(3E,5E)-5-methylhepta-3,5-dien-1-ol | 616873-93-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3E,5E)-5-methylhepta-3,5-dien-1-ol
• CAS: 616873-93-9
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: HFEMKCDBEJZPCG-APHNTDFBSA-N

物化性质

• 沸点：
  200.3±9.0 °C(Predicted)
• 密度：
  0.869±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (3E,5E)-5-methylhepta-3,5-dien-1-ol 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3E,5E)-5-methyl-hepta-3,5-dienal
  参考文献：
  名称：

  Tandem Wittig–intramolecular Diels–Alder cycloaddition of ester-tethered 1,3,9-decatrienes under microwave heating

  摘要：

  Intramolecular Diels Alder (IMDA) cycloaddition of the ester-tethered 1,3,9,-decatrienes possessing a carbonyl substituent at C10 has been investigated under controlled microwave heating (MeCN, 180 degrees C) to afford a variety of 3,4,4a,7,8,8a-hexahydroisochromen-1-ones in 53-89% yields and in 64:36-79:21 ratios for the cis and trans isomers. Under the same microwave heating conditions, a tandem Wittig-IMDA cycloaddition, starting from the alpha-bromoacetates of 3,5-hexadien-1-ols and glyoxalate/phenylglyoxal hydrates in the presence of PPh3 and 2,6-lutidine, has been demonstrated, furnishing 3,4,4a,7,8,8a-hexahydroisochromen-1-one adducts in 73-91% yields in favor of the cis isomers. During this tandem process, three consecutive carbon carbon bonds in the end products were efficiently formed with the aid of microwave irradiation within short reaction times. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.088
• 作为产物：
  描述：

  反式-2-甲基-2-丁烯醛 、 (3-羟丙基)三苯基溴化鏻 在 正丁基锂 作用下， 以84%的产率得到(3E,5E)-5-methylhepta-3,5-dien-1-ol
  参考文献：
  名称：

  Synthesis of an Isomer of theOxaspirobicyclic Tetronic Acid Unit of the CCK-B ReceptorAntagonist Tetronothiodin

  摘要：

  我们从二烯醇 4 中分五个步骤合成了一种 CCK-B 受体拮抗剂 tetronothiodin 的氧杂螺环双环四酸单元异构体，其螺环中心为非对映异构体。

  DOI：

  10.1055/s-2003-39287

文献信息

• Catalytic Asymmetric Vinylogous Prins Cyclization: A Highly Diastereo- and Enantioselective Entry to Tetrahydrofurans
  作者：Youwei Xie、Gui-Juan Cheng、Sunggi Lee、Philip S. J. Kaib、Walter Thiel、Benjamin List

  DOI：10.1021/jacs.6b09129

  日期：2016.11.9

  cyclization. This reaction constitutes an efficient approach for highly diastereo- and enantioselective synthesis of tetrahydrofurans (THFs) and is catalyzed by a confined chiral imidodiphosphoric acid (IDP). Aromatic and heteroaromatic aldehydes react with various 3,5-dien-1-ols to afford 2,3-disubstituted THFs in excellent selectivity (d.r. > 20:1, e.r. up to 99:1). Aliphatic aldehydes react with similarly

  我们描述了第一个催化不对称乙烯基 Prins 环化的设计和开发。该反应构成了四氢呋喃 (THF) 的高度非对映选择性和对映选择性合成的有效方法，并由受限的手性亚胺二磷酸 (IDP) 催化。芳香族和杂芳香族醛与各种 3,5-二烯-1-醇反应，以优异的选择性（dr > 20:1，er 高达 99:1）得到 2,3-二取代的 THF。当使用高酸性的亚氨基二磷亚胺酯 (IDPi) 催化剂时，脂肪醛的反应结果也同样出色。对于外消旋二烯醇，反应通过动力学拆分进行。DFT 计算提出了异常高立体选择性的解释。
• Acid-catalysed intramolecular addition of β-ketoesters to 1,3-dienes
  作者：Marie Vayer、Weizhen Fang、Régis Guillot、Sophie Bezzenine-Lafollée、Christophe Bour、Vincent Gandon

  DOI：10.1039/c6ob02122k

  日期：——

  1,3-Dienyl β-keto esters are cyclised into bicyclolactones using the Bi(OTf)3/TfOH catalytic system. This reaction represents a rare case of simultaneous C–C and C–O bond formation at positions 1 and 3 of a 1,3-diene. Application to the synthesis of ramulosin is presented.

  使用Bi（OTf）3 / TfOH催化系统将1,3-二烯基β-酮酸酯环化成双环内酯。该反应代表了在1,3-二烯的1和3位同时形成C–C和C–O键的罕见情况。介绍了在Ramulosin合成中的应用。
• Modular Design of Chiral Conjugate-Base-Stabilized Carboxylic Acids: Catalytic Enantioselective [4 + 2] Cycloadditions of Acetals
  作者：Zhengbo Zhu、Minami Odagi、Nantamon Supantanapong、Weici Xu、Jaan Saame、Helmi-Ulrika Kirm、Khalil A. Abboud、Ivo Leito、Daniel Seidel

  DOI：10.1021/jacs.0c07212

  日期：2020.9.9

  Readily available 1,2-amino alcohols provide the framework for a new generation of chiral carboxylic acid catalysts that rival the acidity of the widely used chiral phosphoric acid catalyst (S)-TRIP. Covalently linked thiourea sites stabilize the carboxylate conjugate bases of these catalysts via anion-binding, an interaction that is largely responsible for the low pKa values. The utility of the new

  易于获得的 1,2-氨基醇为新一代手性羧酸催化剂提供了框架，其酸度可与广泛使用的手性磷酸催化剂 (S)-TRIP 的酸度相媲美。共价连接的硫脲位点通过阴离子结合稳定这些催化剂的羧酸盐共轭碱，这种相互作用是造成低 pKa 值的主要原因。新催化剂的效用在水杨醛衍生的缩醛与高烯丙醇和双烯丙醇的具有挑战性的 [4+2] 环加成的背景下进行了说明，以高度对映选择性的方式提供多环色满。
• Tandem Wittig–intramolecular Diels–Alder cycloaddition of ester-tethered 1,3,9-decatrienes under microwave heating
  作者：Jinlong Wu、Xiuqing Jiang、Jingjing Xu、Wei-Min Dai

  DOI：10.1016/j.tet.2010.10.088

  日期：2011.1

  Intramolecular Diels Alder (IMDA) cycloaddition of the ester-tethered 1,3,9,-decatrienes possessing a carbonyl substituent at C10 has been investigated under controlled microwave heating (MeCN, 180 degrees C) to afford a variety of 3,4,4a,7,8,8a-hexahydroisochromen-1-ones in 53-89% yields and in 64:36-79:21 ratios for the cis and trans isomers. Under the same microwave heating conditions, a tandem Wittig-IMDA cycloaddition, starting from the alpha-bromoacetates of 3,5-hexadien-1-ols and glyoxalate/phenylglyoxal hydrates in the presence of PPh3 and 2,6-lutidine, has been demonstrated, furnishing 3,4,4a,7,8,8a-hexahydroisochromen-1-one adducts in 73-91% yields in favor of the cis isomers. During this tandem process, three consecutive carbon carbon bonds in the end products were efficiently formed with the aid of microwave irradiation within short reaction times. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of an Isomer of theOxaspirobicyclic Tetronic Acid Unit of the CCK-B ReceptorAntagonist Tetronothiodin
  作者：Philip C. Page、Hooshang Vahedi、Kevin J. Batchelor、Stephen J. Hindley、Mark Edgar、Paul Beswick

  DOI：10.1055/s-2003-39287

  日期：——

  An isomer of the oxaspirobicyclic tetronic acid unit of the CCK-B Receptor antagonist tetronothiodin, diastereoisomeric at the spiro centre, has been synthesized in five steps from dienol 4.

  我们从二烯醇 4 中分五个步骤合成了一种 CCK-B 受体拮抗剂 tetronothiodin 的氧杂螺环双环四酸单元异构体，其螺环中心为非对映异构体。