3-benzylidene camphor | 36275-29-3

• 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-benzylidene camphor
• 英文别名: (1S,4R)-1,7,7-Trimethyl-3-(phenylmethylene)bicyclo[2.2.1]heptan-2-one；(1S,4R)-3-benzylidene-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• CAS: 36275-29-3
• 化学式: C₁₇H₂₀O
• 分子量: 240.345
• InChiKey: OIQXFRANQVWXJF-WMLDXEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  3-benzylidene camphor 在 三甲基氯硅烷 、 sodium 作用下， 生成 (1R,3R,4R,1'S,2'R,1''R,3''S,4''R)-3,3''-(1',2'-diphenylethylene)-bis-(1,7,7-trimethyl)bicyclo-[2.2.1]heptan-2-one 、 (1R,3R,4R,1'R,2'R,1''R,3''R,4''R)-3,3''-(1',2'-diphenylethylene)-bis-(1,7,7-trimethyl)bicyclo-[2.2.1]heptan-2-one
  参考文献：
  名称：

  Two Related Benzylcamphor Dimers

  摘要：

  The crystal structures of two related dimeric 3-benzyl-camphors, namely, (1R,3R,4R,1'R,3'R,4'R)-3,3'-[(1R,2R)-1,2-diphenylethylene]bis(1,7,7-trimethylbicyclo[2.2.1]- heptan-2-one), (1), and (1R,3R,4R, 1'R,3'S,4'R)-3,3'- [(1R,2S)-1,2-diphenylethylene] bis(1,7,7-trimethylbicyclo-[2.2.1]heptan-2-one), (2), both C34H42O2, are reported. Compound (1) possesses C-2 molecular symmetry; it adopts a conformation in the crystal in which the two phenyl rings are gauche with respect to one another and anti to the C3-C4 bond (terpene numbering) of the camphor ring system. Compound (2) lacks a molecular C-2 axis of symmetry; it adopts a conformation in the crystal where the two phenyl rings are anti with respect to one another, and in which one phenyl ring is partially in the endo cavity of the camphor ring system. In both compounds, C3 of both camphor ring systems (terpene numbering) is distorted to trigonal pyramidal from tetrahedral; the C-C-C bond angles about C3 in both camphor rings are considerably expanded from idealized tetrahedral values and the dihedral angle between the benzyl C atom and the carbonyl O atom is reduced from the idealized value of 60 degrees to less than 48 degrees.

  DOI：

  10.1107/s0108270197000371

文献信息

• Two Related Benzylcamphor Dimers
  作者：I.-H. Suh、S. Choi、D. E. Lewis、W. P. Jensen

  DOI：10.1107/s0108270197000371

  日期：1997.7.15

  The crystal structures of two related dimeric 3-benzyl-camphors, namely, (1R,3R,4R,1'R,3'R,4'R)-3,3'-[(1R,2R)-1,2-diphenylethylene]bis(1,7,7-trimethylbicyclo[2.2.1]- heptan-2-one), (1), and (1R,3R,4R, 1'R,3'S,4'R)-3,3'- [(1R,2S)-1,2-diphenylethylene] bis(1,7,7-trimethylbicyclo-[2.2.1]heptan-2-one), (2), both C34H42O2, are reported. Compound (1) possesses C-2 molecular symmetry; it adopts a conformation in the crystal in which the two phenyl rings are gauche with respect to one another and anti to the C3-C4 bond (terpene numbering) of the camphor ring system. Compound (2) lacks a molecular C-2 axis of symmetry; it adopts a conformation in the crystal where the two phenyl rings are anti with respect to one another, and in which one phenyl ring is partially in the endo cavity of the camphor ring system. In both compounds, C3 of both camphor ring systems (terpene numbering) is distorted to trigonal pyramidal from tetrahedral; the C-C-C bond angles about C3 in both camphor rings are considerably expanded from idealized tetrahedral values and the dihedral angle between the benzyl C atom and the carbonyl O atom is reduced from the idealized value of 60 degrees to less than 48 degrees.