(Z)-4-chloro-but-2-en-1-ol | 1576-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-4-chloro-but-2-en-1-ol
• 英文别名: (Z)-4-chloro-2-buten-1-ol；(2Z)-4-chlorobut-2-en-1-ol；(Z)-4-chlorobut-2-en-1-ol
• CAS: 1576-93-8
• 化学式: C₄H₇ClO
• 分子量: 106.552
• InChiKey: WVRLAHTVGOLBEB-UPHRSURJSA-N

物化性质

• 沸点：
  83-89 °C(Press: 14 Torr)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2905590090

反应信息

• 作为反应物：
  描述：

  (Z)-4-chloro-but-2-en-1-ol 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以25%的产率得到(Z)-4-iodobut-2-en-1-ol
  参考文献：
  名称：

  Total Synthesis of Photoactivatable or Fluorescent Anandamide Probes: Novel Bioactive Compounds with Angiogenic Activity

  摘要：

  Endocannabinoids are endogenous polyunsaturated fatty acids involved in a multitude of health and disease processes. Recently, several lines of evidence suggest the presence of a novel non-CB1/CB2 anandamide receptor in endothelial cells. Thus, we synthesized two types of photoaffinity probes that contain either an arylazide group or a diazirin moiety, together with a fluorescent analogue. The key steps rely on selective hydrogenation of skipped tetrayne backbones and on copper-mediated cross-coupling reactions between diynic precursors. Three synthetic routes were investigated. In biological functional assays, we found that both the arylazide and the fluorescent probes induced robust increases in matrix metalloprotease activity and produced positive angiogenic responses in in vitro endothelial cell tube formation assays. Irradiation of the arylazide probe nicely enhanced this effect in both HUVEC and CBI-KO HUVEC. These results suggest that the arylazide and the fluorescent probes can be used to identify "non-C131/CB2 anandamide receptor" from endothelial cells.

  DOI：

  10.1021/jm8011382
• 作为产物：
  描述：

  顺式-1,2-二羟甲基乙烯 在 吡啶 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 以85%的产率得到(Z)-4-chloro-but-2-en-1-ol
  参考文献：
  名称：

  Synthesis of 2,5-Substituted Tetrahydrofurans by Pd(II)-Catalyzed Cyclization

  摘要：

  在钯(II)催化下，羟基取代的烯丙基醇环化反应定量生成了 2,5 取代的四氢呋喃顺式/反式混合物。

  DOI：

  10.2174/157017812802850258

文献信息

• A Mild and Convenient Barbier-Type Allylation of Aldehydes to Homoallylic Alcohols via Iodide Ion Promoted Stannylation of Allylic Bromides and Chlorides with Tin(II) Chloride
  作者：Toshiro Imai、Shinya Nishida

  DOI：10.1055/s-1993-25871

  日期：——

  Barbier-type allylation of aldehydes with allylic bromides and tin(II) chloride dihydrate is largely accelerated by adding stoichiometric or substoichiometric amounts of sodium iodide. This method has some merits such as lower temperature, shorter reaction time and/or more choices of solvents for the reaction. Moreover, the activation by the iodide ion enables the use of relatively unreactive allylic chlorides of various structural types (e.g., 3-chloro-2-chloromethylpropene as an isobutene dianion equivalent) and, thus, expands synthetic applicability of this reaction. The major role of the iodide salt is attributed to the in situ generation of the corresponding allylic iodide.

  巴比尔型醛与烯丙基溴和二水合氯化亚锡的偶联反应通过添加化学计量或亚化学计量的碘化钠，得到了显著的加速。这种方法具有一些优点，如较低的反应温度、更短的反应时间以及/或更多选择性的溶剂使用。此外，碘离子引发的活化使得可以利用相对不活泼的各种结构类型的烯丙基氯化物（例如，作为异丁烯二负离子等价物的3-氯-2-氯甲基丙烯），从而扩大了这一反应的合成应用范围。碘盐的主要作用归因于其在位生成相应的烯丙基碘化物。
• Some phenyl migrations in organophosphorus compounds
  作者：J. J. Brophy、K. L. Freeman、M. J. Gallagher

  DOI：10.1039/j39680002760

  日期：——

  triphenyl-2-phenylvinylphosphonium bromide, methyldiphenyl-2-phenylvinylphosphonium bromide, and halomethyltriphenylphosphonium halides are accompanied by phenyl migration from phosphorus to adjacent carbon. It is suggested that this migration is explained by the presence on the α-carbon atom of an electron-delocalizing substituent or a good leaving group.

  Buta-1,3-dien-1-基三苯基tri溴化物，三苯基-2-苯基乙烯基bro溴化物，甲基二苯基-2-苯基乙烯基yl溴化物和卤代甲基三苯基phosph卤化物的碱水解伴随有苯基从磷向相邻碳的迁移。建议通过电子离域取代基或良好的离去基团在α-碳原子上的存在来解释这种迁移。
• Ligand-Controlled Regiodivergence in the Copper-Catalyzed [2,3]- and [1,2]-Rearrangements of Iodonium Ylides
  作者：Bin Xu、Uttam K. Tambar

  DOI：10.1021/jacs.6b08624

  日期：2016.9.21

  allylic ylide rearrangements for the synthesis of complex molecules, the catalyst control of [2,3]- and [1,2]-rearrangements remains an unsolved problem. We developed the first regiodivergent [2,3]- and [1,2]-rearrangements of iodonium ylides that are controlled by copper catalysts bearing different ligands. In the presence of a 2,2'-dipyridyl ligand, diazoesters and allylic iodides react via a [2,3]-rearrangement

  尽管烯丙基叶立德重排对于复杂分子的合成很重要，[2,3]-和[1,2]-重排的催化剂控制仍然是一个未解决的问题。我们开发了第一个由带有不同配体的铜催化剂控制的碘鎓叶立德的区域发散[2,3]-和[1,2]-重排。在 2,2'-联吡啶配体存在下，重氮酯和烯丙基碘通过 [2,3]-重排途径发生反应。或者，膦配体有利于形成[1,2]-重排产物。以高产率、区域选择性和非对映选择性获得了一系列含有广泛官能团的 α-碘酯。氘标记研究表明区域选择性重排的不同机制。
• A Facile Synthesis of the Sex Pheromone of the Cabbage Looper Trichoplusia ni
  作者：Thanh-Danh Nguyen、Cong-Hao Nguyen、Chan Im、Chi-Hien Dang

  DOI：10.1007/s10600-016-1800-7

  日期：2016.9

  The sex pheromone of the cabbage looper Trichoplusia ni Hubner, (Z)-7-dodecen-1-yl acetate, was synthesized via a bimolecular nucleophilic substitution reaction between the Grignard reagent of the protected bromohydrin with (Z)-2-hepten-1-yl acetate in the presence of CuI catalyst as a key step. An efficient synthetic method of preparation of the pheromone was achieved from (Z)-2-butene-1,4-diol in

  通过保护溴醇的格氏试剂与 (Z)-2-hepten-1 之间的双分子亲核取代反应合成了卷心菜短纹夜蛾 Trichoplusia ni Hubner 的性信息素 (Z)-7-dodecen-1-yl acetate作为关键步骤，在 CuI 催化剂存在下乙酸酯。(Z)-2-丁烯-1,4-二醇分四步制备信息素的有效合成方法，总产率为22.1%。
• 4-Cyano-2-butenyl group: A new type of protecting group in oligonucleotide synthesis via phosphoramidite approach
  作者：Vasulinga T. Ravikumar、Zacharia S. Cheruvallath、Douglas L. Cole

  DOI：10.1016/s0040-4039(96)01496-7

  日期：1996.9

  4-Cyano-2-butenyl (CB) is a new type of protecting group for the internucleotidic bonds in the synthesis of oligodeoxyribonucleotides by the phosphoramidite approach. This group is stable to acidic conditions and can be removed under mild conditions by a δ-elimination pathway using aqueous ammonium hydroxide.

  4-氰基-2-丁烯基（CB）是通过亚磷酰胺方法合成寡脱氧核糖核苷酸中核苷酸间键的新型保护基。该基团对酸性条件稳定，在温和条件下可通过使用氢氧化铵水溶液的δ消除途径除去。