1-tert-butylcycloheptene | 937-03-1

• 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: 1-tert-butylcycloheptene
• 英文别名: 1-t-butyl-cycloheptene；1-t-butylcycloheptene；t-butyl-cycloheptene；1-tert.-Butyl-cyclohept-1-en；1-tert-Butyl-cyclohepten；t-Butylcycloheptene
• CAS: 937-03-1
• 化学式: C₁₁H₂₀
• 分子量: 152.28
• InChiKey: UWBJPUXTTHBACI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  1-tert-butylcycloheptene 在 potassium tert-butylate 、 甲基锂 、 对甲苯磺酸 作用下， 以 正戊烷 为溶剂， 生成 1-tert-butyl-1,3-cyclooctadiene
  参考文献：
  名称：

  小环环状枯草烯：动力学稳定的八元环亚丙基的合成

  摘要：

  从环庚酮分四步制备1-叔丁基-1，2-环戊二烯，发现对二聚反应稳定。

  DOI：

  10.1016/s0040-4039(00)85036-4
• 作为产物：
  描述：

  8,8-dibromo-1-tert-butylbicyclo<5.1.0>octane 在 甲基锂 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 氘代氯仿 、 正戊烷 为溶剂， 反应 0.75h， 生成 1-tert-butylcycloheptene
  参考文献：
  名称：

  Cumulene photochemistry: photoreactions of a strained 1,2-cyclooctadiene

  摘要：

  The singlet and triplet photoreactions of 1-tert-butyl-1,2-cyclooctadiene (1) are described. This is the first example of an isolable eight-membered ring allene and is predicted to have a bent allenic unit. Triplet reactions of 1 are phase dependent. Benzene-sensitized irradiation affords products of hydrogen abstraction at tert-butyl or ring carbons in vapor phase or solution phase, respectively. Direct irradiation of thoroughly degassed pentane solutions at 254 nm affords primarily 3-tert-butylbicyclo[3.3.0]oct-2-ene and other products that are attributed to initial excited-state 1,2-hydrogen migration to a vinylcarbene. Independent generation of this vinylcarbene gives a similar collection of products, which include an isolable bicyclo[5.1.0]oct-1(8)-ene. Irradiation of 1 in oxygenated solutions yields tert-butylcycloheptene (15), apparently through loss of carbon monoxide from an intermediate cyclopropanone. Oxidation of 1 with m-CPBA also leads efficiently to 15.

  DOI：

  10.1021/jo00022a029

文献信息

• Anhydrous ferric chloride dispersed on silica gel induced ring enlargement of tertiary cycloalkanols. II : a convenient homologation of cycloalkanones, preparation of spiro systems and propella -γ-lactones
  作者：A. Fadel、J. Salaun

  DOI：10.1016/s0040-4020(01)96528-7

  日期：1985.1

  The reagent obtained by mixing anhydrous FeCl3 and silica gel induced, in the lack of any solvent, dehydration of tertiary cycloalkanols, specific C4→C5 and C5 →C6 enlargement, formation of spiro compounds and propella-γ- lactones and cleavage of tetrahydropyranyl ethers.

  通过在无溶剂的情况下将无水FeCl 3和硅胶混合得到的试剂，导致叔环链烷醇脱水，C 4 →C 5和C 5 →C 6增大，形成螺环化合物和螺旋桨-γ-内酯，四氢吡喃基醚的裂解。
• Novel Catalytic Kinetic Resolution of Racemic Epoxides to Allylic Alcohols
  作者：Arnaud Gayet、Sophie Bertilsson、Pher G. Andersson

  DOI：10.1021/ol025983e

  日期：2002.10.1

  [formula: see text] The kinetic resolution of racemic epoxides via catalytic enantioselective rearrangement to allylic alcohols was investigated. Using the Li-salt of (1S,3R,4R)-3-(pyrrolidinyl)methyl-2-azabicyclo [2.2.1] heptane 1 as catalyst allowed both epoxides and allylic alcohols to be obtained in an enantioenriched form.

  研究了外消旋环氧化物通过催化对映选择性重排为烯丙基醇的动力学拆分。使用（1S，3R，4R）-3-（吡咯烷基）甲基-2-氮杂双环[2.2.1]庚烷1的锂盐作为催化剂，可以得到对映体富集形式的环氧化物和烯丙基醇。
• Ranganayakulu, K.; Vasumathi Devi, M.; Balaji Rao, R., Canadian Journal of Chemistry, 1980, vol. 58, # 14, p. 1484 - 1489
  作者：Ranganayakulu, K.、Vasumathi Devi, M.、Balaji Rao, R.、Rajeswari, K.

  DOI：——

  日期：——
• η³-Allylpalladium Complexes from Medium-Ring Cycloalkenes
  作者：Jean-Marie Rosset、Matthew P. Glenn、John D. Cotton、Anthony C. Willis、Colin H. L. Kennard、Karl A. Byriel、Bruce H. Riches、William Kitching

  DOI：10.1021/om971132c

  日期：1998.5.1

  The dimeric eta(3)-allylpalladium chloride complexes formed from various cycloalkenes (C-7-C-13) and some methyl-and tert-butyl-substituted cycle alkenes have be en characterized by H-1 and C-13 NMR spectroscopy and in selected cases by X-ray crystallography. The formation of syn and anti isomers in the larger ring systems is demonstrated, and complexes with a rearranged ring system are formed from tert-butylcyclodecene and tert-butylcyclododecene. The sesquiterpene, carophyllene, is shown to form an eta(3)-allyl exocyclic complex, exclusively from the (E)-double bond. Cis and trans isomers, with respect to allyl group orientation in these halo-bridged dimers, have been identified by low-temperature (190K) NMR spectroscopy, and their interconversion (Delta G(double dagger) approximate to 11 kcal/mol) is considered to involve a "cubic" eta(3)-allylpalladium chloride tetramer.
• Regioselective Formation of Cyclic and Allylic Hydroperoxides
  作者：Manolis Stratakis、Michael Orfanopoulos

  DOI：10.1080/00397919308009797

  日期：1993.2

  A regioselective photosensitized oxygenation is reported for the preparation of cyclic and allylic hydroperoxides.