1-hydroxy-3-pentyl-7,8-dihydrospiropyran-9,2'-<1,3>-dioxolan>-6(10H)-one | 6469-57-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 1-hydroxy-3-pentyl-7,8-dihydrospiropyran-9,2'-<1,3>-dioxolan>-6(10H)-one
• 英文别名: 7,8,9,10-Tetrahydro-1-hydroxy-3-pentyl-spiro<6H-dibenzopyran-9,2'-<1',3'>dioxolan>-6-on；7,8,9,10-Tetrahydro-1-hydroxy-3-pentyl-spiro(6H-dibenzopyran-9,2'-<1',3'>dioxolan)-6-on；1'-hydroxy-3'-pentylspiro[1,3-dioxolane-2,9'-8,10-dihydro-7H-benzo[c]chromene]-6'-one
• CAS: 6469-57-4
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: WZLXEGSFHHTMOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-hydroxy-3-pentyl-7,8-dihydrospiropyran-9,2'-<1,3>-dioxolan>-6(10H)-one 在 正丁基锂 、 氨 、 lithium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 49.55h， 生成 (+/-)-6,6-[2H6]dimethyl-11-nor-9-carboxy-Δ⁸-tetrahydrocannabinol
  参考文献：
  名称：

  Synthesis of [2H6]-labelled metabolites of cannabinoids

  摘要：

  Four [H-2(6)]-labelled metabolites of cannabinoids were synthesized for use as internal standards for GC/MS analysis. The hexadeutero-ketone 3, prepared from ketal 1, undergoes a Shapiro reaction to give (+/-)-6,6-[H-2(6)]dimethyl-11-nor-9-carboxy-Delta(9)-THC (4a) as the major product. The minor product, (+/-)-6,6-[H-2(6)] dimethyl-11-nor-9-carboxy-Delta(8)-THC (4b), was obtained after hydrolysis of its acetate methyl ester which was isolated using preparative HPLC. Reduction of 4a gave (+/-)-6,6-[H-2(6)]dimethyl-11-hydroxy-Delta(9)-THC (6). (+/-)-6,6-[H-2(6)]dimethyl-8 beta,11-dihydroxy-Delta(9)-THC (10), was also prepared from 3 using a reported procedure for the non-labelled analog.

  DOI：

  10.1002/1099-1344(200006)43:7<655::aid-jlcr350>3.0.co;2-t

文献信息

• Oxaphenanthrene Derivatives
  申请人：Taugerbeck Andreas

  公开号：US20080312224A1

  公开（公告）日：2008-12-18

  The invention relates to compounds of the formula (I), in which R 1 , R 2 , R 3 , R 4 , Y and A have the meanings indicated, and to processes for the preparation thereof and to the use thereof for the preparation of medicaments.

  本发明涉及式（I）的化合物，其中R1，R2，R3，R4，Y和A具有所示的含义，以及其制备方法和用于制备药物的使用。
• Hashish. 26. Factors influencing double-bond stability in cannabinoids
  作者：Haldean C. Dalzell、David B. Uliss、G. Richard Handrick、Raj K. Razdan

  DOI：10.1021/jo00318a021

  日期：1981.2
• DRIESSEN, R. A.;SALEMINK, C. A., REC. TRAV. CHIM. PAYS-BAS, 1982, 101, N 3, 95-96
  作者：DRIESSEN, R. A.、SALEMINK, C. A.

  DOI：——

  日期：——
• Driessen, R. A.; Salemink, C. A., Recueil des Travaux Chimiques des Pays-Bas, 1982, vol. 101, # 3, p. 95 - 96
  作者：Driessen, R. A.、Salemink, C. A.

  DOI：——

  日期：——
• US8133887B2
  申请人：——

  公开号：US8133887B2

  公开（公告）日：2012-03-13