4-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-4-ethyl morpholinium bromide | 92641-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-4-ethyl morpholinium bromide
• 英文别名: 4-Ethyl-4-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-morpholinium bromide；3-(4-ethylmorpholin-4-ium-4-yl)-3H-2-benzofuran-1-one;bromide
• CAS: 92641-16-2
• 化学式: Br*C₁₄H₁₈NO₃
• 分子量: 328.206
• InChiKey: BQQSOZWCNZKRNB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.27
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-溴苯酞 在 N-乙基吗啉 作用下， 以 乙腈 为溶剂， 以72%的产率得到4-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-4-ethyl morpholinium bromide
  参考文献：
  名称：

  Production of 1-phthalidyl-5-fluorouracil derivatives

  摘要：

  生产抗肿瘤药物1-邻苯二甲酰基-5-氟尿嘧啶衍生物的高选择性和高产率过程，包括将邻苯二甲酰基化合物(II)与胺(III)反应，生成季铵盐(IV)，然后将后者与5-氟尿嘧啶反应。[其中X是离去基团；##STR2##是三乙胺、N-甲基吗啉、N-乙基吗啉等；R.sup.4和R.sup.5分别是氢、三烷基硅氧基、烷氧基、硝基、氰基、羧基或烷氧羰基]。

  公开号：

  US04605738A1

文献信息

• Studies of antitumor-active 5-fluorouracil derivatives. I. Synthesis of N-phthalidyl 5-fluorouracil derivatives.
  作者：SUSUMU KAMATA、NOBUHIRO HAGA、TAKEAKI MATSUI、WATARU NAGATA

  DOI：10.1248/cpb.33.3160

  日期：——

  Several 5-fluorouracil derivatives in which the phthalidyl (1, 3-dihydro-3-oxoisobenzofuran-1-yl) group, appropriately substituted on its benzene ring, is substituted at the N (1)-or N (3)-position or at both positions were synthesized, and their antitumor activities were evaluated. Among these compounds, 1-(1, 3-dihydro-3-oxoisobenzofuran-1-yl)-5-fluorouracil (3a, 590-S) was shown to be markedly active against several experimental tumor systems. Several methods for a simple and efficient large-scale preparation of 3a were examined. The large-scale preparation of 3a was effected most efficiently by the condensation of 5-fluorouracil with the quaternary ammonium salt of 3-bromophthalide in the presence of a base. The synthesis of (+)- and (-)-3a is also described.

  合成了几种5-氟尿嘧啶衍生物，其中苯并二氢呋喃酮（1,3-二氢-3-氧异苯并呋喃-1-基）基团在其苯环上适当取代，并在N(1)或N(3)位或两个位置上进行取代，并评估了它们的抗肿瘤活性。在这些化合物中，1-(1,3-二氢-3-氧异苯并呋喃-1-基)-5-氟尿嘧啶（3a，590-S）显示出对几种实验性肿瘤系统有显著的活性。研究了几种简单高效的3a大规模制备方法。通过5-氟尿嘧啶与3-溴邻苯二甲酰亚胺的季铵盐在碱存在下缩合，最有效地实现了3a的大规模制备。还描述了(+)-和(-)-3a的合成。
• Phthalidylammonium compounds and their production, and their use in the production of 1-phthalidyl-5-fluorouracil derivatives and formulations containing such derivatives
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0112067A2

  公开（公告）日：1984-06-27

  Novel phthalidylammonium compounds (IV) are intermediates in a highly selective and high yield process for producing 1-phthalidyl-5-fluorouracil derivatives of formula (I) which are antitumour agents. The process comprises reacting a phthalidyl compound (II) with an amine (III) to yield the quaternary ammonium salts (IV), and then reacting the latter with 5-fluorouracil as follows: in which X is a leaving group; R1, R2 and R3 each independently represents alkyl or R' represents alkyl and R2 and R3 taken together with the adjacent nitrogen atom form a saturated 5- or 6-membered ring which may contain oxygen or represents quinuclidine; and R4 and R5 each independently represents hydrogen, trialkylsilyloxy, alkoxy, nitro, cyano, carboxy or alkoxycarbonyl.

  新型酞铵化合物（IV）是一种高选择性和高产率工艺的中间体，可用于生产抗肿瘤剂式（I）的 1-酞酰基-5-氟尿嘧啶衍生物。该工艺包括将邻苯二甲酰基化合物（II）与胺（III）反应生成季铵盐（IV），然后将后者与 5-氟尿嘧啶反应如下： 其中 X 是离去基团；R1、R2 和 R3 各自独立地代表烷基或 R' 代表烷基，R2 和 R3 与相邻的氮原子一起形成饱和的 5 或 6 元环，该环可能含有氧或 代表奎宁环；以及 R4 和 R5 各自独立地代表氢、三烷基硅氧基、烷氧基、硝基、氰基、羧基或烷氧羰基。
• KAMATA, SUSUMU;XAGA, NOBUXIRO;NAGATO, SEHN;MATSUI, TAKEHAKI
  作者：KAMATA, SUSUMU、XAGA, NOBUXIRO、NAGATO, SEHN、MATSUI, TAKEHAKI

  DOI：——

  日期：——
• US4605738A
  申请人：——

  公开号：US4605738A

  公开（公告）日：1986-08-12
• Production of 1-phthalidyl-5-fluorouracil derivatives
  申请人：Shionogi & Co., Ltd.

  公开号：US04605738A1

  公开（公告）日：1986-08-12

  Highly selective and high yield process for producing antitumor agent 1-phthalidyl-5-fluorouracil derivatives of formula (I) which comprises reacting a phthalidyl compound (II) with an amine (III) to yield the quaternary ammonium salts (IV), and reacting the latter with 5-fluorouracil. ##STR1## [wherein X is leaving group; ##STR2## is triethylamine, N-methylmorpholine, N-ethylmorpholine, and the like; R.sup.4 and R.sup.5 each is hydrogen, trialkylsilyloxy, alkoxy, nitro, cyano, carboxy, or alkoxycarbonyl].

  生产抗肿瘤药物1-邻苯二甲酰基-5-氟尿嘧啶衍生物的高选择性和高产率过程，包括将邻苯二甲酰基化合物(II)与胺(III)反应，生成季铵盐(IV)，然后将后者与5-氟尿嘧啶反应。[其中X是离去基团；##STR2##是三乙胺、N-甲基吗啉、N-乙基吗啉等；R.sup.4和R.sup.5分别是氢、三烷基硅氧基、烷氧基、硝基、氰基、羧基或烷氧羰基]。