(+/-)-N-trifluoroacetyldomesticine | 71046-76-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: (+/-)-N-trifluoroacetyldomesticine
• 英文别名: N-trifluoroacetylnordomesticine；2,2,2-trifluoro-1-(19-hydroxy-18-methoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaen-13-yl)ethanone
• CAS: 71046-76-9
• 化学式: C₂₀H₁₆F₃NO₅
• 分子量: 407.346
• InChiKey: TWILEBCABUCERK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  68.23
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+/-)-N-trifluoroacetyldomesticine 在 sodium hydride 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (+/-)-Nornantenine
  参考文献：
  名称：

  Structure–activity relationship studies with (±)-nantenine derivatives for α1-adrenoceptor antagonist activity

  摘要：

  A series of (+/-)-nantenine derivatives of the natural aporphine alkaloids was synthesized and examined for a blocking action on a, adrenoceptors in rat aorta and A10-cells. The potency of these derivatives was compared with that of an aporphine-related compounds (+)boldine, an alpha(1)-adrenoceptor antagonist. Among nine (+/-)-nantenine derivatives having different substituents at N-6, C-1, or C-4 of the aporphine skeleton, (+/-)-domesticine had the most powerful ot alpha(1) -adrenoceptor-blocking action. The order of pA(2) values was (+/-)-domesticine (8.06 +/- 0.06)>(+/-)-nordomesticine (7.34 +/- 0.03)>(+/-)-nantenine(7.03 +/- 0.03)>(+)-boldine(6.91 +/- 0.02)> other derivatives. Study of the structure -activity relationships showed that the replacement of a methoxy moiety at C-1 position of (+/-)-nantenine with a hydroxyl group increased affinity for the receptor. In contrast, replacement of a methyl group with a hydrogen atom or an ethyl group at N-6 position in the (+/-)-nantenine structure decreased affinity for the receptor. These results suggest that a hydroxyl group at the C-1 position and a methyl group at the N-6 position in the (+/-)-nantenine structure are essential for the enhancement of affinity for the alpha(1)-adrenoceptor. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0014-2999(02)01303-1
• 作为产物：
  描述：

  1-benzo[1,3]dioxol-5-ylmethyl-7-benzyloxy-6-methoxy-1,2,3,4-tetrahydro-isoquinoline 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 5.5h， 生成 (+/-)-N-trifluoroacetyldomesticine
  参考文献：
  名称：

  Formation and Reaction of p-Quinol Acetates of N-Trifluoroacetyltetrahydroisoqunolin-7-ols

  摘要：

  Lead tetraacetate oxidation of N-trifluoroacetyltetrahydroisoquinolin-7-ols (13a, b) in AcOH gave stable p-quinol acetates (17a, b). Reaction of 17 with trifluoroacetic acid in CH2Cl2 or MeCN gave morphinandienones (15) and aporphines (16), respectively. In contrast with o-quinol acetates (14), it was found that reaction of p-quinol acetates (17) in MeCN was considerably slower than that in CH2Cl2. A mechanistic pathway on the reaction is deduced.

  DOI：

  10.3987/com-92-s(t)95

文献信息

• ——
  作者：

  DOI：——

  日期：——
• Hoshino, Osamu; Ogasawara, Hiromichi; Suzuki, Masaji, Heterocycles, 1987, vol. 25, p. 151 - 153
  作者：Hoshino, Osamu、Ogasawara, Hiromichi、Suzuki, Masaji、Umezawa, Bunsuke

  DOI：——

  日期：——
• Ogasawara, Hiromichi; Suzuki, Masaji; Shiohara, Tomohiro, Heterocycles, 1998, vol. 47, # 2, p. 911 - 919
  作者：Ogasawara, Hiromichi、Suzuki, Masaji、Shiohara, Tomohiro、Hoshino, Osamu

  DOI：——

  日期：——