4-(1-hydroxybut-3-en-1-yl)benzaldehyde | 207994-96-5

• 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: 4-(1-hydroxybut-3-en-1-yl)benzaldehyde
• 英文别名: 4-(1-hydroxy-3-butenyl)benzaldehyde；4-(1-Hydroxy-3-buten-1-yl)benzaldehyde；4-(1-hydroxybut-3-enyl)benzaldehyde
• CAS: 207994-96-5
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: RUWVFVYFSCPDBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(1-hydroxybut-3-en-1-yl)benzaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以61%的产率得到1-(4-羟甲基苯基)-3-丁烯-1-醇
  参考文献：
  名称：

  Ruthenium-catalyzed isomerization of homoallylic alcohols in water

  摘要：

  Through the catalysts of RuCl2(PPh3)(3), the functional groups of homoallylic alcohols are repositioned to give allylic alcohols with controlled regioselectivity. The reaction proceeds most efficiently in an aqueous media. The selectivity in product formation is affected by the reaction temperature and the amount of the catalyst being used. A higher reaction temperature and the use of a smaller amount of the catalyst are preferable for the formation of allylic alcohols. The reaction process was postulated as a tandem olefin migration-allylic rearrangement. Under the same reaction conditions, the functional groups of allylic alcohols undergo allylic rearrangements. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00252-x
• 作为产物：
  描述：

  乙酸烯丙酯 、 对苯二甲醛 在 [Rh(TMEDA)(CO2)][Rh(Cl)2(CO)2] 、 一氧化碳 、 cesium carbonate hydrate 作用下， 以 四氢呋喃 为溶剂， 100.0 ℃ 、1.0 MPa 条件下， 反应 24.0h， 以78%的产率得到4-(1-hydroxybut-3-en-1-yl)benzaldehyde
  参考文献：
  名称：

  Rhodium-Catalyzed Reductive Allylation of Conjugated Aldehydes with Allyl Acetate

  摘要：

  Reductive allylation of aryl and alkenyl aldehydes with allyl acetate catalyzed by the ionic diamine carbonyl rhodium complex, [Rh(TMEDA)(CO)(2)][RhCl(2)(CO)(2)], under a carbon monoxide atmosphere afforded the corresponding homoallylic alcohols in good isolated yields.

  DOI：

  10.1021/jo902706p

文献信息

• Indium-Employed One-Pot Sequential Double Nucleophilic Attack on a Symmetrical Dicarboxaldehyde
  作者：Akio Baba、Srinivasarao Arulananda Babu、Makoto Yasuda、Ikuya Shibata

  DOI：10.1055/s-2004-822931

  日期：——

  A novel concept of one-pot sequential double nucleophilic attacks using two different nucleophiles to a molecule having identical functionalities was established via an indium-employed allylation strategy involving an HOAc quenching after the first allylation.

  使用两种不同的亲核试剂对具有相同功能的分子进行一锅连续双亲核攻击的新概念是通过使用铟的烯丙基化策略建立的，该策略涉及在第一次烯丙基化后的 HOAc 淬灭。
• Zinc/Bismuth-Mediated Allylation Reaction of Biomass Feedstocks: Synthesis of Furanic Diols
  作者：Mukund P. Sibi、Soumen Biswas、Prakash Kannaboina

  DOI：10.1055/a-2241-6966

  日期：——

  Biomass-based diols have been synthesized by a Zn/Bi-mediated Barbier-type of reaction from furanic aldehydes and allyl halides to access allylated diols. The allylated diols can be readily converted into alkylated diols by hydrogenation. These furanic diols could be potential replacements for fossil fuel based bisphenol A (BPA) which has an adverse endocrine-disrupting effect on humans. This mild

  通过锌/铋介导的巴比尔型反应，从呋喃醛和烯丙基卤化物合成基于生物质的二醇，以获得烯丙基化的二醇。烯丙基化的二醇可以通过氢化容易地转化为烷基化的二醇。这些呋喃二醇可能是基于化石燃料的双酚 A (BPA) 的潜在替代品，双酚 A 对人类具有不利的内分泌干扰作用。这种温和且绿色的方案可提供高产率的对称和非对称二醇。烯丙基双键的化学选择性还原为二醇提供了独特的取代。
• JPH03112940A
  申请人：——

  公开号：JPH03112940A

  公开（公告）日：1991-05-14
• Ruthenium-catalyzed isomerization of homoallylic alcohols in water
  作者：Dong Wang、Dongli Chen、John X. Haberman、Chao-Jun Li

  DOI：10.1016/s0040-4020(98)00252-x

  日期：1998.5

  Through the catalysts of RuCl2(PPh3)(3), the functional groups of homoallylic alcohols are repositioned to give allylic alcohols with controlled regioselectivity. The reaction proceeds most efficiently in an aqueous media. The selectivity in product formation is affected by the reaction temperature and the amount of the catalyst being used. A higher reaction temperature and the use of a smaller amount of the catalyst are preferable for the formation of allylic alcohols. The reaction process was postulated as a tandem olefin migration-allylic rearrangement. Under the same reaction conditions, the functional groups of allylic alcohols undergo allylic rearrangements. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Rhodium-Catalyzed Reductive Allylation of Conjugated Aldehydes with Allyl Acetate
  作者：Maksym Vasylyev、Howard Alper

  DOI：10.1021/jo902706p

  日期：2010.4.16

  Reductive allylation of aryl and alkenyl aldehydes with allyl acetate catalyzed by the ionic diamine carbonyl rhodium complex, [Rh(TMEDA)(CO)(2)][RhCl(2)(CO)(2)], under a carbon monoxide atmosphere afforded the corresponding homoallylic alcohols in good isolated yields.