[(1E,3E)-5-hydroxypenta-1,3-dien-1-yl]boronic acid | 163395-62-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: [(1E,3E)-5-hydroxypenta-1,3-dien-1-yl]boronic acid
• 英文别名: [(E,E)-5-hydroxypenta-1,3-dien-1-yl]boronic acid；((E,E)-5-hydroxypenta-1,3-dien-1-yl)boric acid；((1E,3E)-5-Hydroxypenta-1,3-dien-1-yl)boronic acid；[(1E,3E)-5-hydroxypenta-1,3-dienyl]boronic acid
• CAS: 163395-62-8
• 化学式: C₅H₉BO₃
• 分子量: 127.936
• InChiKey: HAVSNWCBVSMNTG-ZPUQHVIOSA-N

物化性质

• 沸点：
  334.0±44.0 °C(predicted)
• 密度：
  1.134±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(1E,3E)-5-hydroxypenta-1,3-dien-1-yl]boronic acid 在 sodium hydroxide 、 碘 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以62%的产率得到(2E,4E)-5-iodo-penta-2,4-dien-1-ol
  参考文献：
  名称：

  The suzuki reaction in stereocontrolled polyene synthesis: Retinol (vitamin A), its 9- and/or 13-demethyl analogs, and related 9-demethyl-dihydroretinoids

  摘要：

  A new synthesis of retinol (vitamin A) and 9- and/or 13-demethylretinols, with essentially complete control of regio- and stereochemistry, is described which is based on the thallium-accelerated, palladium-catalyzed cross-coupling reactions of (E)-1-alkenylboronic acids and (E)-1-alkenyl iodides (Suzuki reaction). The procedure has also been extended to the stereocontrolled synthesis of a series of 9-demethyl-dihydroretinoids of potential biological interest.

  DOI：

  10.1016/0040-4020(94)01108-c
• 作为产物：
  描述：

  (E)-2-penten-4-yn-1-ol 在 儿萘酚硼烷 、 水 作用下， 反应 18.0h， 生成 [(1E,3E)-5-hydroxypenta-1,3-dien-1-yl]boronic acid
  参考文献：
  名称：

  Mauleon, Pablo; Zeldin, Rachel M.; Gonzalez, Ana Z., Journal of the American Chemical Society, 2009, vol. 131, p. 6348 - 6349

  摘要：

  DOI：

文献信息

• Fast Synthesis of Complex Enantiopure Heterocyclic Scaffolds by a Tandem Sequence of Simple Transformations on α-Hydroxyaldehydes
  作者：Alexandre Cannillo、Stéphanie Norsikian、Pascal Retailleau、Marie-Elise Tran Huu Dau、Bogdan I. Iorga、Jean-Marie Beau

  DOI：10.1002/chem.201301712

  日期：2013.7.8

  Two tandems are faster than one! Properly sequenced reactions initiated by the Petasis aminoalcohol synthesis from boronic acids, diallylamine, and α‐hydroxyaldehydes, including free aldoses, leads to rapid construction of complex enantiopure structures (see scheme).

  两个坦丹比一个快！由Petasis氨基醇从硼酸，二烯丙基胺和α-羟醛（包括游离醛糖）合成引发的正确测序反应会导致快速构建复杂的对映纯结构（请参见方案）。
• Total synthesis, stereochemical assignment, and biological evaluation of L-755,807
  作者：Kosaku Tanaka、Yusuke Honma、Chihiro Yamaguchi、Lina Aoki、Minami Saito、Momoko Suzuki、Kazuhiro Arahata、Kaoru Kinoshita、Kiyotaka Koyama、Kenichi Kobayashi、Hiroshi Kogen

  DOI：10.1016/j.tet.2019.01.020

  日期：2019.2

  807 were established through total synthesis. All four possible stereoisomers were prepared via a convergent synthetic strategy, including a novel diastereoselective Darzens reaction of an α-alkoxy aldehyde with di-tert-butyl bromomalonate, an E-selective Horner–Wadsworth–Emmons reaction, and late-stage coupling of the ring and side-chain segments. Additionally, biological evaluation of the synthesized

  L-755,807的相对和绝对构型是通过全合成建立的。所有四种可能的立体异构体均是通过聚合合成策略制备的，包括α-烷氧基醛与溴化丙二酸二叔丁酯的新型非对映选择性Darzens反应，E-选择性霍纳-沃兹沃思-埃蒙斯反应，以及酯的后期偶联。环和侧链段。此外，对合成化合物的生物学评估表明，它们 对淀粉样β聚集体具有有效的抑制活性（IC 50 = 5–21μM），可用于治疗阿尔茨海默氏病。
• Total Synthesis of (−)-L-755,807: Establishment of Relative and Absolute Configurations
  作者：Kosaku Tanaka、Kenichi Kobayashi、Hiroshi Kogen

  DOI：10.1021/acs.orglett.6b00758

  日期：2016.4.15

  The first total synthesis of (−)-L-755,807 and its three stereoisomers was achieved by our Horner–Wadsworth–Emmons reaction for stereoselective formation of trisubstituted olefins, highly diastereoselective Darzens condensation to construct the epoxy-γ-lactam ring, and late-stage coupling of the ring and side-chain segments for efficient convergent synthesis. This synthesis shows that the originally

  （-）-L-755,807及其三个立体异构体的第一个全合成反应是通过我们的Horner-Wadsworth-Emmons反应进行的，该反应用于立体选择性地形成三取代的烯烃，高度非对映选择性的Darzens缩合反应以构建环氧-γ-内酰胺环，以及后期环和侧链链段的阶段偶联，以实现有效的收敛合成。该合成表明，天然（-）-L-755,807最初提出的结构是错误的，并确定了其相对和绝对构型。
• Use of Thallium(I) Ethoxide in Suzuki Cross Coupling Reactions
  作者：Scott A. Frank、Hou Chen、Roxanne K. Kunz、Matthew J. Schnaderbeck、William R. Roush

  DOI：10.1021/ol0062446

  日期：2000.8.1

  [reaction: see text]Thallium(I) ethoxide promotes Suzuki cross couplings for a range of vinyl- and arylboronic acids with vinyl and aryl halide partners in good to excellent yields. This reagent offers distinct advantages over thallium(I) hydroxide in terms of commercial availability, stability, and ease of use.

  [反应：请参阅文本]乙醇hall可促进一系列乙烯基和芳基硼酸与乙烯基和芳基卤化物伙伴的Suzuki交叉偶联，收率高至优异。就商业可获得性，稳定性和易用性而言，该试剂与氢氧化al（I）相比具有明显的优势。
• Stereoselective synthesis of polyenic alarm pheromones of cephalaspidean molluscs
  作者：Rosana Alvarez、María Herrero、Susana López、Angel R. de Lera

  DOI：10.1016/s0040-4020(98)00363-9

  日期：1998.6

  The stereospecific thallium-accelerated palladium-catalyzed cross-coupling of I-alkenyl boronic acids and I-alkenyl iodides (the Suzuki reaction) is the key step in an efficient approach to several polyenic pheromones isolated from cephalaspidean opisthobranch molluscs. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.