7-bromo-9-bromomethyl-2,3-dihydro[1,4]dioxino[2,3-g]quinoline-8-carboxylic acid ethyl ester hydrobromic ester salt

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-bromo-9-bromomethyl-2,3-dihydro[1,4]dioxino[2,3-g]quinoline-8-carboxylic acid ethyl ester hydrobromic ester salt
• 英文别名: 7-bromo-9-bromomethyl-2,3-dihydro[1,4]dioxino[2,3-g]quinoline-8-carboxylic acid ethyl ester hydrobromic acid salt；7-Bromo-9-bromomethyl-2,3-dihydro[1,4]dioxino[2,3-g]quinoline-8-carboxylic acid ethyl ester hydrobromic acid salt；ethyl 7-bromo-9-(bromomethyl)-2,3-dihydro-[1,4]dioxino[2,3-g]quinoline-8-carboxylate;hydrobromide
• 化学式: BrH*C₁₅H₁₃Br₂NO₄
• 分子量: 511.992
• InChiKey: OKKOAYCJNFPKAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-bromo-9-bromomethyl-2,3-dihydro[1,4]dioxino[2,3-g]quinoline-8-carboxylic acid ethyl ester hydrobromic ester salt 在 palladium diacetate 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 13.33h， 生成 勒托替康
  参考文献：
  名称：

  Convergent catalytic asymmetric synthesis of camptothecin analog GI147211C

  摘要：

  The topoisomerase I inhibitor G1147211C (4) was discovered at Glare Wellcome and shown to have promising anti-cancer properties. In order to fully assess the clinical potential of 3, an improved synthesis of the: drug substance was required. Herein is described a convergent catalytic asymmetric synthesis of 4 which utilizes as key steps, two Heck reactions, a Sharpless asymmetric dihydroxylation reaction, and a Mitsunobu reaction. A 2-chloroquinoline is shown to be a viable substrate for the final Heck reaction to generate the camptothecin nucleus. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00357-8
• 作为产物：
  描述：

  9-chloromethyl-7-oxo-2,3,6,7-tetrahydro[1,4]dioxino[2,3-g]quinoline-8-carboxylic acid ethyl ester 在 三溴氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.5h， 以84%的产率得到7-bromo-9-bromomethyl-2,3-dihydro[1,4]dioxino[2,3-g]quinoline-8-carboxylic acid ethyl ester hydrobromic ester salt
  参考文献：
  名称：

  Convergent catalytic asymmetric synthesis of camptothecin analog GI147211C

  摘要：

  The topoisomerase I inhibitor G1147211C (4) was discovered at Glare Wellcome and shown to have promising anti-cancer properties. In order to fully assess the clinical potential of 3, an improved synthesis of the: drug substance was required. Herein is described a convergent catalytic asymmetric synthesis of 4 which utilizes as key steps, two Heck reactions, a Sharpless asymmetric dihydroxylation reaction, and a Mitsunobu reaction. A 2-chloroquinoline is shown to be a viable substrate for the final Heck reaction to generate the camptothecin nucleus. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00357-8

文献信息

• Method of removing heavy metal contaminants from organic compounds
  申请人：Glaxo Wellcome, Inc.

  公开号：US05840898A1

  公开（公告）日：1998-11-24

  A process for removal of heavy metal contaminants from organic compounds, especially campthothecin analogs.

  一种用于从有机化合物中去除重金属污染物的过程，特别是用于去除喜树碱类似物中的重金属。
• INTERMEDIATES IN PHARMACEUTICAL CAMPTOTHECIN PREPARATION
  申请人：GLAXO WELLCOME INC.

  公开号：EP0758333A1

  公开（公告）日：1997-02-19
• [EN] INTERMEDIATES IN PHARMACEUTICAL CAMPTOTHECIN PREPARATION<br/>[FR] INTERMEDIAIRES UTILISES DANS LA PREPARATION PHARMACEUTIQUE DE LA CAMPTOTHECINE
  申请人：——

  公开号：WO1995029917A2

  公开（公告）日：1995-11-09

  [EN] A process of providing novel compounds of Formula (I), which are useful as intermediates in the preparation of camptothecin and camptothecin-like compounds, wherein: R<1> represents alkyl, particularly methyl, R<2> represents H or alkyl, particularly methyl, R<3> represents H or alkyl, particularly H; Q represents triflate or halo particularly bromo and iodo more particularly iodo and Y represents chloro or OR<4>, wherein R<4> represents alkyl or triflate, or particularly H.
  [FR] Procédé d'obtention de nouveaux composés de formule (I) servant d'intermédiaires dans la préparation de la camptothécine ou de composés analogues. Dans ladite formule, R<1> représente alkyle, particulièrement méthyle, R<2> représente H ou alkyle, particulièrement méthyle, R<3> représente H ou alkyle, particulièrement H, Q représente triflate ou halo, particulièrement bromo et iodo et plus particulièrement iodo, et Y représente chloro ou OR<4>, où R<4> représente alkyle ou triflate ou plus particulièrement H.
• Convergent catalytic asymmetric synthesis of camptothecin analog GI147211C
  作者：Francis G. Fang、Donald D. Bankston、Edward M. Huie、M. Ross Johnson、Myung-Chol Kang、Craig S. LeHoullier、George C. Lewis、Thomas C. Lovelace、Melissa W. Lowery、Darryl L. McDougald、Clive A. Meerholz、John J. Partridge、Matthew J. Sharp、Shiping Xie

  DOI：10.1016/s0040-4020(97)00357-8

  日期：1997.8

  The topoisomerase I inhibitor G1147211C (4) was discovered at Glare Wellcome and shown to have promising anti-cancer properties. In order to fully assess the clinical potential of 3, an improved synthesis of the: drug substance was required. Herein is described a convergent catalytic asymmetric synthesis of 4 which utilizes as key steps, two Heck reactions, a Sharpless asymmetric dihydroxylation reaction, and a Mitsunobu reaction. A 2-chloroquinoline is shown to be a viable substrate for the final Heck reaction to generate the camptothecin nucleus. (C) 1997 Elsevier Science Ltd.