2-methylene-4-phenylpent-4-enyl 3-(1-naphthyl)prop-2-ynyl ether | 1015098-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methylene-4-phenylpent-4-enyl 3-(1-naphthyl)prop-2-ynyl ether
• 英文别名: 1-[3-(2-Methylidene-4-phenylpent-4-enoxy)prop-1-ynyl]naphthalene；1-[3-(2-methylidene-4-phenylpent-4-enoxy)prop-1-ynyl]naphthalene
• CAS: 1015098-70-0
• 化学式: C₂₅H₂₂O
• 分子量: 338.449
• InChiKey: TUXSTAVYSHARDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methylene-4-phenylpent-4-enyl 3-(1-naphthyl)prop-2-ynyl ether 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 [2'-(diphenylphosphanyl)-[1,1'-binaphthalen]-2-yl]diphenylphosphane 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 (Z)-4-(1-naphthylmethylene)-7-phenyl-2-oxaspiro[4.4]non-6-ene 、 (Z)-4-(1-naphthylmethylene)-7-phenyl-2-oxaspiro[4.4]non-6-ene
  参考文献：
  名称：

  Enantioselective Syntheses of Various Chiral Multicyclic Compounds with Quaternary Carbon Stereocenters by Catalytic Intramolecular Cycloaddition

  摘要：

  The intramolecular cycloaddition of 1,n-diene-ynes (n = 4-6), where alkyne and alkene moieties are connected by a 1,1-disubstituted alkene, was examined using a chiral rhodium catalyst, and various types of cycloadducts with quaternary carbon stereocenter(s) were obtained in high to excellent enantiomeric excess. In the case of 1,4-diene-ynes, tricyclic, bicyclic, and spirocyclic compounds were obtained depending upon the substituents at the 2-position of the 1,4-diene moiety and those at their alkyne termini. On the other hand, 1,5- and 1,6-diene-ynes gave tricyclic and bicyclic compounds, which included medium-sized ring systems. The mechanistic considerations for different reaction pathways and the synthetic transformation of tricyclic products into functionalized spirocyclic compounds are also described. The reaction of enediynes, where two alkyne moieties are connected by a 1,1-disubstituted alkene, was also examined, and sterically strained tricyclic compounds with two carbon stereocenters were obtained.

  DOI：

  10.1021/ja0762083
• 作为产物：
  描述：

  2-methylene-4-phenylpent-4-en-1-ol 、 1-(3-溴-1-丙炔基)萘 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-methylene-4-phenylpent-4-enyl 3-(1-naphthyl)prop-2-ynyl ether
  参考文献：
  名称：

  Enantioselective Syntheses of Various Chiral Multicyclic Compounds with Quaternary Carbon Stereocenters by Catalytic Intramolecular Cycloaddition

  摘要：

  The intramolecular cycloaddition of 1,n-diene-ynes (n = 4-6), where alkyne and alkene moieties are connected by a 1,1-disubstituted alkene, was examined using a chiral rhodium catalyst, and various types of cycloadducts with quaternary carbon stereocenter(s) were obtained in high to excellent enantiomeric excess. In the case of 1,4-diene-ynes, tricyclic, bicyclic, and spirocyclic compounds were obtained depending upon the substituents at the 2-position of the 1,4-diene moiety and those at their alkyne termini. On the other hand, 1,5- and 1,6-diene-ynes gave tricyclic and bicyclic compounds, which included medium-sized ring systems. The mechanistic considerations for different reaction pathways and the synthetic transformation of tricyclic products into functionalized spirocyclic compounds are also described. The reaction of enediynes, where two alkyne moieties are connected by a 1,1-disubstituted alkene, was also examined, and sterically strained tricyclic compounds with two carbon stereocenters were obtained.

  DOI：

  10.1021/ja0762083

文献信息

• Enantioselective Syntheses of Various Chiral Multicyclic Compounds with Quaternary Carbon Stereocenters by Catalytic Intramolecular Cycloaddition
  作者：Takanori Shibata、Yu-ki Tahara、Kohei Tamura、Kohei Endo

  DOI：10.1021/ja0762083

  日期：2008.3.1

  The intramolecular cycloaddition of 1,n-diene-ynes (n = 4-6), where alkyne and alkene moieties are connected by a 1,1-disubstituted alkene, was examined using a chiral rhodium catalyst, and various types of cycloadducts with quaternary carbon stereocenter(s) were obtained in high to excellent enantiomeric excess. In the case of 1,4-diene-ynes, tricyclic, bicyclic, and spirocyclic compounds were obtained depending upon the substituents at the 2-position of the 1,4-diene moiety and those at their alkyne termini. On the other hand, 1,5- and 1,6-diene-ynes gave tricyclic and bicyclic compounds, which included medium-sized ring systems. The mechanistic considerations for different reaction pathways and the synthetic transformation of tricyclic products into functionalized spirocyclic compounds are also described. The reaction of enediynes, where two alkyne moieties are connected by a 1,1-disubstituted alkene, was also examined, and sterically strained tricyclic compounds with two carbon stereocenters were obtained.