5-bromo-pent-3t-en-1-yne | 26122-94-1

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 5-bromo-pent-3t-en-1-yne
• 英文别名: 5-Brom-pent-3t-en-1-in；(E)-5-bromopent-3-en-1-yne
• CAS: 26122-94-1
• 化学式: C₅H₅Br
• 分子量: 144.999
• InChiKey: DTEFNNCAKDJTRT-ONEGZZNKSA-N

物化性质

• 沸点：
  92-100 °C(Press: 16 Torr)
• 密度：
  1.44 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  5-bromo-pent-3t-en-1-yne 生成 (+/-)-trans-2,10-Dihydroxy-decen-(4)-diin-(6,8)-saeure
  参考文献：
  名称：

  Cambie,R.C. et al., Journal of the Chemical Society, 1963, p. 3466 - 3468

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-2-penten-4-yn-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 乙腈 为溶剂， 生成 5-bromo-pent-3t-en-1-yne
  参考文献：
  名称：

  化学酶后期修饰实现下游点击介导的肽荧光标记

  摘要：

  用 22 种非天然焦磷酸盐筛选了 N1-色氨酸异戊二烯基转移酶 AcyF 的混杂性，这些焦磷酸盐表现出适合铜催化叠氮-炔环加成、复分解和逆电子需求 Diels-Alder (IEDDA) 反应的反应基团。 AcyF 定制了含有色氨酸的 10 聚体大环肽，并通过 IEDDA 成功地用四嗪-荧光素缀合物标记了所得修饰肽。

  DOI：

  10.1002/anie.202215979

文献信息

• Synthetic Studies of the Derivatives of Acetylene. I. Reactions of 5-Bromopent-3-en-1-yne
  作者：Kikumasa Sato、Masao Hirayama

  DOI：10.1246/bcsj.42.2589

  日期：1969.9

  The preparation of pent-2-en-4-ynylamine and pent-2-en-4-ynylthiol and their derivatives from 5-bromopent-3-en-1-yne was studied. Moreover, in connection with the preparation of the bromide, the rearrangement-bromination of vinylethynylcarbinol was found to give three isomeric bromides, 5-bromopent-trans-3-en-1-yne, 5-bromopent-cis-3-en-1-yne, and 3-bromopent-1-en-4-yne. Pent-2-en-4-ynylamine was obtained

  研究了从 5-溴戊-3-烯-1-炔制备戊-2-烯-4-炔胺和戊-2-烯-4-炔硫醇及其衍生物。此外，关于溴化物的制备，发现乙烯基乙炔基甲醇的重排-溴化得到三种异构的溴化物，5-溴戊-反式-3-en-1-yne，5-溴戊-顺-3-en-1 -yne 和 3-bromopent-1-en-4-yne。Pent-2-en-4-ynylamine 由 5-bromopent-3-en-1-yne 通过两种方法获得，即六胺盐的水解和 N-(pent-2-en-4-炔基）邻苯二甲酰亚胺。5-溴戊-3-烯-1-炔与氢硫化钾反应，用醇氨分解戊-2-烯-4-炔基黄原酸乙酯，得到戊-2-烯-4-炔硫醇。
• Design and Synthesis of m1-Selective Muscarinic Agonists:  (<i>R</i>)-(−)-(<i>Z</i>)-1-Azabicyclo[2.2.1]heptan-3-one, <i>O</i>-(3-(3‘-Methoxyphenyl)-2-propynyl)- oxime Maleate (CI<b>-</b>1017), a Functionally m1-Selective Muscarinic Agonist
  作者：Haile Tecle、Stephen D. Barrett、David J. Lauffer、Corinne Augelli-Szafran、Mark R. Brann、Michael J. Callahan、Bradley. W. Caprathe、Robert E. Davis、Patricia D. Doyle、David Eubanks、William Lipiniski、Tara Mirzadegan、Walter H. Moos、D. W. Moreland、Carrie B. Nelson、Michael R. Pavia、Charlotte Raby、Roy D. Schwarz、Carolyn J. Spencer、Anthony J. Thomas、Juan C. Jaen

  DOI：10.1021/jm960683m

  日期：1998.7.1

  The synthesis and SAR of a series of (Z)-(+/-)-1-azabicyclo[2.2. 1]heptan-3-one, O-(3-aryl-2-propynyl)oximes are described. The biochemistry and pharmacology of 24Z (PD 142505) and its enantiomers are highlighted. 24Z is functionally an m1-selective muscarinic agonist. Efficacy and m1 selectivity reside in the R enantiomer, (R)-24Z (CI-1017).

  一系列（Z）-（+/-）-1-氮杂双环[2.2。]的合成和SAR。1]庚烷-3-酮，O-（3-芳基-2-丙炔基）肟被描述。重点介绍了24Z（PD 142505）及其对映异构体的生物化学和药理作用。24Z在功能上是m1选择性毒蕈碱激动剂。功效和m1选择性存在于R对映异构体（R）-24Z（CI-1017）中。
• Synthesis and anti-HIV-1 activity of 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-one (TIBO) derivatives
  作者：Michael J. Kukla、Henry J. Breslin、Rudi Pauwels、Cynthia L. Fedde、Milton Miranda、Malcolm K. Scott、Ronald G. Sherrill、Alfons Raeymaekers、Jozef Van Gelder

  DOI：10.1021/jm00106a040

  日期：1991.2

  A series of 6-substituted 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-ones (9) have been synthesized and tested for their ability to inhibit the replication of the HIV-1 virus in MT-4 cells. Two synthetic methods are described, one of which allows the synthesis of single enantiomers of the final products. A structure-activity study was done within the series of compounds to determine the optimum group for the 6-position substitution and to determine whether the activity was enantiospecific at the 5-position, which was substituted with a methyl group. The best analogue, 9jj, inhibited HIV-1 with an IC50 of 4-mu-M, which is comparable to the activity level of DDI, a 2',3'-dideoxynucleoside-type structure undergoing clinical trials as an anti-AIDS therapy.
• Bohlmann; Viehe, Chemische Berichte, 1954, vol. 87, p. 712,721
  作者：Bohlmann、Viehe

  DOI：——

  日期：——
• Roberts, Charles; Walton, John C., Journal of the Chemical Society. Perkin transactions II, 1981, p. 553 - 560
  作者：Roberts, Charles、Walton, John C.

  DOI：——

  日期：——