[9]metacyclophane | 7198-61-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: [9]metacyclophane
• 英文别名: [9]-m-cyclophane；<9>Metacyclophane；Bicyclo[9.3.1]pentadeca-1(15),11,13-triene
• CAS: 7198-61-0
• 化学式: C₁₅H₂₂
• 分子量: 202.34
• InChiKey: BGMOKWMQFWOSEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1,3-二氯苯 以9%的产率得到
  参考文献：
  名称：

  TAMAO K.; KODAMA S.; NAKATSUKA T.; KISO Y.; KUMADA M., J. AMER. CHEM. SOC. , 1975, 97, NO 15, 4405-4406

  摘要：

  DOI：

文献信息

• Parallel mechanisms for the cycloaromatization of enyne allenes †
  作者：Thomas S. Hughes、Barry K. Carpenter

  DOI：10.1039/a904369a

  日期：——

  The Myers–Saito cycloaromatization of enyne allenes is proposed to consist of two parallel mechanisms, one involving a biradical and the other with dipolar character. MCSCF calculations suggest that a nonplanar cyclic allene could be fairly close in enthalpy to the biradical, while the planar zwitterion originally proposed as a possible second intermediate is in fact a transition state for the interconversion

  迈恩斯-塞托烯烯的环芳烃化被认为是由两个平行的机制组成，一个涉及双自由基，另一个具有偶极特性。MCSCF计算表明，非平面环状烯与双自由基的焓可能相当接近，而最初提议作为可能的第二中间体的平面两性离子实际上是两个对映体环状烯的互变的过渡态。竞争性诱捕实验排除了单一中间体的存在，并且与平行途径的参与一致。（Z）-庚-1,2,4-三烯-6-炔在环戊二烯中的反应产生了不可分离的两种四环产物的混合物，其结构通过2-D NMR得以阐明。
• Synthesis of [<i>n</i>]- and [<i>n</i>.<i>n</i>]Cyclophanes by Using Suzuki−Miyaura Coupling
  作者：Beverly B. Smith、Darron E. Hill、T. Ashton Cropp、Rosa D. Walsh、David Cartrette、Sherry Hipps、Amy M. Shachter、William T. Pennington、William R. Kwochka

  DOI：10.1021/jo025509m

  日期：2002.7.1

  Reaction of the bis-9-BBN adduct of several dienes with 1,3-dibromobenzene via Suzuki coupling leads to a series of [n]metacyclophanes ranging in size from 10 to 17 atom members. In each case, two carbon-carbon bonds are formed in one reaction vessel. However, when the bis-9-BBN adduct of 1,5-hexadiene is coupled with a variety of aryl dihalides, larger [n.n]cyclophanes were formed in preference to the [n]cyclophanes. Four carbon-carbon bonds are formed in this instance. Single-crystal X-ray analyses of these [n.n]cyclophanes reveal interestingly shaped molecules with large cavities.
• One-step preparation of metacyclophanes and (2,6)pyridinophanes by nickel-catalzyed Grignard cyclocoupling
  作者：Kohei Tamao、Shunichi Kodama、Takuo Nakatsuka、Yoshihisa Kiso、Makoto Kumada

  DOI：10.1021/ja00848a050

  日期：1975.7
• Arenes disubstituted with primary alkyl groups from xylylene dianions
  作者：Robert B. Bates、Craig A. Ogle

  DOI：10.1021/jo00141a027

  日期：1982.9
• BATES, R. B.;OGLE, C. A., J. ORG. CHEM., 1982, 47, N 20, 3949-3952
  作者：BATES, R. B.、OGLE, C. A.

  DOI：——

  日期：——