endo-3,3-diphenyltricyclo<3.2.1.0^2,4>oct-6-ene | 54163-87-0

• 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: endo-3,3-diphenyltricyclo<3.2.1.0^2,4>oct-6-ene
• 英文别名: 3,3-Diphenyltricyclo<3.2.1.0^2,4>octen；endo-3,3-diphenyltricyclo[3.2.1.0^2,4]oct-6-ene；endo-3,3-Diphenyltricyclo[3.2.1.0^2,4^]oct-6-ene；(1R,2S,4R,5S)-3,3-diphenyltricyclo[3.2.1.02,4]oct-6-ene
• CAS: 54163-87-0
• 化学式: C₂₀H₁₈
• 分子量: 258.363
• InChiKey: FQZNJNRELMUCBK-FDCRZUCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  endo-3,3-diphenyltricyclo<3.2.1.0^2,4>oct-6-ene 以32%的产率得到
  参考文献：
  名称：

  PEERAN, MEHBOOB;WILT, JAMES W.;RAMAKRISHNAN, SUBRAMANIAN;CRUMRINE, DAVID +, J. CHEM. SOC. CHEM. COMMUN.,(1989) N4, C. 1906-1907

  摘要：

  DOI：
• 作为产物：
  描述：

  (3aS,4R,7S,7aS,8S)-8-tert-Butoxy-3,3-diphenyl-3a,4,7,7a-tetrahydro-3H-4,7-methano-indazole 在 甲基碘化镁 、 高氯酸 、 溶剂黄146 作用下， 生成 endo-3,3-diphenyltricyclo<3.2.1.0^2,4>oct-6-ene
  参考文献：
  名称：

  3,3-Diaryltricyclo[3.2.1.02,4]octanes. IV. Addition of diphenyldiazomethane to 7-tert-butoxynorbornadiene. Formation of exo- and endo-3,3-diphenyltricyclo[3.2.1.02,4]octene derivatives

  摘要：

  DOI：

  10.1021/jo00896a008

文献信息

• 13C NMR studies of some tricyclo[3.2.1.02,4]octanes
  作者：James W. Wilt、Mehboob Peeran、Subramanian Ramakrishnan、David S. Crumrine

  DOI：10.1002/mrc.1260270405

  日期：1989.4

  and endo‐3,3‐diphenyltricyclo[3.2.1.02,4]octanes are reported. Comparisons with the parent exo‐ and endo‐tricyclo[3.2.1.02,4]octanes and with bicyclo[2.2.1]heptanes show that most of the chemical shifts are additive. Substituent effect constants are presented for the tricyclo[3.2.1.02,4]octyl system. Pronounced deshielding effects are seen in the endo series for C‐6 and −7 of the alkene endo‐3,3‐diphenyltricyclo[3

  报道了一系列外型和内型 3,3-二苯基三环 [3.2.1.02,4] 辛烷的 13C NMR 化学位移。与母体外型和内型三环 [3.2.1.02,4] 辛烷以及双环 [2.2.1] 庚烷的比较表明，大多数化学位移是加性的。为三环[3.2.1.02,4]辛基体系提供了取代基效应常数。在烯烃内-3,3-二苯基三环[3.2.1.02,4]oct-6-烯、环氧化物内-3,3-二苯基三环[3.2]的C-6和-7的内系列中可以看到明显的去屏蔽效应.1.02,4]octan-6,7-exo-oxide 和四环 exo-3,3-diphenyltetracyclo[3.3.1.02,406,8]nonane。C-3 和 -8 的化学位移可用于诊断内取代与外取代。
• ? Participation in addition reactions of endo-3,3-diphenyltricyclo[3.2.1.02,4]oct-6-ene
  作者：Mehboob Peeran、James W. Wilt、Subramanian Ramakrishnan、David S. Crumrine

  DOI：10.1039/c39890001906

  日期：——

  Radical initiated LRAMERO (long range aryl migration coupled with electrophilic ring opening) is one example of π participation occurring from the syn phenyl ring of (1) in both electrophilic and radical addition reactions.

  自由基引发的LRAMERO（长距离芳基迁移与亲电子开环偶联）是在亲电子和自由基加成反应中由（1）的合成苯环发生的π参与的一个实例。
• Aryl .pi. participation in additions and solvolyses of endo-3,3-diphenyltricyclo[3.2.1.02,4]oct-6-ene and -oct-6-yl systems
  作者：Mehboob Peeran、James W. Wilt、Ramakrishnan Subramanian、David S. Crumrine

  DOI：10.1021/jo00053a037

  日期：1993.1

  The influence of phenyl pi electrons on the strategically located double bond of the endo-3,3-diphenyltricyclo[3.2.1.0(2,4)]oct-6-ene (1) during cycloaddition, electrophilic addition, epoxidation, reduction, cyclopropanation, and radical addition has been investigated both through product identification and relative rate studies. Similar additions to the isomeric exo-3,3-diphenyltricyclo[3.2.1.0(2,4)]oct-6-ene (2) serve as a mechanistic contrast to the reactions of 1. This is the first system that appears to demonstrate radical-initiated LRAMERO (long-range aryl migration with electrocyclic ring opening). Solvolyses of the exo and endo tosylates derived from 1 are also influenced by the underlying phenyl group.
• endo-3,3-Diphenyltricyclo[3.2.1.02,4]oct-6-ene
  作者：M. Peeran、J. W. Wilt、E. J. Zaluzec、S. F. Pavkovic

  DOI：10.1107/s0108270195000771

  日期：1995.5.15

  The main feature in the title compound, C20H18, is the system of fused three-, five- and six-membered rings. The two phenyl substituents are bonded to one C atom of the three-membered ring and that ring adopts an endo conformation relative to the larger rings. This results in a phenyl-group atom being close to the diene bond in the fused rings. The contact distances are 2.912(4) and 2.952 (3) Angstrom. The plane of this phenyl group is nearly parallel to the diene bond. Planes of the two phenyl rings make an angle of 76.1 (2)degrees.
• Stereochemical investigations: reduction of syn-8-chloro- and cleavage of anti-8-tert-butoxy-endo-3,3-diphenyltricyclo[3.2.1.02,4]oct-6-enes
  作者：Mehboob Peeran、James W. Wilt、Ramakrishnan Subramanian、David S. Crumrine

  DOI：10.1021/jo00005a052

  日期：1991.3