exo-6-phenylbicyclo[3.1.0]hexane | 58647-76-0

• 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: exo-6-phenylbicyclo[3.1.0]hexane
• CAS: 58647-76-0
• 化学式: C₁₂H₁₄
• 分子量: 158.243
• InChiKey: ITWNLZAGIUPXAK-GDNZZTSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  溶剂黄146 、 exo-6-phenylbicyclo[3.1.0]hexane 、 对甲苯磺酸 、 乙酸酐 生成 rac-cyclopentyl(phenyl)methyl acetate
  参考文献：
  名称：

  CREARY X., J. ORG. CHEM., 1980, 45, NO 23, 4653-4659

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-6-phenylhex-5-enyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 四甲基乙二胺 、 仲丁基锂 、 鹰爪豆碱 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以93%的产率得到exo-6-phenylbicyclo[3.1.0]hexane
  参考文献：
  名称：

  (−)-Sparteine-Mediated Asymmetric Intramolecular Carbolithiation of Alkenes: Synthesis of Enantiopure Cyclopentanes with Three Consecutive Stereogenic Centers

  摘要：

  An asymmetric intramolecular carbolithiation reaction was developed by combining the (-)-sparteine-mediated enantiotopos-differentiating deprotonation and the anionic 5-exo-trig cyclization. Achiral 6-phenyl-hex-5-enyl carbamates were efficiently cyclized furnishing regio-, diastereo- (dr > 99:1),and enantioselectively (er >98:2) 1,2-trans-substituted cyclopentanes. The intermediate primary benzylic Lithium-carbanion pairs were - in spite of their configurative lability - diastereoselectively substituted by versatile electrophiles creating a third consecutive stereogenic center. Additionally, some 4-functionalized 6-phenylhex-5-enyl carbamates were also cyclized in high yield to provide enantiomericaliy pure cyclopentanes incorporating three adjacent stereogenic centers.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<1860::aid-hlca1860>3.0.co;2-8

文献信息

• Iron Lewis acid catalyzed reactions of phenyldiazomethane and olefins: Formation of cyclopropanes with very high cis selectivity
  作者：William J. Seitz、M.Mahmun Hossain

  DOI：10.1016/s0040-4039(00)78343-2

  日期：1994.10

  The iron Lewis acid, [(η5-C5H5)Fe(CO)2(THF)]+ (1) catalyzes the cyclopropanation reaction of phenyldiazomethane with olefins to provide cis cyclopropanes in high selectivity.

  铁路易斯酸，[（η 5 -C 5 H ^ 5）的Fe（CO）2（THF）] +（1）催化phenyldiazomethane与烯烃，以提供环丙烷化反应的顺式环丙烷在高选择性。
• Unconjugated arylcyclopropanes. Acid-catalyzed addition of acetic acid to highly hindered arylcyclopropanes
  作者：Xavier Creary

  DOI：10.1021/jo01311a021

  日期：1980.11
• Enantioselective carbanion cyclization of 5-alkenyl carbamates induced by asymmetric lithiation with s-butyllithium/(−)-sparteine system
  作者：Katsuhiko Tomooka、Nobuyuki Komine、Tomoya Sasaki、Hideo Shimizu、Takeshi Nakai

  DOI：10.1016/s0040-4039(98)02233-3

  日期：1998.12

  Treatment of (E)-6-phenyl-5-hexenyl carbamates with s-BuLi /(-)-sparteine is shown to afford the trans-1,2-disubstituted cyclopentane derivatives in high % ee, along with the bicyclo[3.1.0]hexanes (bicyclization products). (C) 1998 Elsevier Science Ltd. All rights reserved.