(E)-3-Methyl-2-octen-4-ol | 136707-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-Methyl-2-octen-4-ol
• 英文别名: (E)-3-methyloct-2-en-4-ol
• CAS: 136707-95-4
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: XRVYDGOUESSMCD-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (E)-3-Methyl-2-octen-4-ol 在 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2R*,4S*)-3-methylene-4-methoxy-2-(4'-phenyl-1',2',4'-triazolidine-3',5'-dion-1'-yl)-octane
  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
• 作为产物：
  描述：

  正丁基锂 、 反式-2-甲基-2-丁烯醛 以 四氢呋喃 为溶剂， 反应 4.0h， 以77%的产率得到(E)-3-Methyl-2-octen-4-ol
  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

• Cobalt-Catalyzed Intramolecular Silylperoxidation of Unsaturated Diisopropylsilyl Ethers
  作者：Jonathan P. Oswald、K. A. Woerpel

  DOI：10.1021/acs.joc.9b00642

  日期：2019.6.21

  A cobalt-catalyzed intramolecular silylperoxidation reaction was developed that allows for the conversion of unsaturated diisopropylsilyl ethers to 3-sila-1,2,4-trioxepanes. Reduction of the peroxide unit of the 3-sila-1,2,4-trioxepane yields six-membered ring diisopropylsilylene acetals.

  开发了钴催化的分子内甲硅烷基过氧化反应，可将不饱和二异丙基甲硅烷基醚转化为 3-sila-1,2,4-三氧杂环庚烷。 3-sila-1,2,4-三氧杂环己烷的过氧化物单元的还原产生六元环二异丙基亚甲硅基缩醛。
• One-flask, regiospecific conversions of allylic alcohols into 2-carbon-extended, conjugated dienoate esters. Use of a new sulfinyl orthoester
  作者：Gary H. Posner、R. David Crouch、Chris M. Kinter、Jean Christophe Carry

  DOI：10.1021/jo00025a008

  日期：1991.12

  Sixteen differently substituted primary and secondary allylic alcohols are shown to react with sulfinyl orthoacetate 1 at 100-degrees-C sequentially via a [3,3] sigmatropic rearrangement and then a beta-elimination of benzenesulfenic acid to form conjugated dienoate esters 5-13 in 45-95% yields. This one-flask, intramolecular carbon-carbon bond-forming process represents a simple and convenient method for regiospecific gamma-attachment of a two-carbon (ethoxycarbonyl)methylene unit via the synthetic equivalent of an S(N)2' process. Two examples are given in which rationally designed dienoates 20 and 24, prepared via this one-flask process and carrying a pendant alkene unit, undergo intramolecular 2 + 4 cycloaddition producing bicyclic cyclohexenes 21 and 25.
• Photo-oxidation of 2-(2-furyl)-1,3-dicarbonyl compounds
  作者：R. Antonioletti、F. Bonadies、S. Pesci、A. Scettri

  DOI：10.1016/s0040-4039(00)74826-x

  日期：1992.6

  A very efficient photo-sensitized oxidation of 2-(2-furyl)-1,3-dicarbonyl compounds 1 afford directly hydroperoxides 2 in stereoselective way. Compounds 2, easily isolated, can be conveniently employed in a selective epoxidation of trisubstituted allylic alcohols by a Sharpless-type procedure.
• Stereoselective Synthesis of Furans by the Pd-Catalyzed Oshima−Utimoto Reaction
  作者：Michael A. Evans、James P. Morken

  DOI：10.1021/ol051275s

  日期：2005.7.1

  The Pd-catalyzed coupling of acyclic allylic alcohols with vinyl ethers was examined and found to proceed with 2.5-10 mol % of catalyst and to provide cyclic acetals with good stereoselection. The reaction is tolerant of a number of functional groups and can be used to generate quaternary centers in a stereoselective fashion.