2-(2-bromoacetyl)phenyl ethyl carbonate | 519753-07-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-bromoacetyl)phenyl ethyl carbonate
• 英文别名: [2-(2-Bromoacetyl)phenyl] ethyl carbonate
• CAS: 519753-07-2
• 化学式: C₁₁H₁₁BrO₄
• 分子量: 287.11
• InChiKey: FYRKTZSWXYIJND-UHFFFAOYSA-N

物化性质

• 沸点：
  362.2±38.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二氢罂粟碱盐酸盐 、 2-(2-bromoacetyl)phenyl ethyl carbonate 在 碳酸氢钠 作用下， 以 乙腈 为溶剂， 生成 2-[1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]phenyl ethyl carbonate
  参考文献：
  名称：

  Further developments in the synthesis of lamellarin alkaloids via direct metal–halogen exchange

  摘要：

  Direct metal-halogen exchange of 2-bromopyrrole carbonate derivatives with tert-butyllithium followed by the intramolecular lactonization of the resulting 2-pyrrole anion onto the carbonate provided the corresponding lamellarins in moderate to good yield. The lamellarin framework could be obtained from the direct metal-halogen exchange strategy in a 26-33% overall yield over 5-6 steps. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02887-3
• 作为产物：
  描述：

  O-Ethoxycarbonyl-o-acetylphenol 在 benzyltrimethylazanium tribroman-2-uide 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到2-(2-bromoacetyl)phenyl ethyl carbonate
  参考文献：
  名称：

  Further developments in the synthesis of lamellarin alkaloids via direct metal–halogen exchange

  摘要：

  Direct metal-halogen exchange of 2-bromopyrrole carbonate derivatives with tert-butyllithium followed by the intramolecular lactonization of the resulting 2-pyrrole anion onto the carbonate provided the corresponding lamellarins in moderate to good yield. The lamellarin framework could be obtained from the direct metal-halogen exchange strategy in a 26-33% overall yield over 5-6 steps. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02887-3

文献信息

• Phenoxy derivatives, their preparation, and pharmaceutical compositions containing them
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP0130077A2

  公开（公告）日：1985-01-02

  A phenoxy compound represented by general formula (I), or a salt thereof wherein: A is an imidazolyl group, a pyridyl group, a pyridyloxy group, an oxo-substituted chromenyloxy group, a C1-C5 alkyl group, an amino group which may be substituted with a phenyl group or a C1-C5 alkyl group, or a carbamoyl group substituted with a cyclohexylamino group or an imidazolylalkyl group; B is a single bond, a thiazolyl group which may be substituted with a C1-C5 alkyl group, a group represented by formula: -(CH2)n-O-,-(CH2)nCONH(CH2)k-or-(CH2)n-N(R4)-wherein k is 0 or an integer of 1 to 5, n is an integer of 1 to 6 and R4 is a C1-C5 alkyl group; m is 0 or an integer of 1 to 6; R' is a hydroxyl group, an amino group ora C1-C5 alkoxy group; and R2 and R' are the same or different and selected from a hydrogen atom and C,-C5 alkyl groups. The compounds are effective for prophylaxis and treatment of arteriosclerosis, cerebal infraction, transient ischemic attack, angina pectoris, peripheral thrombus and obstruction.

  通式(I)代表的苯氧基化合物或其盐 其中 A 是咪唑基、吡啶基、吡啶氧基、氧代色原氧基、C1-C5 烷基、可被苯基或 C1-C5 烷基取代的氨基、或被环己基氨基或咪唑烷基取代的氨基甲酰基； B 是单键、可被 C1-C5 烷基取代的噻唑基、由式表示的基团：-(CH2)n-O-、-(CH2)nCONH(CH2)k-或-(CH2)n-N(R4)-其中 k 为 0 或 1 至 5 的整数，n 为 1 至 6 的整数，R4 为 C1-C5 烷基； m 为 0 或 1 至 6 的整数； R' 是羟基、氨基或 C1-C5 烷氧基；以及 R2 和 R'相同或不同，选自氢原子和 C,-C5烷基。 这些化合物可有效预防和治疗动脉硬化、脑梗塞、短暂性脑缺血发作、心绞痛、外周血栓和阻塞。
• Utility of Polymer-Supported Reagents in the Total Synthesis of Lamellarins
  作者：Poonsakdi Ploypradith、Rachel Kirk Kagan、Somsak Ruchirawat

  DOI：10.1021/jo050388m

  日期：2005.6.1

  Four solid-supported reagents have been utilized in the multistep synthesis of lamellarins. The use of Amberlyst A-26 Br-3(-) and polymer bound pyridine hydrobromide perbromide (PVPHP) for keto alpha-bromination of the less studied ortho-substituted acetophenone derivatives selectively furnished the corresponding monobromination products (phenacyl bromide derivatives), which were used directly in condensation reactions with benzyldihydroisoquinoline mediated by Amberlyst A-26 NaCO3-. The 2H-pyrrole carbonates subsequently underwent intramolecular Friedel-Crafts transacylation followed by lactonization to provide the lamellarin skeleton. Alternatively, Amberlyst A-26 NaCO3- effectively served as base in condensation reaction of benzyldihydroisoquinoline with alpha-nitrocinnamate derivatives to provide the corresponding 2-ethoxycarbonyl pyrroles, which smoothly underwent O-debenzylation reaction followed by lactonization to furnish the lamellarin skeleton. The novel Amberlyst-15 mediated lactonization reactions effectively combined the otherwise two separate steps into a single transformation.
• US4794113A
  申请人：——

  公开号：US4794113A

  公开（公告）日：1988-12-27
• US4795753A
  申请人：——

  公开号：US4795753A

  公开（公告）日：1989-01-03
• US4798838A
  申请人：——

  公开号：US4798838A

  公开（公告）日：1989-01-17