1-phenyl-2-vinyl-3-buten-1-ol | 10544-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenyl-2-vinyl-3-buten-1-ol
• 英文别名: 1-phenyl-2-vinyl-3-buten-l-ol；1-phenyl-2-vinylbut-3-en-1-ol；4-phenyl-3-vinylbut-1-en-4-ol；2-Ethenyl-1-phenylbut-3-en-1-ol
• CAS: 10544-99-7；197020-85-2；197020-90-9
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: XHRXQFGXDYZLHL-UHFFFAOYSA-N

物化性质

• 沸点：
  122-123 °C(Press: 12 Torr)
• 密度：
  0.988 g/cm3(Temp: 21 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-vinyl-3-buten-1-ol 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.75h， 生成 (3aS,4R,7aR)-5-ethenyl-2-ethyl-4-phenyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione
  参考文献：
  名称：

  Skeletal Diversity via a Branched Pathway:  Efficient Synthesis of 29 400 Discrete, Polycyclic Compounds and Their Arraying into Stock Solutions

  摘要：

  We report the synthesis and arraying of 29 400 structurally diverse and complex polycyclic carbocycles using diversity-oriented synthesis (DOS) and the "one bead-one stock solution" technology platform. Skeletal diversity, a difficult challenge in DOS, was achieved with a branching reaction pathway using one or two Diels-Alder reactions. This pathway yields small molecules having 10 different skeletons.

  DOI：

  10.1021/ja028086e
• 作为产物：
  描述：

  1,4-戊二烯 、 苯甲醛 生成 1-phenyl-2-vinyl-3-buten-1-ol
  参考文献：
  名称：

  Hutchings, Michael G.; Paget, Walter E.; Smith, Keith, Journal of Chemical Research, Miniprint, 1983, # 2, p. 342 - 351

  摘要：

  DOI：

文献信息

• Asymmetric Addition of Allylic Stannanes to Aldehydes Catalyzed by BINAP•Ag(I) Complex
  作者：Akira Yanagisawa、Hiroshi Nakashima、Yoshinari Nakatsuka、Atsushi Ishiba、Hisashi Yamamoto

  DOI：10.1246/bcsj.74.1129

  日期：2001.6

  Catalytic asymmetric allylation of aldehydes with allylic trialkylstannanes was achieved with BINAP•AgOTf complex as catalyst. The chiral silver(I) catalyst was readily prepared by stirring an equimolar mixture of BINAP and silver(I) triflate in THF at room temperature. The allylation of a variety of aromatic and α,β-unsaturated aldehydes resulted in high yields and remarkable enantioselectivities

  以BINAP•AgOTf配合物为催化剂实现了醛与烯丙基三烷基锡烷的催化不对称烯丙基化反应。通过在室温下在 THF 中搅拌 BINAP 和三氟甲磺酸银 (I) 的等摩尔混合物，很容易制备手性银 (I) 催化剂。各种芳香醛和 α,β-不饱和醛的烯丙基化产生了高产率和显着的对映选择性。γ-取代的烯丙基锡烷如2-丁烯基三丁基锡烷和三烷基-2,4-戊二烯基锡烷的加成专门得到γ-加合物。无论双键的构型如何，在与 2-丁烯基三丁基锡烷的反应中也获得了高抗选择性。
• Tetracycline analogues with a selective inhibitory effect on HIF-1α
  作者：Y. Bendiabdellah、K. M. Rahman、B. Uranchimeg、K. S. Nahar、D. Antonow、R. H. Shoemaker、G. Melillo、G. Zinzalla、D. E. Thurston

  DOI：10.1039/c4md00111g

  日期：——

  As part of a programme to discover novel transcription factor inhibitors, a 40-membered library of tetracycline analogues was screened to identify potential HIF-1 inhibitors. Two novel analogues (5b and 5c) with significant HIF-1 modulation properties were identified. These molecules possess good cellular penetration properties, and provide significant down-regulation of VEGF in U251 cells.

  作为发现新型转录因子抑制剂计划的一部分，筛选了一个包含40个四环素类似物的库，以鉴定潜在的HIF-1抑制剂。发现了两种具有显著HIF-1调节特性的新型类似物（5b和5c）。这些分子具有良好的细胞渗透特性，并在U251细胞中显著下调VEGF的表达。
• Petasis Borono-Mannich Reaction and Allylation of Carbonyl Compounds via Transient Allyl Boronates Generated by Palladium-Catalyzed Substitution of Allyl Alcohols. An Efficient One-Pot Route to Stereodefined α-Amino Acids and Homoallyl Alcohols
  作者：Nicklas Selander、Andreas Kipke、Sara Sebelius、Kálmán J. Szabó

  DOI：10.1021/ja074917a

  日期：2007.11.1

  was designed by integration of the pincer-complex-catalyzed borylation of allyl alcohols in the Petasis borono-Mannich reaction and in allylation of aldehydes and ketones. These procedures are suitable for one-pot synthesis of alpha-amino acids and homoallyl alcohols from easily available allyl alcohol, amine, aldehyde, or ketone substrates. In the presented transformations, the active allylating agents

  通过在 Petasis borono-Mannich 反应和醛和酮的烯丙基化中整合烯丙醇的钳形复合物催化硼化反应，设计了一种高效的一锅法。这些程序适用于从容易获得的烯丙醇、胺、醛或酮底物一锅法合成 α-氨基酸和高烯丙醇。在所提出的转化中，活性烯丙基化剂是原位生成的烯丙基硼酸衍生物。这些瞬态中间体被证明是对酸、碱、醇、水和空气稳定的物质，它们与各种醛/酮和亚胺亲电子试剂的烯丙基化反应条件具有高度的相容性。反应的硼酸盐来源是二硼酸或原位水解的二硼酸酯，以确保反应的废产物是无毒的硼酸。该反应的区域选择性和立体选择性非常好，因为几乎所有产物都以单一区域和立体异构体形式形成。所描述的程序适用于在支链烯丙基产物中产生季碳中心，而不会形成相应的线性烯丙基异构体。此外，包含三个立体中心的产品作为单一产品形成而没有形成其他非对映异构体。由于高度规范的连续过程，最多可以作为一锅序列选择性地执行四步、四组分转换
• High γ-selectivity in the coupling of penta-2,4-dienyl- and pent-2-en-4-ynylindium reagents with aldehydes
  作者：Tsunehisa Hirashita、Shin'ichirou Inoue、Hatsuo Yamamura、Masao Kawai、Shuki Araki

  DOI：10.1016/s0022-328x(97)00513-5

  日期：1997.12

  A variety of penta-2,4-dienyl- and pent-2-en-4-ynylindium reagents have been prepared in situ from the reaction of the corresponding allylic bromides with indium metal, and their reactions with carbonyl compounds have been examined. The reaction with aldehydes gives the corresponding homoallyl alcohols in high yields. The coupling occurs regioselectively at the γ-position of these indium reagents. No

  从相应的烯丙基溴化物与铟金属的反应中原位制备了各种五-2,4-二烯基-和戊-2-烯-4-吡啶鎓试剂，并研究了它们与羰基化合物的反应。与醛的反应以高收率得到相应的均烯丙基醇。偶联选择性地在这些铟试剂的γ-位发生。没有形成α-和ϵ-耦合产物。
• A consecutive Diels–Alder approach toward a Tet repressor directed combinatorial library
  作者：Christian Kormann、Frank W. Heinemann、Peter Gmeiner

  DOI：10.1016/j.tet.2006.04.092

  日期：2006.7

  generated by solution phase parallel synthesis applying a consecutive Diels–Alder strategy. Chemical methodology suitable for three-dimensional solution phase parallel synthesis was developed that enabled us to generate a collection of potential TetR inducers. The synthesis was built on cross-conjugated trienes as central building blocks facilitating two consecutive cycloaddition processes with different

  通过使用连续的Diels-Alder策略进行溶液相平行合成，生成了180个四环素类似物的组合库。开发了适用于三维溶液相平行合成的化学方法，使我们能够生成潜在的TetR诱导剂的集合。合成建立在交叉共轭三烯上，作为中心结构单元，可促进两个连续的具有不同的亲二烯体的环加成过程。在顺序暴露于萘醌和马来酰亚胺衍生物后，可以设想生成结合了多样性元素R 1 -R 5的2型碳环骨架。