3,5-dibromocyclopentene | 1890-04-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 3,5-dibromocyclopentene
• 英文别名: 3,5-Dibrom-1-cyclopenten；3,5-cis-dibromocyclopentene；1,4-dibromocyclopent-2-ene；3,5-Dibrom-cyclopenten
• CAS: 1890-04-6
• 化学式: C₅H₆Br₂
• 分子量: 225.911
• InChiKey: AKAJVSSDORNOIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,5-dibromocyclopentene 在 苄基三乙基氯化铵 、 potassium hydrogencarbonate 作用下， 以 甲醇 、 叔丁醇 为溶剂， 生成 环戊-2-烯-1,4-二醇
  参考文献：
  名称：

  Development of the Carbocyclic Nucleoside MDL 201449A:  A Tumor Necrosis Factor-α Inhibitor

  摘要：

  An efficient synthesis of (1S,4R)-(-)-4-tert-butyldimethylsilyloxy-2-cyclopentenyl acetate and (1R,4S)-(-)-4-tert-butyldimethylsilyloxy-2-cyclopentenol is described utilizing a furfuryl alcohol rearrangement, followed by a lithium aluminum hydride reduction with high facial selectivity and an efficient enzymatic resolution with pancreatin. Both of these intermediates were successfully utilized in the preparation of the carbocyclic nucleoside 9N-[(1'R,3'R)-trans-3'-hydroxycyclopentanyl]adenine hydrochloride, an agent which inhibits the formation of tumor necrosis factor-alpha.

  DOI：

  10.1021/op9701245
• 作为产物：
  描述：

  环戊二烯 在 溴 作用下， 以 氯仿 为溶剂， 以66%的产率得到3,5-dibromocyclopentene
  参考文献：
  名称：

  一种贝前列环素中间体的制备方法

  摘要：

  本发明公开一种贝前列环素中间体的制备方法，包括以下步骤：(1)环戊二烯的制备：取双环戊二烯加入BHT，加热到180‑200℃蒸馏，收集40‑50℃的馏分，收集完毕，进行第二次蒸馏，制备得到环戊二烯；(2)贝前列环素中间体的制备：将环戊二烯加入到溶剂A中，冷阱冷却降温至‑72℃后，用溶剂A稀释溴试剂，将溴试剂的溶剂A溶液缓慢滴加，控制温度在‑70℃，反应后，得到3,5‑二溴环戊烯；将2,4,6‑三溴苯酚溶解在无水溶剂B中，反应后，经后处理操作B制备得到贝前列环素中间体。采用本发明公开的制备方法，不仅有效降低了工艺生产过程中产生的杂质，提高了收率，且上述工艺绿色环保，降低了环保处理成本。

  公开号：

  CN111087284A

文献信息

• 5,6,7,-Trinor-4,8-inter-m-phenylene PGI.sub.2 derivatives and
  申请人：Toray Industries, Inc.

  公开号：US04564620A1

  公开（公告）日：1986-01-14

  Pharmaceutically useful compounds are 5,6,7-trinor-4,8-inter-m-phenylene PGI.sub.2 derivatives such as 5,6,7-trinor-4,8-inter-m-phenylene-13,14-didehydro PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-16,16-dimethyl PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-17-.alpha.-methyl-20-homo PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-17,18,19,20-tetranor-16-phenoxy PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-20-isopropylidene PGI.sub.2, 5,6,7-trinor-4,8-inter-(5-methyl-1,3-phenylene) PGI.sub.2, and 5,6,7-trinor-4,8-inter-m-phenylene-2,3-didehydro-16,17,18,19,20-pentanor-1 5-phenyl PGI.sub.2. They are useful in treatment of ulcers, thrombii and hypertension for example.

  药用化合物是5,6,7-三缺一-4,8-相间-间苯二酚 PGI.sub.2 衍生物，例如 5,6,7-三缺一-4,8-相间-间苯二酚-13,14-二去氢 PGI.sub.2，5,6,7-三缺一-4,8-相间-间苯二酚-16,16-二甲基 PGI.sub.2，5,6,7-三缺一-4,8-相间-间苯二酚-17-.alpha.-甲基-20-同源 PGI.sub.2，5,6,7-三缺一-4,8-相间-间苯二酚-17,18,19,20-四缺一-16-苯氧基 PGI.sub.2，5,6,7-三缺一-4,8-相间-间苯二酚-20-异丙亚甲基 PGI.sub.2，5,6,7-三缺一-4,8-相间-(5-甲基-1,3-苯基) PGI.sub.2，和 5,6,7-三缺一-4,8-相间-间苯二酚-2,3-二去氢-16,17,18,19,20-五缺一 5-苯基 PGI.sub.2。它们在治疗溃疡、血栓和高血压等方面具有用途。
• 5,6,7,-trinor-4,8-inter-m-phenylene 2-nor PGI.sub.2 derivatives and
  申请人：Toray Industries, Inc.

  公开号：US04822804A1

  公开（公告）日：1989-04-18

  Pharmaceutically useful compounds are 5,6,7-trinor-4,8-inter-m-phenylene PGI.sub.2 derivatives such as 5,6,7-trinor-4,8-inter-m-phenylene-2-nor-16,16-dimethyl PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-2-nor-17(S)-methyl PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-2-nor-17(R)-methyl PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-2-nor-16,16-dimethyl-.omega.-homo PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-2-nor-17(S)-methyl-.omega.-homo PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-2-nor-17(R)-methyl-.omega.-homo PGI.sub.2, 5,6, 7-trinor-4,8-inter-m-phenylene-2,17,18,19,20-pentanor-16,16-dimethyl-16-p ropoxy PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-2,18,19,20-tetranor-16,16-dimethyl-17-et ho xy PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-2,18,19,20-tetranor-16,16-dimethyl-17-pr op oxy PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-2,17,18,19,20-pentanor-16-phenoxy PGI.sub.2 and methyl esters thereof. 5,6,7-trinor-4,8-inter-m-phenylene-2,17,18,19,20-pentanor-16,16-dimethyl-16 -phenoxy PGI.sub.2 or its methyl ester, 5,6,7-trinor-4,8-inter-m-phenylene-2,17,18,19,20-pentanor-16-methyl-16-phe nox y PGI.sub.2 or its methyl ester. They are useful in treatment of ulcers, thrombii and hypertension for example.

  药用化合物是5,6,7-三去氢-4,8-间-m-苯撑PGI.sub.2衍生物，如5,6,7-三去氢-4,8-间-m-苯撑-2-去氢-16,16-二甲基PGI.sub.2，5,6,7-三去氢-4,8-间-m-苯撑-2-去氢-17(S)-甲基PGI.sub.2，5,6,7-三去氢-4,8-间-m-苯撑-2-去氢-17(R)-甲基PGI.sub.2，5,6,7-三去氢-4,8-间-m-苯撑-2-去氢-16,16-二甲基-ω-同系PGI.sub.2，5,6,7-三去氢-4,8-间-m-苯撑-2-去氢-17(S)-甲基-ω-同系PGI.sub.2，5,6,7-三去氢-4,8-间-m-苯撑-2-去氢-17(R)-甲基-ω-同系PGI.sub.2，5,6,7-三去氢-4,8-间-m-苯撑-2,17,18,19,20-五去氢-16,16-二甲基-16-丙氧基PGI.sub.2，5,6,7-三去氢-4,8-间-m-苯撑-2,18,19,20-四去氢-16,16-二甲基-17-乙氧基PGI.sub.2，5,6,7-三去氢-4,8-间-m-苯撑-2,18,19,20-四去氢-16,16-二甲基-17-丙氧基PGI.sub.2，5,6,7-三去氢-4,8-间-m-苯撑-2,17,18,19,20-五去氢-16-苯氧基PGI.sub.2及其甲酯。5,6,7-三去氢-4,8-间-m-苯撑-2,17,18,19,20-五去氢-16,16-二甲基-16-苯氧基PGI.sub.2或其甲酯，5,6,7-三去氢-4,8-间-m-苯撑-2,17,18,19,20-五去氢-16-甲基-16-苯氧基PGI.sub.2或其甲酯。它们可用于治疗溃疡、血栓和高血压等疾病。
• Process for the preparation of 1,4-diacetoxycyclopent-2-ene
  申请人：Teijin Limited

  公开号：US04001308A1

  公开（公告）日：1977-01-04

  A process for the preparation of 1,4-diacetoxycyclopent-2-ene, which comprises contacting a solution of 1,4-dibromocyclopent-2-ene in an inert organic solvent which is slightly soluble or insoluble in water, with an aqueous solution or suspension of at least one metal salt of acetic acid which is at least partially water-soluble, in the presence of a cationic surface-active compound.

  一种制备1,4-二乙酰氧基环戊-2-烯的过程，包括将1,4-二溴环戊-2-烯的溶液与一种惰性有机溶剂接触，该溶剂在水中略微溶解或不溶解，与至少一种乙酸金属盐的水溶液或悬浮液接触，该金属盐至少部分可溶于水，在阳离子表面活性剂的存在下进行。
• 一种贝前列素钠中间体的合成方法
  申请人：济南康和医药科技有限公司

  公开号：CN110452100A

  公开（公告）日：2019-11-15

  本发明涉及一种贝前列素钠中间体III的合成方法。以环戊烯和N‑溴代丁二酰亚胺(NBS)通过自由基反应得到二溴环戊烯，二溴环戊烯与2,4,6‑三溴苯酚相互作用直接以“一锅煮”法直接形成3,5‑双(2,4,6‑三溴苯氧基)环戊烯(化合物I)。再通过格氏反应得到化合物II和化合物III。且本发明采用N‑溴代丁二酰亚胺和商业化可获得的环戊烯为原料合成二溴环戊烯，避免了170℃裂解和‑30～‑40℃的超低温反应，同时避免了溴素的使用；反应条件更温和、环境更友好，便于工业化生产。
• The preparation of some pyridinium cyclopentadienylides
  作者：Douglas Lloyd、John S. Sneezum

  DOI：10.1016/0040-4020(58)80038-1

  日期：1958.1

  The preparation of some pyridinium cyclopentadienylides is described. A brief survey of earlier work in this field is included.

  描述了一些吡啶鎓环戊二烯化物的制备。其中包括对该领域早期工作的简要概述。

表征谱图