trans-(7-methyl-octa-1,6-dienyl)-benzene | 128900-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-(7-methyl-octa-1,6-dienyl)-benzene
• 英文别名: (E)-1-phenyl-7-methyl-1,6-octadiene；(7-methylocta-1,6-dienyl)benzene；[(1E)-7-methylocta-1,6-dienyl]benzene
• CAS: 128900-82-3
• 化学式: C₁₅H₂₀
• 分子量: 200.324
• InChiKey: SENUOBRKZBXPIH-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  trans-(7-methyl-octa-1,6-dienyl)-benzene 在 (bicyclo[2.2.1]hepta-2,5-diene)-(2,4-pentanedionato)-rhodium 、 1-(2-二苯基庚基1萘酚)硫酸甲基酯 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 (1R,2R)-7-methyl-1-phenyl-oct-6-ene-1,2-diol
  参考文献：
  名称：

  Rh-Catalyzed Enantioselective Diboration of Simple Alkenes:  Reaction Development and Substrate Scope

  摘要：

  The rhodium-catalyzed reaction between bis(catecholato)diboron and simple alkenes results in the syn addition of the diboron across the alkene. The resulting 1,2-bis(boronate) is subsequently oxidized to provide the 1,2-diol. In the presence of enantiomerically enriched Quinap ligand, high enantioselection in the diboration can be achieved. The reaction is highly selective for trans- and trisubstituted alkenes and can be selective for some monosubstituted alkenes as well. The development of this reaction is described as is the substrate scope and experiments that are informative about the reaction mechanism and competing pathways.

  DOI：

  10.1021/jo051651m
• 作为产物：
  描述：

  6-methylhept-5-en-1-ol 在 草酰氯 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 反应 2.83h， 生成 trans-(7-methyl-octa-1,6-dienyl)-benzene
  参考文献：
  名称：

  Intramolecular anodic olefin coupling reactions: a useful method for carbon-carbon bond formation

  摘要：

  The utility of intramolecular anodic olefin coupling reactions for effecting carbon-carbon bond formation has been examined. All of the successful cyclizations studied utilized either an alkyl or silyl enol ether as one of the participating olefins. The enol ethers could be coupled to simple alkyl olefins, styrenes, and allylsilanes in isolated yields ranging from 57 to 84%. The reactions were found to be effective for generating both five- and six-membered rings. The best conditions for cyclization utilized a reticulated vitreous carbon anode, constant-current conditions in an undivided cell, and a lithium perchlorate in either 50% methanol/tetrahydrofuran or 20% methanol/dichloromethane electrolyte solution. The use of an allylsilane as one of the participating olefins allowed for the regiospecific formation of olefinic products. In addition to the olefinic products, these reactions produced a small amount of a cyclized ether product in which the silyl group had not been eliminated. Deuterium-labeling studies showed that at least half of this ether byproduct arose from intramolecular migration of the methoxy group that was initially part of the starting enol ether to the carbon-beta to the silyl group. Intramolecular migration reactions of this type were found to participate in a number of the reported cyclization reactions.

  DOI：

  10.1021/ja00019a038

文献信息

• Addition of ArSSAr to dienes via intramolecular C–C bond formation initiated by a catalytic amount of ArS+
  作者：Kouichi Matsumoto、Shunsuke Fujie、Seiji Suga、Toshiki Nokami、Jun-ichi Yoshida

  DOI：10.1039/b910821a

  日期：——

  A catalytic amount of electrochemically generated “ArS+” (“ArS+” = ArS(ArSSAr)+) initiates a cation chain reaction of dienes that involves the addition of ArSSAr associated with stereoselective intramolecular carbon–carbon bond formation, and the direct (in-cell) electrolysis of a mixture of a diene and ArSSAr with a catalytic amount of electricity also effectively initiates the reaction.

  通过电化学方法生成的催化量的“ArS+”（“ArS+” = ArS(ArSSAr)+）启动了二烯的阳离子链反应，该反应涉及与立体选择性分子内碳-碳键形成相关的ArSSAr加成，并且通过在混合物中直接（在电池内）电解二烯和ArSSAr，并施加催化量的电能，也能有效地引发该反应。
• MOELLER, KEVIN D.;MARZABADI, MOHAMMAD R.;NEW, DALLAS G.;CHIANG, MICHAEL Y+, J. AMER. CHEM. SOC., 112,(1990) N6, C. 6123-6124
  作者：MOELLER, KEVIN D.、MARZABADI, MOHAMMAD R.、NEW, DALLAS G.、CHIANG, MICHAEL Y+

  DOI：——

  日期：——
• Rh-Catalyzed Enantioselective Diboration of Simple Alkenes:  Reaction Development and Substrate Scope
  作者：Stéphane Trudeau、Jeremy B. Morgan、Mohanish Shrestha、James P. Morken

  DOI：10.1021/jo051651m

  日期：2005.11.1

  The rhodium-catalyzed reaction between bis(catecholato)diboron and simple alkenes results in the syn addition of the diboron across the alkene. The resulting 1,2-bis(boronate) is subsequently oxidized to provide the 1,2-diol. In the presence of enantiomerically enriched Quinap ligand, high enantioselection in the diboration can be achieved. The reaction is highly selective for trans- and trisubstituted alkenes and can be selective for some monosubstituted alkenes as well. The development of this reaction is described as is the substrate scope and experiments that are informative about the reaction mechanism and competing pathways.
• Intramolecular anodic olefin coupling reactions: a useful method for carbon-carbon bond formation
  作者：Christine M. Hudson、Mohammad R. Marzabadi、Kevin D. Moeller、Dallas G. New

  DOI：10.1021/ja00019a038

  日期：1991.9

  The utility of intramolecular anodic olefin coupling reactions for effecting carbon-carbon bond formation has been examined. All of the successful cyclizations studied utilized either an alkyl or silyl enol ether as one of the participating olefins. The enol ethers could be coupled to simple alkyl olefins, styrenes, and allylsilanes in isolated yields ranging from 57 to 84%. The reactions were found to be effective for generating both five- and six-membered rings. The best conditions for cyclization utilized a reticulated vitreous carbon anode, constant-current conditions in an undivided cell, and a lithium perchlorate in either 50% methanol/tetrahydrofuran or 20% methanol/dichloromethane electrolyte solution. The use of an allylsilane as one of the participating olefins allowed for the regiospecific formation of olefinic products. In addition to the olefinic products, these reactions produced a small amount of a cyclized ether product in which the silyl group had not been eliminated. Deuterium-labeling studies showed that at least half of this ether byproduct arose from intramolecular migration of the methoxy group that was initially part of the starting enol ether to the carbon-beta to the silyl group. Intramolecular migration reactions of this type were found to participate in a number of the reported cyclization reactions.