(2E,4E)-2,4-dibenzylidene-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one | 3016-20-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: (2E,4E)-2,4-dibenzylidene-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one
• 英文别名: 2(E),4(E)-dibenzylidenetropanone；2E,4E-dibenzylidenetropinone；2,4-Bibenzylidentropinon；2,4-Dibenzyliden-tropinon；2,4-dibenzylidene-8-methyl-nortropan-3-one；trans-trans-2,4-Dibenzylidentropinon；2,4-dibenzylidene-tropan-3-one；2,4-Dibenzyliden-tropan-3-on；(2E,4E)-2,4-dibenzylidene-8-methyl-8-azabicyclo[3.2.1]octan-3-one
• CAS: 3016-20-4
• 化学式: C₂₂H₂₁NO
• 分子量: 315.415
• InChiKey: UYTWVEVNIDBOOP-JSAVKQRWSA-N

物化性质

• 熔点：
  153 °C
• 沸点：
  509.8±50.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E)-2,4-dibenzylidene-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one 在 盐酸 、 汞 、 锌 作用下， 以 1,4-二氧六环 为溶剂， 生成 (1R,4R,5S)-2,4-Dibenzyl-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene
  参考文献：
  名称：

  Synthesis and evaluation of a series of tropane analogues as novel vesicular monoamine transporter-2 ligands

  摘要：

  A series of tropane derivatives has been synthesized as lobelane analogues and evaluated for their binding affinity at the vesicular monoamine transporter-2 (VMAT2), and at alpha 4 beta 2* and alpha 7* nicotinic acetylcholine receptors. The trop-2-ene analogues 4a and 4b exhibited good affinity and high selectivity for VMAT2. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.032
• 作为产物：
  描述：

  托品酮 在 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正庚烷 、 乙基苯 为溶剂， 反应 6.0h， 生成 (2E,4E)-2,4-dibenzylidene-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one
  参考文献：
  名称：

  The Preparation of 2‐Arylmethylidene‐8‐methyl‐8‐azabicyclo[3.2.1]octan‐3‐ones

  摘要：

  An efficient and versatile two-step synthesis of 2-arylmethylidene-8-methyl-8-azabicyclo[3.2.1]octane-3-ones, via mono aldol condensation of tropinone with a variety of aryl aldehydes followed by pTsOH-catalyzed dehydration, is described.

  DOI：

  10.1081/scc-120037905

文献信息

• SYNTHESIS OF 2,4-DISUBSTITUTED NORTROPINONE DERIVATIVES BY ALDOL CONDENSATION
  作者：Dai-Il Jung、Chil-Sung Park、Yong-Hwan Kim、Do-Hun Lee、Yong-Gyun Lee、Yu-Mi Park、Soon-Kyu Choi

  DOI：10.1081/scc-100106034

  日期：2001.1

  2,4-Disubstituted nortropinone derivatives 2, with anticipated anticonvulsant activity, were synthesized by the reaction of N-substituted nortropinones, ethanol, 5N-NaOH, and aromatic aldehydes (R1CHO).
• The cytotoxic properties and preferential toxicity to tumour cells displayed by some 2,4-bis(benzylidene)-8-methyl-8-azabicyclo[3.2.1] octan-3-ones and 3,5-bis(benzylidene)-1-methyl-4-piperidones
  作者：Hari N. Pati、Umashankar Das、Swagatika Das、Brian Bandy、Erik De Clercq、Jan Balzarini、Masami Kawase、Hiroshi Sakagami、J. Wilson Quail、James P. Stables、Jonathan R. Dimmock

  DOI：10.1016/j.ejmech.2008.03.015

  日期：2009.1

  This study demonstrated that replacement of the axial protons on the C2 and C6 atoms of various 1-methyl-3,5-bis(benzylidene)-4-piperidones 3 by a dimethylene bridge leading to series 2 lowered cytotoxic potencies. Four compounds 2a and 3a-c emerged as lead molecules based on their toxicity towards different neoplasms and their selective toxicity for malignant rather than normal cells. Some possible reasons for the disparity between the IC50 values in the two series of compounds are presented based on molecular modeling, log P values and respiration in rat liver mitochondria. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Willstaetter, Chemische Berichte, 1897, vol. 30, p. 731,2681,2716
  作者：Willstaetter

  DOI：——

  日期：——
• Two isomers of 2,4-dibenzyl-8-azabicyclo[3.2.1]octan-3-ol
  作者：Guangrong Zheng、Sean Parkin、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1107/s0108270103026520

  日期：2004.1.15

  The crystal structures of the title compounds, 2alpha,4alpha-dibenzyl-3alpha-tropanol (2alpha,4alpha-dibenzyl-8-methyl-8-azabicyclo[3.2.1]octan-3alpha-ol), C22H27NO, (I), and 2alpha,4alpha-dibenzyl-3beta-tropanol (2alpha,4alpha-dibenzyl-8-methyl-8-azabicyclo[3.2.1]octan-3beta-ol), C22H27NO, (II), show that both compounds have a piperidine ring in a chair conformation and a pyrrolidine ring in an envelope conformation. Isomer (I) is asymmetric, the benzyl groups having different orientations, whereas isomer (II) is mirror symmetric, and the N and O atoms, the C atom attached to the hydroxy group, and the methyl C atom attached to the N atom lie on the mirror plane. In the crystal structures of both (I) and (II), the molecules are linked together by intermolecular O-H...N hydrogen bonds to form chains that run parallel to the a direction in (I) and parallel to b in (II).