛的还原分别产生了烯丙醇代谢物2a和1a。

  DOI：

  10.1139/v82-403
• 作为产物：
  描述：

  3,5-二羟基戊苯 在 三氯化铝 、 水 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on
  参考文献：
  名称：

  The synthesis of some 11-substituted tetrahydrocannabinol metabolites

  摘要：

  9-溴-11-酮-大麻酚（5）是通过经过环氧磺酮4处理的酮大麻酚3b制备的。 溴醛5的脱溴反应可以控制，从而得到热力学上更稳定的Δ8-醛2c，或者通过分子内辅助消除得到Δ9-醛1c。 对不饱和醛的还原分别产生了烯丙醇代谢物2a和1a。

  DOI：

  10.1139/v82-403

文献信息

• Synthesis and pharmacological activity of some 9-substituted .DELTA.8-tetrahydrocannabinol (THC) analogs
  作者：Lauri R. Robertson、Richard P. Duffley、Raj K. Razdan、Billy R. Martin、Louis S. Harris、William L. Dewey

  DOI：10.1021/jm00370a023

  日期：1984.4

  8-tetrahydrocannabinol acetate (3) by the reaction of ethyl and methyl Grignard reagents, respectively. Biological activity indicated that a methyl group at the C-9 position is, thus far, optimum for producing hypoactivity and hypothermia in mice. In addition, hydroxyethyl substitution at position 9 reduced and antinociceptive activity of delta 8-THC, in contrast to the increased activity reported for hydroxymethyl

  合成了几种9-取代的δ8-四氢大麻酚（δ8-THC）类似物，并评估了其在小鼠中的生物学活性。通过分别向（-）-9-nor-9-氧代六氢大麻酚（1）中添加苯基锂和正丁基锂，​​然后脱水而制得具有苯基（2b）和丁基（2c）取代基的化合物，然后进行脱水， 2d），PhCH2（2e）和Ph（CH2）2（2f）衍生物是通过格氏反应并随后脱水合成的。由（-）-9-去甲-9-甲酰基-δ8-四氢大麻酚乙酸酯（3）通过乙基的反应制备在C-9处具有C2H5CH（OH）（2g）和CH3CH（OH）（2h）取代基的化合物和甲基格氏试剂。生物学活性表明，到目前为止，C-9位置的甲基最适合在小鼠中产生机能减退和体温过低。此外，
• Synthesis of 5′-(2H3)-(−)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol methyl ester methyl ether
  作者：Marcus A. Tius、G.S.Kamali Kannangara

  DOI：10.1016/s0040-4020(01)85608-8

  日期：1992.1

  A synthesis of 5′-(2H3)-(−)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol methyl ester methyl ether (4) has been accomplished from α-bromoenone 10. The key steps are the stereocontrolled cyclobutane ring opening of the cuprate adduct 18 and the cyclization of the cyclohexenyl triflate 21 with excess iodotrimethylsilane to produce Δ9-cyclohexenyl triflate 22. An efficient, stereospecific synthesis of optically

  的5'的合成- （2 ħ 3） - （ - ） - 11-NOR -9-羧基- Δ 9 -四氢大麻酚甲酯甲基醚（4）已被从α-bromoenone完成10。的关键步骤是铜酸盐加成物的立体控制环丁烷环开口18和环己烯基三氟甲磺酸酯的环化21用过量的三甲基碘硅烷，以产生Δ 9环己烯基三氟甲磺酸酯22。还已经完成了光学活性的（-）-d11-nor-9-酮-六氢大麻酚（8）的高效立体定向合成。
• TEST KIT FOR THE QUANTITATIVE DETERMINATION OF NARCOTIC DRUGS
  申请人：CHIRON AS

  公开号：US20150204893A1

  公开（公告）日：2015-07-23

  A test kit for the quantitative determination of narcotic drugs comprising (A) series of sealed vessels, each vessel containing a deuterium free isotopologue of a narcotic drug in exactly defined concentrations and quantities, wherein the isotopologue differs from vessel to vessel and—wherein the quantities of the isotopologue differ from vessel to vessel or are the same for all vessels; and/or (B) series of sealed vessels, each vessel containing in exactly defined concentrations and quantities the same isotopologue in quantities which differ from vessel to vessel; wherein the free isotopologues are selected from narcotic drugs; prodrugs, salts, solvates, hydrates and polymorphs and contain at least three stable isotopes selected from the group consisting of 13 C, 15 N and 18 O in the molecule with a degree of labeling of at least 95 mol-%; the use of the test kit and a method for quantitatively determining narcotic drugs.

  一种用于定量测定麻醉药物的检测试剂盒，包括（A）一系列密封容器，每个容器中含有一种去氘同位素麻醉药物，其浓度和数量均被精确定义，其中同位素从容器到容器不同，同位素的数量在容器到容器之间不同或对所有容器都相同；和/或（B）一系列密封容器，每个容器中含有相同的同位素，其浓度和数量被精确定义，数量在容器到容器之间不同；其中自由同位素选自麻醉药物、前药、盐、溶剂、水合物和多晶形，并且在分子中至少包含三种稳定同位素，所述稳定同位素选自13C、15N和18O，其标记度至少为95摩尔％；使用该检测试剂盒和一种定量测定麻醉药物的方法。
• Compounds for fluoroscense polarization immunoassays and immunoassays utilising them
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0597333A2

  公开（公告）日：1994-05-18

  Compounds of the formula wherein F is a fluorescing compound; Y is -NH- or a single covalent bond; Z is a straight or branched alkylene chain of 2 to 10 carbon atoms which is substituted by at least one hydrophilic group; Q is oxygen or sulfur; and X is a ligand-analog, the ligand-analog capable of being recognized by an antibody specific to the corresponding ligand. These compounds have improved properties in fluorescence polarization immunoassays by possessing either a better intensity and/or a larger span.

  式中的化合物 其中 F 是荧光化合物；Y 是-NH-或单个共价键；Z 是 2 至 10 个碳原子的直链或支链亚烷基链，至少被一个亲水基团取代；Q 是氧或硫；X 是配体类似物，配体类似物能够被相应配体的特异性抗体识别。这些化合物具有更好的强度和/或更大的跨度，从而改善了荧光偏振免疫分析的性能。
• Halogenated cannabinoid synthesis
  作者：Marcus A. Tius、G.S.Kamali Kannangara、Michael A. Kerr、Krista J.S. Grace

  DOI：10.1016/s0040-4020(01)90158-9

  日期：1993.4

  A convenient synthesis of several tricyclic and bicyclic fluoro- and iodo analogs of cannabinoids has been reported. A new, mild methodology for the synthesis of vinyl fluorides from vinylstannanes has also been demonstrated. These C9 halo-functionalized cannabinoid analogs, along with (-) and (+)-DELTA9-THC carboxylic acids, were screened for anti-inflammatory activity in the mouse ear edema assay. It was interesting Lo find that both enantiomers of DELTA9-THC carboxylic acid were moderately active as anti-inflammatories. The bicyclic vinyl iodide (18C) also showed appreciable anti-inflammatory activity.