(E)-2-methyl-6-(2'-methylphenyl)-2-heptene | 98039-30-6

• 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: (E)-2-methyl-6-(2'-methylphenyl)-2-heptene
• 英文别名: Benzene, 1-(1,5-dimethyl-4-hexenyl)-2-methyl-；1-methyl-2-(6-methylhept-5-en-2-yl)benzene
• CAS: 98039-30-6
• 化学式: C₁₅H₂₂
• 分子量: 202.34
• InChiKey: KILGTMHGYFPDSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-6-(2'-methylphenyl)-2-heptene 以 正戊烷 为溶剂， 反应 2.0h， 生成 (1aR,4S,4aS,6cR)-1,1,4,6c-Tetramethyl-1,1a,2,3,4,6a,6b,6c-octahydro-cyclopenta[g]cyclopropa[cd]pentalene 、 (2aS,3aS,6R,6cR)-3,3,6,6c-Tetramethyl-2a,3,3a,4,5,6,6b,6c-octahydro-cyclopenta[a]cyclopropa[gh]pentalene
  参考文献：
  名称：

  Synthetic studies on arene-olepin cycloadditions-VII:1 a three-step total synthesis of (±)-silphinene

  摘要：

  DOI：

  10.1016/s0040-4039(00)98120-6
• 作为产物：
  描述：

  6-甲基-5-庚烯-2-酮 、 2-溴甲苯 生成 (E)-2-methyl-6-(2'-methylphenyl)-2-heptene
  参考文献：
  名称：

  Synthetic studies on arene-olepin cycloadditions-VII:1 a three-step total synthesis of (±)-silphinene

  摘要：

  DOI：

  10.1016/s0040-4039(00)98120-6

文献信息

• Carbocationic Rearrangements of Silphinane Derivatives
  作者：Robert M. Coates、Jonathan Z. Ho、Michael Klobus、Lijuan Zhu

  DOI：10.1021/jo971579v

  日期：1998.12.1

  Solvolysis of silphin-1 alpha and -1 beta-yl mesylates (18 alpha-OMs and 18 beta-OMs) gave rise to mixtures of silphinene (4), bridgehead alcohol 22-OH (or its acetate), and alpha-terrecyclene (5) accompanied by trace amounts of isocomene (1) and modhephene (2). The 10(3) higher solvolysis rate determined for 18 alpha-OMs over its epimer signifies a concerted rearrangement to a more stable tertiary bridgehead carbocation (36) which undergoes a second rearrangement and elimination to alpha-terrecyclene (5) (see Scheme 5 in the paper). Isocomene and modhephene presumably arise from a minor competing pathway resulting from 7-->1 hydride shift to the silphin-7-yl ion (38 = 11) which partitions between methyl and cyclopentane ring rearrangements. Acetolysis of secosilphinyl nosylate 21 (X = ONs) is accompanied by pi participation leading directly to 38 and from there to a 2:1 mixture (6%) of isocomene and modhephene. TiCl4-mediated heterolysis of silphin-1 alpha-yl trifluoroacetate (18 alpha-O2CCF3) initiates a complex rearrangement pathway to 3-chloro-1,4,4,11-tetramethyltricyclo[5.3.1.0(3,8)]undecane (24). alpha-Terrecyclene (5) was converted to various oxygenated terrecyclane derivatives by dihydroxylation, hydroboration, and epoxidation (see Scheme 3 in the paper) and to its exocyclic isomer beta-terrecyclene (34, see Scheme 4 in the paper). The observed rearrangements of the silphinyl mesylates (see Scheme 5 in the paper) afford chemical precedent for a biogenetic pathway that links terrecyclanes (e.g. quadrone), isocomene, and modhephene to the silphinane family of cyclopentanoid sesquiterpenes formally derivable from caryophyllene (see Scheme 1 in the paper).
• Synthetic studies on arene-olepin cycloadditions-VII:1 a three-step total synthesis of (±)-silphinene
  作者：Paul A. Wender、Robert J. Ternansky

  DOI：10.1016/s0040-4039(00)98120-6

  日期：1985.1