3,3-二甲基己-5-烯-1-醇 | 86549-24-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3,3-二甲基己-5-烯-1-醇
• 英文名称: 3,3-dimethylhex-5-en-1-ol
• CAS: 86549-24-8
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: IWTQWFNSSAKXCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  3,3-二甲基己-5-烯-1-醇 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 三光气 、 palladium on activated charcoal 、 氢气 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 8.08h， 生成 (2R,4S,7S)-7-tert-butyl-N-[(1R,2S)-2-cyclopropyl-1-(cyclopropylsulfonylcarbamoyl)cyclopropyl]-2,18-dimethoxy-13,13-dimethyl-6,9-dioxo-10-oxa-5,8-diazatetracyclo[15.5.3.12,5.020,24]hexacosa-1(23),17,19,21,24-pentaene-4-carboxamide
  参考文献：
  名称：

  The discovery and optimization of naphthalene-linked P2-P4 Macrocycles as inhibitors of HCV NS3 protease

  摘要：

  Naphthalene-linked P2-P4 macrocycles within a tri-peptide-based acyl sulfonamide chemotype have been synthesized and found to inhibit HCV NS3 proteases representing genotypes 1a and 1b with single digit nanomolar potency. The pharmacokinetic profile of compounds in this series was optimized through structural modifications along the macrocycle tether as well as the P1 subsite. Ultimately a compound with oral bioavailability of 100% in rat, and a long half-life in plasma was obtained. However, compounds in this macrocyclic series exhibited cardiac effects in an isolated rabbit heart model and for this reason further optimization efforts were discontinued. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.11.005
• 作为产物：
  描述：

  ethyl 3,3-dimethyl-5-hexenoate 在 lithium aluminium tetrahydride 作用下， 以88%的产率得到3,3-二甲基己-5-烯-1-醇
  参考文献：
  名称：

  Synthesis of trans-Fused Sesquiterpenoid Analogues by Zirconocene-Mediated Metallo-ene Reaction

  摘要：

  二丁基锆烯介导的甲氧基烯丙基反式选择性环化，然后与亲电物反应，是合成功能化环戊烷衍生物的便捷方法。环戊烷衍生物的闭环偏析反应为合成具有非天然反式-[3.4.0]双环壬烷骨架的倍半萜类似物提供了一个通用的构筑基块。

  DOI：

  10.1055/s-0029-1217738

文献信息

• Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers
  作者：Ilyas A. Berhane、Ameya S. Burde、Jonathan J. Kennedy-Ellis、Eva Zurek、Sherry R. Chemler

  DOI：10.1039/d1cc03515k

  日期：——

  The enantioselective copper-catalyzed oxidative coupling of alkenols with styrenes for the construction of dihydropyrans, isochromans, pyrans and morpholines is reported. A concise formal synthesis of a σ1 receptor ligand using this alkene carboetherification methodology was demonstrated. Ligand, solvent and base all impact reaction efficiency. DFT transition state calculations are presented.

  报道了烯醇与苯乙烯的对映选择性铜催化氧化偶联，用于构建二氢吡喃、异色满、吡喃和吗啉。证明了使用这种烯烃碳醚化方法的 σ 1受体配体的简明形式合成。配体、溶剂和碱都会影响反应效率。给出了 DFT 过渡态计算。
• Transannular cyclisation as a stratagem in synthesis. A total synthesis of (±)-pentalenene
  作者：Gerald Pattenden、Simon J. Teague

  DOI：10.1016/s0040-4020(01)87743-7

  日期：1987.1

  A total synthesis of the triquinane sesquiterpene (±)-pentalenene(1) found in Streptomyces, based on transannular cyclisation of the bicyclo [6.3.0] undecadiene (7) in the presence of boron trifluoride etherate is described. The bicyclo(6.3.0]undecadiene(7) was elaborated from the silyl enol ether(36) using a unique intramolecular [2+2] photocycloaddition - Grob fragmentation sequence leading to (8)

  基于在三氟化硼醚化物存在下双环[6.3.0]十一碳二烯（7）的环状环化，描述了在链霉菌中发现的三喹烷倍半萜烯（±）-戊烯（1）的总合成。使用独特的分子内[2 + 2]光环加成反应，从甲硅烷基烯醇醚（36）合成了双环（6.3.0）十一碳二烯（7）-Grob片段序列导致（8）[viz（36）→（37）和（38）→（8）]，然后在三水合三水合铑的存在下进行烯化为（40）和异构化。
• Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin
  作者：Rebecca E. Ruscoe、Neal J. Fazakerley、Huanming Huang、Sabine Flitsch、David J. Procter

  DOI：10.1002/chem.201504343

  日期：2016.1.4

  novel tricyclic architectures inspired by pleuromutilin. SmII‐mediated radical cyclization cascades of dialdehydes, prepared using a new, one‐pot, copper‐catalyzed double organomagnesium addition to β‐chlorocyclohexenone, proceed with complete sequence selectivity and typically with high diastereocontrol to give analogues of the target core. Our expedient approach (ca. 7 steps) allows non‐traditional,

  涉及简单制备的起始材料的通用合成序列提供了受截短侧耳素启发的多种新颖的三环结构的快速获得。 Sm II介导的二醛自由基环化级联是使用一种新的、一锅法、铜催化的双有机镁加成到 β-氯环己烯酮制备的，具有完全的序列选择性和通常具有高非对映控制，以产生目标核心的类似物。我们的权宜方法（大约 7 个步骤）允许通过非传统的从头合成方式获得无法通过半合成从天然产物中制备的重要抗菌剂的类似物。
• Hepatitis C Virus Inhibitors
  申请人：Hiebert Sheldon

  公开号：US20100080770A1

  公开（公告）日：2010-04-01

  Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

  揭示了具有一般式的丙型肝炎病毒抑制剂。还揭示了包含这些化合物的组合物以及使用这些化合物抑制HCV的方法。
• A Tandem Ester Cleavage-Michael Addition Reaction for the Synthesis of Oxygen Heterocycles
  作者：R. A. Bunce、M. J. Bennett

  DOI：10.1080/00397919308013298

  日期：1993.4

  Abstract A tandem ester cleavage-Michael addition sequence has been developed for the preparation of five- and six-ring oxygen heterocycles bearing an acetic acid residue at C-2. Treatment of ethyl 6- or 7-acetyloxy-2-alkenoates with ethanolic sodium ethoxide affords the tetrahydrofuran and tetrahydropyran products in 70–90% yields. The reaction is clean and appears to be a general route for the preparation

  摘要 已经开发了串联酯裂解-迈克尔加成序列，用于制备在 C-2 处带有乙酸残基的五环和六环氧杂环。用乙醇乙醇钠处理 6- 或 7-乙酰氧基-2- 烯酸乙酯，得到四氢呋喃和四氢吡喃产物，产率 70-90%。该反应是干净的，似乎是制备这些化合物的一般途径。初始乙酸酯裂解的空间位阻和闭合大环时不利的熵似乎是该过程的唯一限制。