(E)-5-Bromo-pent-3-enoic acid methyl ester | 81166-22-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-5-Bromo-pent-3-enoic acid methyl ester
• 英文别名: Methyl 5-bromopent-3-enoate；methyl (E)-5-bromopent-3-enoate
• CAS: 81166-22-5
• 化学式: C₆H₉BrO₂
• 分子量: 193.04
• InChiKey: YTBXNIPJPAPVPW-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-5-Bromo-pent-3-enoic acid methyl ester 在 盐酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (E)-5-(6,7-Dichloro-2-cyclopentyl-2-methyl-1-oxo-indan-5-yloxy)-pent-3-enoic acid
  参考文献：
  名称：

  Agents for the treatment of brain injury. 1. (Aryloxy)alkanoic acids

  摘要：

  Blunt and ischemic injuries of the brain have been shown to result in swelling that is predominantly limited to a single cell type, the astrocyte, within the complex cellular mosiac of cerebral gray matter. Evaluation of various diuretic (aryloxy)acetic acids in vitro using incubating cat brain slices and primary astrocyte cultures identified compounds with marked ability to inhibit brain tissue swelling. Some of the compounds significantly reduced the mortality and morbidity following acceleration/deceleration brain injury in anesthesized cats. A variety of (indanyloxy)alkanoic acids were synthesized which were analogous to the dually active (indanyloxy)acetic acids. Some of the 4-(indanyloxy)butanoic acids were found to be devoid of diuretic activity but to possess equal or greater activity than the dually active compounds in the in vitro and in vivo brain assays. Selected examples from both the (indanyloxy)acetic and 4-(indanyloxy)butanoic acid series showed marked chiral effects, with one enantiomer generally exhibiting a much greater activity than the other. A clinical study of severely head-injured patients treated with ethacrynic acid demonstrated a significantly improved outcome when compared to controls. These data suggest a clinical advantage for the nondiuretic (aryloxy)alkanoic acids which possess in vitro and in vivo activities in the cat brain assays that are comparable or superior to dually active compounds.

  DOI：

  10.1021/jm00347a017

文献信息

• DBU-catalyzed Michael additions of bulky glycine imine to β-arylfuryl substituted α,β-unsaturated esters
  作者：Mei-Ling Cheng、Xue-Ying Wang、Yu-Jun Bai、Si-Kai Zhu、Sheng-Yong Zhang、Guo-Qiang Bao、Ping-An Wang

  DOI：10.1080/00397911.2023.2240450

  日期：2023.10.2

  Abstract DBU-catalyzed Michael reactions between tert-butyl 2-((diphenylmethylene) amino)acetate and simple β-substituted α,β-unsaturated esters have been achieved in high yields (up to 95% yield) and diastereoselectivties (up to 99:1 dr) in the presence of 1.0 eq. of LiBr in acetonitrile under room temperature. The Michael adduct can be easily converted into trans-3-substituted pyroglutamic acid ester

  摘要 DBU 催化的2-((二苯基亚甲基)氨基)乙酸叔丁酯和简单的 β-取代 α,β-不饱和酯之间的 Michael 反应已实现高产率（高达 95% 的产率）和非对映选择性（高达 99: 1 dr) 在 1.0 eq 存在的情况下 室温下溴化锂在乙腈中的溶液。通过内酰胺化后的原位酸性水解，迈克尔加合物可以很容易地转化为反式-3-取代的焦谷氨酸酯。
• CRAGOE, E. J. ,, JR;GOULD, N. P.;WOLTERSDORF, O. W. ,, JR;ZIEGLER, C., J. MED. CHEM., 1982, 25, N 5, 567-579
  作者：CRAGOE, E. J. ,, JR、GOULD, N. P.、WOLTERSDORF, O. W. ,, JR、ZIEGLER, C.

  DOI：——

  日期：——
• GEVORKYAN, A. A.;KAZARYAN, P. I.;AVAKYAN, S. V., ZH. ORGAN. XIMII, 24,(1988) N 6, 1340-1341
  作者：GEVORKYAN, A. A.、KAZARYAN, P. I.、AVAKYAN, S. V.

  DOI：——

  日期：——
• AMINOPYRIDAZINONE COMPOUNDS AS PROTEIN KINASE INHIBITORS
  申请人：ETERNITY BIOSCIENCE INC.

  公开号：US20170152264A1

  公开（公告）日：2017-06-01

  The present disclosure provides a compound of formula (I) and the use thereof for the therapeutic treatment of human cancers including B-cell lymphoma and autoimmune diseases such as rheumatoid arthritis, systemic lupus erythematosus, and multiple sclerosis.
• US3987081A
  申请人：——

  公开号：US3987081A

  公开（公告）日：1976-10-19