6-methyl-1,6-heptadien-3-ol | 79972-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-methyl-1,6-heptadien-3-ol
• 英文别名: 6-Methylhepta-1,6-dien-3-ol
• CAS: 79972-54-6
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: INSRWNOFDDRAKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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-methyl-1,6-heptadien-3-ol 以78%的产率得到
  参考文献：
  名称：

  SALOMON, R. G.;COUGHLIN, D. J.;GHOSH, S.;ZAGORSKI, M. G., J. AMER. CHEM. SOC., 1982, 104, N 4, 998-1007

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基-4-戊烯醛 、 乙烯基溴化镁 以 四氢呋喃 为溶剂， 以88%的产率得到6-methyl-1,6-heptadien-3-ol
  参考文献：
  名称：

  Copper(I) catalysis of olefin photoreactions. 9. Photobicyclization of .alpha.-, .beta.-, and .gamma.-alkenylallyl alcohols

  摘要：

  DOI：

  10.1021/ja00368a014

文献信息

• Olefin‐Supported Cationic Copper Catalysts for Photochemical Synthesis of Structurally Complex Cyclobutanes
  作者：Christopher S. Gravatt、Luis Melecio‐Zambrano、Tehshik P. Yoon

  DOI：10.1002/anie.202013067

  日期：2021.2.19

  The sole method available for the photocycloaddition of unconjugated aliphatic alkenes is the Cu‐catalyzed Salomon–Kochi reaction. The [Cu(OTf)]2⋅benzene catalyst that has been standard in this reaction for many decades, however, is air‐sensitive, prone to photodecomposition, and poorly reactive towards sterically bulky alkene substrates. Using bench‐stable precursors, an improved catalyst system with

  可用于非共轭脂肪烯烃光环加成的唯一方法是铜催化的 Salomon-Kochi 反应。然而，几十年来一直是该反应标准的[Cu(OTf)] 2 ·苯催化剂对空气敏感，易于光分解，并且对空间庞大的烯烃底物反应性差。使用台式稳定的前体，设计了一种具有优异反应性和光稳定性的改进催化剂体系，并显着扩大了底物范围。通过制备天然产物 sulcatine G 和 perforatol 的核心，突出了这种新催化剂用于制备空间拥挤环丁烷结构的实用性。
• Stereoselective Intramolecular Copper(I)-Catalyzed [2 + 2]- Photocycloadditions. Enantioselective Synthesis of (+)- and (-)-Grandisol
  作者：Klaus Langer、Jochen Mattay

  DOI：10.1021/jo00127a034

  日期：1995.11

  This work deals with copper(I)-catalyzed intramolecular [2 + 2]-photocycloadditions of 1,6-diene derivatives. The bridgehead carbons C-l and C-5 of the resulting bicyclo[3.2.0]heptanes are generated stereoselectively by using chiral starting material, chiral catalysts, or chiral auxiliaries. The irradiation of (S)-3 leads to enantiomerically pure 4 and 5 which opens a new synthetic route to enantiomerically pure (+)- and (-)-grandisol 9. The use of chiral copper complexes as catalysts delivers enantiomeric excesses below 5%. The reason for these small excesses is a low reactivity of the chiral copper complexes, as confirmed by CD-spectroscopic measurements. Malic acid or amino carboxylic acid derivatives as chiral auxiliaries yield the bicyclic alcohols 4 and 5 with enantiomeric excesses up to 15%. The employment of a chiral diol as an auxiliary delivers a chiral ketal 36, and the resulting ketone 7 exhibits enantiomeric excesses up to 60%.
• Polycyclic Cyclopropanes from Reactions of Alkene-Containing Fischer Carbene Complexes and Alkynes: A Formal Synthesis of (.+-.)-Carabrone
  作者：Thomas R. Hoye、James R. Vyvyan

  DOI：10.1021/jo00118a040

  日期：1995.6

  The polycyclic cyclopropanation reaction of several alkene-containing Fischer carbene complexes with various alkyne partners to provide bicyclo[4.1.0] enol ethers and ketones was examined. A number of features were probed, including the role of carbene donor substituent (amino vs alkoxy), the presence of one vs two pendant alkenes in the carbene complex, the level and sense of diastereoselectivity, and the impact of the substituents present on the alkyne partner. Relative configurations in cyclization products were established by H-1 NMR and difference NOE experiments. Using the above investigations as a guide, the tricyclic sesquiterpene lactone carabrone (5) was formally synthesized. The key cyclization of a symmetrical tetraene-containing carbene complex (8) with propyne provided ketone 42 in good yield as a single diastereomer. Six additional steps gave the tricyclic lactone 6, thus- constituting a formal total synthesis of carabrone (5). Notable features of the synthesis are that (i) the desymmetrizing cyclopropanation reaction between propyne and the symmetrical, tetraene-containing carbene complex is both efficient and highly diastereoselective, (ii) the alkenes remaining after the desymmetrizing cyclopropanation serve very effectively as protected carbonyl groups, and (iii) this work constitutes the first use of a Fischer carbene polycyclic cyclopropanation reaction in natural product synthesis.
• Chen, Ligong; Gill, G. Bryon; Pattenden, Gerald, Journal of the Chemical Society. Perkin transactions I, 1996, # 1, p. 31 - 44
  作者：Chen, Ligong、Gill, G. Bryon、Pattenden, Gerald、Simonian, Houri

  DOI：——

  日期：——
• Langer, Klaus; Mattay, Jochen; Heidbreder, Andreas, Liebigs Annalen der Chemie, 1992, # 3, p. 257 - 260
  作者：Langer, Klaus、Mattay, Jochen、Heidbreder, Andreas、Moeller, Manfred

  DOI：——

  日期：——