6-甲基庚-1,5-二烯-4-醇 | 33698-82-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-甲基庚-1,5-二烯-4-醇
• 英文名称: 6-methyl-1,5-heptadien-4-ol
• 英文别名: 6-methylhepta-1,5-dien-4-ol；1,5-Heptadien-4-ol, 6-methyl-
• CAS: 33698-82-7
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: HQBPNXLPHSBKRK-UHFFFAOYSA-N

物化性质

• 沸点：
  70-71 °C(Press: 20 Torr)
• 密度：
  0.858±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：

  6-甲基庚-1,5-二烯-4-醇 在 chromium trioxide-pyridine complex 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 120.0h， 生成 5,5-Dimethyl-bicyclo<2.1.1>hexanon-(2)
  参考文献：
  名称：

  Regiochemical control in intramolecular photochemical reactions of 1,5-hexadien-3-ones and 1-acyl-1,5-hexadienes

  摘要：

  DOI：

  10.1021/ja00343a036
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 2-丙烯基锂 以 四氢呋喃 为溶剂， 反应 4.0h， 以78%的产率得到6-甲基庚-1,5-二烯-4-醇
  参考文献：
  名称：

  Regio- and Diastereoselective Ene Reaction of 4-Phenyl-1,2,4-triazoline-3,5-dione with Chiral Allylic Alcohols and Their Derivatives

  摘要：

  Chiral allylic alcohols la-e reacted with 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) in CH2Cl2 to produce 3-amino-1-alken-4-ols 2 and 3 in 78-89% yields, with 68-90% diastereomeric excess (de) in favor of the three isomer. Chiral allylic ethers If,g and acetates Ih,i gave similar yields but lower de (34-66%). Reaction of allylic alcohols 6a-e with PTAD in CH2Cl2 produced 1,3-regioisomers 7 and 8 exclusively in 33-65% yields without apparent diastereoselectivity, except when R-1 was a Bu-t group, in which case only syn product 7 was formed. However, when 6a or 6c was subjected to reaction with PTAD in a polar solvent, up to 88% de was observed. Reaction of allylic ethers 6f,g and acetates 6h,i with PTAD in CH2Cl2 also produced 7 and 8 exclusively with improved yields (56-96%) and diastereoselectivity (50-100% de in favor of the syn isomer).

  DOI：

  10.1021/jo980835g

文献信息

• Enantioselective C−C Bond Formation by Rhodium-Catalyzed Tandem Ylide Formation/[2,3]-Sigmatropic Rearrangement between Donor/Acceptor Carbenoids and Allylic Alcohols
  作者：Zhanjie Li、Huw M. L. Davies

  DOI：10.1021/ja9075293

  日期：2010.1.13

  The rhodium-catalyzed reaction of racemic allyl alcohols with methyl phenyldiazoacetate or methyl styryldiazoacetate results in a two-step process, an initial oxonium ylide formation followed by a [2,3]-sigmatropic rearrangement. This process competes favorably with the more conventional O-H insertion chemistry as long as donor/acceptor carbenoids and highly substituted allyl alcohols are used as substrates

  外消旋烯丙醇与苯基重氮乙酸甲酯或苯乙烯基重氮乙酸甲酯的铑催化反应产生一个两步过程，首先形成氧鎓叶立德，然后进行 [2,3]-σ 重排。只要使用供体/受体类卡宾和高度取代的烯丙醇作为底物，该过程就可以与更传统的 OH 插入化学竞争。当反应由 Rh(2)(S-DOSP)(4) 催化时，会以高对映选择性 (85-98% ee) 产生具有两个相邻季中心的叔 α-羟基羧酸衍生物。
• Singlet oxygen addition to chiral allylic alcohols and subsequent peroxyacetalization with β-naphthaldehyde: synthesis of diastereomerically pure 3-β-naphthyl-substituted 1,2,4-trioxanes
  作者：Axel G. Griesbeck、Tamer T. El-Idreesy、Johann Lex

  DOI：10.1016/j.tet.2006.05.093

  日期：2006.11

  The synthesis of a series of eight β-naphthyl-substituted 1,2,4-trioxanes 3a–h by a sequence of singlet oxygen ene reaction of allylic alcohols 1a–h and Lewis acid catalyzed peroxyacetalization of the allylic hydroperoxides 2a–h with β-naphthaldehyde is reported. The ene reactions were performed by solid-state photooxygenation in dye-crosslinked polystyrene beads and resulted in mixtures of diastereoisomeric

  一系列八个β萘基取代的1,2,4-三恶烷的合成图3a - ħ通过烯丙基醇的单重态氧烯反应的序列1A - ħ和烯丙基氢过氧化物的路易斯酸催化peroxyacetalization 2A - ħ与β报道了萘醛。烯类反应是通过在染料交联的聚苯乙烯珠粒中进行固态光氧合而进行的，并生成非对映异构氢过氧化物2的混合物。三氟化硼催化peroxyacetalization导致形成3，以及1,2,4-三氧杂环己烷4和5通过酸催化的β-氢过氧醇裂解形成。
• 1,2,5,10,11,14-Hexaoxadispiro[5.2.5.2]hexadecanes: Novel Spirofused Bis-Trioxane Peroxides
  作者：Axel Griesbeck、Lars-Oliver Höinck、Johann Lex、Jörg Neudörfl、Dirk Blunk、Tamer El-Idreesy

  DOI：10.3390/molecules13081743

  日期：——

  cyclohexane-1,4-dione with allylic hydroperoxides 2a-d, bearing an additional hydroxy group in the homoallylic position, by diastereoselective photooxygenation of allylic alcohols 1a-d and subsequent BF3-catalyzed peroxyacetalization with the diketone. From the reaction of a monoprotected cyclohexane-1,4-dione 5 with the allylic hydroperoxide 6 derived from the singlet oxygenation of methyl hydroxytiglate

  通过非对映选择性光氧化，环己烷-1,4-二酮与烯丙基氢过氧化物 2a-d 反应获得一组新的双螺稠 1,2,4-三恶烷 4a-d，在同烯丙基位置带有一个额外的羟基烯丙醇 1a-d 和随后的 BF3 催化过氧化缩醛与二酮。从单保护的环己烷-1,4-二酮 5 与衍生自羟甲酸甲酯单线态氧化的烯丙基氢过氧化物 6 的反应中，获得一种单螺环化合物、1,2,4-三恶烷酮 7 以及混合物8. 双 1,2,4-三恶烷的非对映异构体的结构通过 DFT 方法进行了理论上的检查，并与 X 射线结构数据进行了比较，以评估其优先性三恶烷环构象取向。
• Preparation and Reactions of Masked Allylic Organozinc Reagents
  作者：Philip Jones、Paul Knochel

  DOI：10.1021/jo981623m

  日期：1999.1.1

  Allylic zinc reagents have been prepared from sterically hindered homoallylic alcohols 10 and 13, using a novel fragmentation reaction of the corresponding zinc alkoxide, without any homocoupling products. These allylic zinc reagents react with a range of electrophiles in good to excellent yields. Substituted allylic zinc reagents have also been prepared in this manner. alpha-Substituted homoallylic

  烯丙基锌试剂已经由空间受阻的均烯丙基醇10和13使用相应的烷氧基锌的新型裂解反应制备，没有任何均偶联产物。这些烯丙基锌试剂可与一系列亲电试剂反应，收率好至极好。也已经以此方式制备了取代的烯丙基锌试剂。α-取代的均烯丙基醇37、46和51在断裂-烯丙基化序列之后仅给出α-取代的产物；这些产品不仅可以区域选择性地获得，而且还具有极高的抗非对映选择性。同样，γ-取代的均烯丙基醇57和58进行片段化-烯丙基化反应，得到γ-取代的产物。还已经证明该反应在锌盐中是催化的。
• Masked allylic zinc reagents
  作者：Philip Jones、Nicolas Millot、Paul Knochel

  DOI：10.1039/a805952g

  日期：——

  The preparation of allylic zinc reagents using the fragmentation of sterically hindered tertiary homoallylic alcohols is described

  介绍了利用立体受阻叔均烯丙基醇的碎片制备烯丙基锌试剂的方法