顺式-3,4-二氢-3-(苯基甲基)-2H-1-苯并吡喃-4-醇 | 60206-81-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 中文名称: 顺式-3,4-二氢-3-(苯基甲基)-2H-1-苯并吡喃-4-醇
• 英文名称: (+/-)-(3R,4S)-3-benzylchroman-4-ol
• 英文别名: (trans)-3-benzylchroman-4-ol；3alpha-Benzylchroman-4beta-ol；(3S,4R)-3-benzyl-3,4-dihydro-2H-chromen-4-ol
• CAS: 60206-81-7；60206-82-8；129056-63-9；129056-64-0
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: PXYMHFRDMNPYMI-XJKSGUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  顺式-3,4-二氢-3-(苯基甲基)-2H-1-苯并吡喃-4-醇 在 jones' reagent 作用下， 以210 mg的产率得到3-benzyl-4-chromanone
  参考文献：
  名称：

  Chatterjee, Amareshwar; Dutta, Lakshmi N.; Chatterjee, Swapan K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 11, p. 955 - 960

  摘要：

  DOI：
• 作为产物：
  描述：

  3-benzylidene-chroman-4-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 顺式-3,4-二氢-3-(苯基甲基)-2H-1-苯并吡喃-4-醇
  参考文献：
  名称：

  Chatterjee, Amareshwar; Dutta, Lakshmi N.; Chatterjee, Swapan K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 11, p. 955 - 960

  摘要：

  DOI：

文献信息

• Tributyltin hydride-mediated radical cyclisation of aldehydes and unsaturated ketones: the synthesis of hydroxy tetrahydrofurans, chromanols and related compounds
  作者：David Bebbington、Jon Bentley、Paul A Nilsson、Andrew F Parsons

  DOI：10.1016/s0040-4039(00)01586-0

  日期：2000.11

  The tributyltin hydride-mediated cyclisation of unsaturated ethers bearing an aldehyde or α,β-unsaturated ketone group is reported. Cyclisation proceeds via addition of the tributyltin radical to the carbonyl double bond and the resultant O-stannyl ketyl can add intramolecularly to electron-rich double bonds to form hydroxy tetrahydrofurans, chromanols or related compounds.

  据报道，三丁基氢化锡介导的带有醛或α，β-不饱和酮基的不饱和醚的环化。环化反应是通过将三丁基锡自由基加到羰基双键上而进行的，所得的O-锡烷基缩酮可以分子内加至富电子双键上，形成羟基四氢呋喃，苯并二氢呋喃或相关化合物。
• Tributyltin hydride-mediated radical cyclisation of carbonyls to form functionalised oxygen and nitrogen heterocycles
  作者：Jon Bentley、Paul A. Nilsson、Andrew F. Parsons

  DOI：10.1039/b202077g

  日期：2002.6.7

  The tributyltin hydride-mediated cyclisation of unsaturated ethers and amines bearing an aldehyde or α,β-unsaturated ketone group is reported. Cyclisation proceeds via reversible addition of the tributyltin radical to the carbonyl double bond to form an intermediate O-stannyl ketyl. This nucleophilic radical can add intramolecularly to electron-rich double bonds to form substituted 5- or 6-membered

  三丁基氢化锡介导的不饱和环化反应 醚 和 胺类 轴承 醛 或α，β-不饱和 酮 组被报告。 环化前进经由可逆加成的三丁基锡的基团的羰双键形成中间体O-锡烷基缩酮。该亲核基团可以分子内加至富含电子的双键上，以形成取代的5或6元环。环化形成例如羟基四氢呋喃的效率，铬醇 或者 喹诺酮类所显示的R 1取决于受体双键的性质以及中间体O-锡烷基缩酮的稳定性。因此，首次显示出共振稳定的烯丙基或苄基的O-锡烷基酮基自由基在缓慢的自由基环化中具有特殊的应用，从而导致丁内酯或吡喃。
• Reductions par les hydrures et hydroboration etude de la stereoselectivite de nouvelles voies d'acces aux 3-arylmethyl-4-chromanols (Homoisoflavanols)
  作者：Michel Gomis、B. Serge Kirkiacharian

  DOI：10.1016/s0040-4020(01)89754-4

  日期：1990.1

  The reduction of 3-arylmethyl-4-chromanones by sodium borohydride, lithium tri-tert-butoxyaluminum hydride and hydroboration followed by oxydation of 3-benzyl-4-hydroxy-coumarines lead to mixtures of Cis and Trans diastereoisomers of 3-arylmethyl-4-chromanols (homoisoflavanols). The reduction of 3-arylmethyl-4-chroma- nones by diborane or bis-tert-butylthioethane diborane (BTED) is stereoselective

  通过硼氢化钠，三叔丁氧基铝氢化锂和氢硼化还原3-芳基-4-铬烷酮，然后氧化3-苄基-4-羟基香豆素，导致3-芳基甲基-4的顺式和反式非对映异构体的混合物-铬醇（纯黄烷醇）。乙硼烷或双叔丁基硫代乙二硼烷（BTED）还原3-芳基甲基-4-色氨酸是立体选择性的，并形成顺式和反式非对映异构体，收率很高；9-borabicyclo- [3.3.1。]-壬烷（9-BBN）的使用会降低这种立体选择性。
• Gomis, M.; Kirkiacharian, B.S.; Likforman, J., Bulletin de la Societe Chimique de France, 1988, # 3, p. 585 - 590
  作者：Gomis, M.、Kirkiacharian, B.S.、Likforman, J.、Mahuteau, J.

  DOI：——

  日期：——
• Synthesis and antirhinovirus activity of new 3-benzyl chromene and chroman derivatives
  作者：Cinzia Conti、Nicoletta Desideri

  DOI：10.1016/j.bmc.2009.03.051

  日期：2009.5

  A series of 3-benzyl chromenes and chromans were synthesized and tested in vitro against human rhinovirus (HRV) 1B and 14, two representative serotypes for rhinovirus group B and A, respectively. All the new compounds, with the exception of 3-benzyl-2H-chromene (3a), showed a potent activity against HRV serotype 1B within micro or submicromolar range (IC(50)s from 0.11 to 6.62 mu M). The low cytotoxicity of all the derivatives resulted in compounds with high therapeutic index (TI). On the contrary, HRV 14 infection was only weakly inhibited by the majority of these compounds. The 3-benzylidenechromans 2b and 2c showed the highest anti-HRV 1B activity (IC50 0.12 and 0.11 mu M, respectively) coupled with remarkable TI (625.00 and 340.91, respectively). Mechanism of action studies on (Z)-3-(4-chlorobenzylidene) chroman (2b) suggest that the new compounds behave as capsid binders and interfere with very early stages of HRV 1B replication, similarly to related flavanoids. (C) 2009 Elsevier Ltd. All rights reserved.