p-chlorobenzylidene-DL-piperitone | 131956-49-5

• 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: p-chlorobenzylidene-DL-piperitone
• 英文别名: 3-[(E)-2-(4-chlorophenyl)ethenyl]-6-propan-2-ylcyclohex-2-en-1-one
• CAS: 131956-49-5
• 化学式: C₁₇H₁₉ClO
• 分子量: 274.79
• InChiKey: FYPFHYOAISUUJH-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  p-chlorobenzylidene-DL-piperitone 以 苯 为溶剂， 反应 36.0h， 以71%的产率得到6-Chloro-3-isopropyl-2,3-dihydro-1H-phenanthren-4-one
  参考文献：
  名称：

  Photochemistry of benzylidene-d,l-piperitones in solution and the melt phase

  摘要：

  The solution- and melt-phase photochemistry of four trans-benzylidene-d,l-piperitones (1) has been investigated under a variety of conditions. The 1 undergo trans reversible cis isomerization to establish a quasi photostationary state. Further irradiation leads to 2 via oxidative ring closure. Conspicuously absent are dimers (obtained upon irradiation of the neat crystals) and the plausible Norrish Type II photoproducts, 3. Although 1c yields 2c, no evidence for the alternative cyclization route to 2a (requiring loss of HCl) has been observed. Rationalizations for the transformations are presented. The structure of 2b has been determined unambiguously from X-ray crystallographic analysis.

  DOI：

  10.1021/jo00027a049

文献信息

• Studies in crystal engineering: topochemical photodimerization and structure of <i>p</i>-chlorobenzylidene-<scp>DL</scp>-piperitone
  作者：P. Venugopalan、K. Venkatesan

  DOI：10.1107/s0108768190007029

  日期：1990.12.1

  3-(p-Chlorophenylvinyl)-6-isopropyl-2-cyclohexen-1-one, C17H19ClO, M(r) = 274.7, triclinic, P1BAR, a = 6.636 (1), b = 10.537 (2), c = 10.811 (3)-angstrom, alpha = 95.31 (2), beta = 92.60 (2), gamma = 100.66 (2)-degrees, V = 738.2 (2)-angstrom-3, Z = 2, D(m) = 1.23, D(x) = 1.236 Mg m-3, Cu K-alpha, lambda = 1.5418-angstrom, mu = 2.09 mm-1, F(000) = 292, T = 298 K, R = 0.050 for 2220 observed reflections. The title compound undergoes a topochemical photodimerization giving an anti head-to-tail dimer instead of the syn head-to-head dimer expected on the basis of the ability of the chloro group to steer beta-type packing. There are no significant Cl...Cl intermolecular interactions. Possible reasons for the observed alpha-type packing of benzylidenepiperitones are advanced. The low dimer yield is also rationalized.