5-O-acetyldihydrolycopodine | 52998-89-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5-O-acetyldihydrolycopodine
• 英文别名: β-acetyldihydrolycopodine；(16R)-5β-acetoxy-16-methyl-lycopodane；(16R)-5β-Acetoxy-16-methyl-lycopodan；[(1R,2R,10S,11R,13S,15R)-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-yl] acetate
• CAS: 52998-89-7
• 化学式: C₁₈H₂₉NO₂
• 分子量: 291.434
• InChiKey: SZELUKCBWALJTL-PCCLBNHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-O-acetyldihydrolycopodine 在 偶氮二异丁腈 、 碘苯二乙酸 、 碘 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成
  参考文献：
  名称：

  PIDA/I₂-Mediated α- and β-C(sp³)–H Bond Dual Functionalization of Tertiary Amines

  摘要：

  The alpha,beta-C(sp(3))-H bond dual functionalization of tertiary amines is still a challenging task for both organic and medicinal chemists. Herein a direct, mild, metal-free, and site-specific method mediated by PIDA/I-2 was developed for alpha,beta-C(sp(3))-H bond dual functionalization of tertiary amines, and this method can provide facile access to alpha-keto lactams or rarely studied alpha,alpha-diiodo lactams. Moreover, this method was used for the effective syntheses of three natural products [obscurumine C (13), obscurumine O (17), and strychnocarpine (18)] and direct preparation of mimics of the in vivo metabolites of two FDA-approved drugs (imatinib and donepezil) in 36-60% overall yield. The method represents a promising protocol for the late-stage alpha,beta-C(sp(3))-H bond oxidative dual functionalization of tertiary amine-containing drugs and complex natural products.

  DOI：

  10.1021/acs.joc.8b01424
• 作为产物：
  描述：

  石松鹼 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 5-O-acetyldihydrolycopodine
  参考文献：
  名称：

  PIDA/I₂-Mediated α- and β-C(sp³)–H Bond Dual Functionalization of Tertiary Amines

  摘要：

  The alpha,beta-C(sp(3))-H bond dual functionalization of tertiary amines is still a challenging task for both organic and medicinal chemists. Herein a direct, mild, metal-free, and site-specific method mediated by PIDA/I-2 was developed for alpha,beta-C(sp(3))-H bond dual functionalization of tertiary amines, and this method can provide facile access to alpha-keto lactams or rarely studied alpha,alpha-diiodo lactams. Moreover, this method was used for the effective syntheses of three natural products [obscurumine C (13), obscurumine O (17), and strychnocarpine (18)] and direct preparation of mimics of the in vivo metabolites of two FDA-approved drugs (imatinib and donepezil) in 36-60% overall yield. The method represents a promising protocol for the late-stage alpha,beta-C(sp(3))-H bond oxidative dual functionalization of tertiary amine-containing drugs and complex natural products.

  DOI：

  10.1021/acs.joc.8b01424

文献信息

• THE ALKALOIDS OF <i>LYCOPODIUM</i> SPECIES: XII. RELATIONSHIP BETWEEN SOME OF THE MINOR ALKALOIDS AND LYCOPODINE
  作者：Bryce Douglas、D. G. Lewis、Léo Marion

  DOI：10.1139/v53-038

  日期：1953.3.1

  Reduction of the carbonyl group of lycopodine with lithium aluminum hydride gives rise to dihydrolycopodine which contains a secondary alcoholic group. The new base can be dehydrated to form anhydrodihydrolycopodine and this is identical with alkaloid L14(C₁₆H₂₅N). Acetylation of dihydrolycopodine produces O-acetyldihydrolycopodine which is identical with alkaloid L2(C₁₈H₂₉O₂N). On distillation at atmospheric pressure alkaloid L2 is pyrolyzed and gives rise to 7-methylquinoline. Alkaloids L8 and L30 which had been reported previously as different have now been found to be identical.

  用铝锂氢化物还原石松碱的羰基，得到含有次级醇基的二氢石松碱。这种新碱可以脱水形成无水二氢石松碱，它与L14（C16H25N）生物碱相同。对二氢石松碱进行乙酰化可以产生O-乙酰基二氢石松碱，它与L2（C18H29O2N）生物碱相同。在大气压下蒸馏碱L2会热解，产生7-甲基喹啉。先前报告的L8和L30生物碱被发现是相同的。
• Kubota, Takaaki; Yahata, Hiroko; Ishiuchi, Kan'ichiro, Heterocycles, 2007, vol. 74, # C, p. 843 - 848
  作者：Kubota, Takaaki、Yahata, Hiroko、Ishiuchi, Kan'ichiro、Obara, Yutaro、Nakahat, Norimichi、Kobayashi, Jun'ichi

  DOI：——

  日期：——
• PIDA/I₂-Mediated α- and β-C(sp³)–H Bond Dual Functionalization of Tertiary Amines
  作者：Yu Zhu、Li-Dong Shao、Zhen-Tao Deng、Ying Bao、Xin Shi、Qin-Shi Zhao

  DOI：10.1021/acs.joc.8b01424

  日期：2018.9.7

  The alpha,beta-C(sp(3))-H bond dual functionalization of tertiary amines is still a challenging task for both organic and medicinal chemists. Herein a direct, mild, metal-free, and site-specific method mediated by PIDA/I-2 was developed for alpha,beta-C(sp(3))-H bond dual functionalization of tertiary amines, and this method can provide facile access to alpha-keto lactams or rarely studied alpha,alpha-diiodo lactams. Moreover, this method was used for the effective syntheses of three natural products [obscurumine C (13), obscurumine O (17), and strychnocarpine (18)] and direct preparation of mimics of the in vivo metabolites of two FDA-approved drugs (imatinib and donepezil) in 36-60% overall yield. The method represents a promising protocol for the late-stage alpha,beta-C(sp(3))-H bond oxidative dual functionalization of tertiary amine-containing drugs and complex natural products.