3-methoxynortricyclene | 21516-65-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-methoxynortricyclene
• CAS: 21516-65-4
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: GVZIVOAQRDBCNJ-RZUNNTJFSA-N

物化性质

• 沸点：
  40-70 °C(Press: 12 Torr)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  exo-3,4-diazotricyclo[4.2.1.0^2,5]nona-3,7-diene 在 Rh(pnen)3⁽³⁺⁾ 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 3-methoxynortricyclene
  参考文献：
  名称：

  Rh(III)-Photosensitized Interconversion of Norbornadiene and Quadricyclane

  摘要：

  The utility of two Rh(III) diimine complexes, Rh(phen)(3)(3+) and Rh(phi)(2)(phen)(3+) (phen = 1,10-phenanthroline, phi = 9,10-phenanthrenequinone diimine), as sensitizers for the interconversion of norbornadiene (N) and quadricyclane (Q) has been investigated using steady-state photochemical and laser flash photolysis (LFP) techniques. Irradiation of acetonitrile solutions of Rh(phen)(3)(3+) and N causes slow conversion to Q. The reaction is reversible; irradiation of Rh(phen)(3)(3+) in the presence of Q leads to N. Irradiation of acetonitrile solutions of Rh(phi)2(phen)3+ and Q yields N. However, this reaction is irreversible; irradiation of the Rh(In) complex in the presence of N fails to afford Q. Irradiation of methanol solutions of either Rh(III) complex in the presence of N or Q affords minor amounts of two methanol-C7 adducts but fails to quench the N-Q interconversion reaction. The results are consistent with N-Q interconversion via an exciplex intermediate. The Rh(III)-sensitized deazatization of two cyclic azoalkane derivatives (Azo-N, Azo-Q) of N and Q was also investigated. Deazatization was achieved by Rh(phen)(3)(3+) but not Rh(phi)(2)(phen)(3+) sensitization. The results are consistent with a mechanism involving triplet energy transfer, but the involvement of exciplex intermediates cannot be ruled out. Bimolecular rate constants for quenching of the Rh(III) excited states by N, Q, Azo-N, and Azo-Q were determined by LFP.

  DOI：

  10.1021/jp972007h

文献信息

• Addition reactions of alkenes with electronegatively substituted alcohols in the presence of xenon difluoride
  作者：Melvin L. Druelinger、Dale F. Shellhamer、Robert D. Chapman、Scott A. Shackelford、Maurice E. Riner、Steven L. Carter、Ryan P. Callahan、Cameron R. Youngstrom

  DOI：10.1039/a604677k

  日期：——

  The electrophilic reactivity of proposed alkoxyxenon fluoride (ROXeF) intermediates based on electronegatively substituted (polyfluorinated and polynitroaliphatic) alcohols has been characterized with model alkenes norbornene, 2-methylpent-1-ene and hex-1-ene. The alkoxyxenon fluorides can react as positive oxygen electrophiles—initially incorporating alkoxy substituents—or as apparent fluorine electrophiles—resulting in initial fluorine incorporation—depending on conditions. Efficient simple addition of poorly nucleophilic alcohols to norbornene was observed in certain systems. Selectivity between the various reaction paths (simple fluorination, alkoxyfluorination or alcohol addition) was observed to be a sensitive function of various reaction conditions, especially solvent, temperature and catalyst.

  根据电负性取代的（多氟化和多硝基脂肪族）醇，提出的醇氧氟氙（ROXeF）中间体的电亲反应性已通过模型烯烃如内苯、2-甲基戊-1-烯和己-1-烯进行表征。这些醇氧氟氙可作为正氧电亲体反应——最初引入醇氧取代基——或作为表观氟电亲体反应——导致初始氟的引入——具体取决于反应条件。在某些体系中，观察到欠亲核醇与内苯之间的高效简单加成。不同反应路径（简单氟化、醇氧氟化或醇加成）之间的选择性被认为是各种反应条件的敏感函数，特别是溶剂、温度和催化剂。
• Photoinduced addition of nucleophiles to bicyclo[2.2.1]hepta-2,5-diene
  作者：Paul G. Gassman、Kurt D. Olson

  DOI：10.1016/s0040-4039(00)81315-5

  日期：1983.1

  The 1-cyanonaphthalene photosensitized addition of water and methanol to the cation-radical of bicyclo[2.2.1]hepta-2,5-diene is described.

  描述了对双环[2.2.1]庚-2,5-二烯的阳离子自由基进行水和甲醇的1-氰基萘光敏加成。
• Electroorganic chemistry. X. Anodic allylic substitution
  作者：Tatsuya Shono、Akihiko Ikeda

  DOI：10.1021/ja00777a036

  日期：1972.11
• Stereospecific nucleophilic trapping of encounter complexes between photoexcited 1-cyanonaphthalene and norbornadiene
  作者：Hengxin Weng、Heinz D. Roth

  DOI：10.1002/(sici)1099-1395(199802)11:2<101::aid-poc978>3.0.co;2-g

  日期：1998.2
• Moss, Robert A.; Ma, Yan; Sauers, Ronald R., Journal of Organic Chemistry, 2004, vol. 69, # 11, p. 3628 - 3634
  作者：Moss, Robert A.、Ma, Yan、Sauers, Ronald R.、Madni, Mahvash

  DOI：——

  日期：——