6-ethenyl-2,2,6-trimethyl-3-(phenylseleno)tetrahydropyran | 70188-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 6-ethenyl-2,2,6-trimethyl-3-(phenylseleno)tetrahydropyran
• 英文别名: 2H-Pyran, 6-ethenyltetrahydro-2,2,6-trimethyl-3-(phenylseleno)-；6-ethenyl-2,2,6-trimethyl-3-phenylselanyloxane
• CAS: 70188-06-6
• 化学式: C₁₆H₂₂OSe
• 分子量: 309.31
• InChiKey: NUTNBJRMHUZUCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  6-ethenyl-2,2,6-trimethyl-3-(phenylseleno)tetrahydropyran 在 sodium hydroxide 、 硼烷 、 双氧水 作用下， 生成 2-(2,6,6-Trimethyl-3,6-dihydro-2H-pyran-2-yl)-ethanol
  参考文献：
  名称：

  The use of acyclic monoterpenes in the preparation of β-pyrones: Synthesis of the right-hand fragment of Usneoidone E

  摘要：

  The right hand fragment, 36, of Usneoidone E, 1, a powerful antiviral and antitumoural agent has been synthesized from the beta-pyrone 32. Using linalool as starting material, a 2,2,6,6-tetrasubstituted dihydropyrane 20, precursor of 32 and 33, was prepared. 20 was also synthesized From geranyl acetate through selenide 7, and is a versatile precursor for the synthesis of tetaprenyltoluquinols. Unambiguous C-13 NMR assignment has been done by 2D correlations.

  DOI：

  10.1016/0040-4020(95)00084-l
• 作为产物：
  描述：

  2-Phenylselanyl-2-(2,6,6-trimethyl-5-phenylselanyl-tetrahydro-pyran-2-yl)-ethanol 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以81%的产率得到6-ethenyl-2,2,6-trimethyl-3-(phenylseleno)tetrahydropyran
  参考文献：
  名称：

  The use of acyclic monoterpenes in the preparation of β-pyrones: Synthesis of the right-hand fragment of Usneoidone E

  摘要：

  The right hand fragment, 36, of Usneoidone E, 1, a powerful antiviral and antitumoural agent has been synthesized from the beta-pyrone 32. Using linalool as starting material, a 2,2,6,6-tetrasubstituted dihydropyrane 20, precursor of 32 and 33, was prepared. 20 was also synthesized From geranyl acetate through selenide 7, and is a versatile precursor for the synthesis of tetaprenyltoluquinols. Unambiguous C-13 NMR assignment has been done by 2D correlations.

  DOI：

  10.1016/0040-4020(95)00084-l

文献信息

• Pyridine-facilitated phenylselenoetherification of some tertiary alkenols
  作者：Biljana M. Mojsilovic、Zorica M. Bugaric

  DOI：10.1002/hc.1072

  日期：——

  An improved procedure for intramolecular cyclization of tertiary alkenols using benzeneselenyl halides has been developed. We found that cyclization can be facilitated by pyridine. Thus, in the presence of an equimolar amount of pyridine, a chemospecific reaction could be observed that resulted in formation of corresponding cyclic ethers, and quantitative yields were achieved instantaneously under

  已经开发了一种使用苯硒基卤化物进行叔烯醇分子内环化的改进方法。我们发现吡啶可以促进环化。因此，在等摩尔量的吡啶存在下，可以观察到导致形成相应环醚的化学特异性反应，并且在极其温和的实验条件下立即实现定量收率。硒化试剂的卤化物离子的影响不显着，两种卤化物通常给出相同的结果 © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:475–479, 2001
• Phenylselenoetherification of some Δ4-alkenols facilitated by pyridine and some Lewis acids
  作者：Biljana M. Šmit、Zorica M. Bugarčić

  DOI：10.1002/jhet.487

  日期：2010.11

  Studies on the phenylselenoetherification of some Δ4‐alkenols in the presence of pyridine and some Lewis acids are described. All alkenols underwent intramolecular cyclization yielding corresponding tetrahydrofuran or tetrahydropyran derivatives. Yield and diastereomeric ratio of the cyclic products depend on counterion of selenylating reagent used. We found that external additives, such as pyridine

  研究一些Δ的phenylselenoetherification 4个在吡啶存在-alkenols和一些路易斯酸说明。所有烯醇都进行分子内环化，得到相应的四氢呋喃或四氢吡喃衍生物。环状产物的产率和非对映异构体比例取决于所用硒化试剂的抗衡离子。我们发现，外部添加剂，例如吡啶和一些与亲电子和/或亲核物质配位的路易斯酸，可用于高效控制环化过程并提高立体诱导水平。J.杂环化​​学。（2010）。
• Cyclization of some terpenic alcohols by phenylselenoetherification reaction
  作者：Marina D. Rvović、Vera M. Divac、Nenad Ž. Janković、Zorica M. Bugarčić

  DOI：10.1007/s00706-013-1006-7

  日期：2013.8

  AbstractHighly substituted tetrahydrofuran (THF)- and tetrahydropyran (THP)-type rings are formed through an acid- or base-catalyzed 5-exo and/or 6-endo cyclization of some natural terpenic alcohols (e.g., linalool, nerolidol, and α-terpineol) by an electrophile-mediated cyclization with PhSeCl and PhSeBr. The side chains of these cyclic ether products can be further transformed easily into a wide

  摘要高度取代的四氢呋喃（THF） -和四氢吡喃（THP）型环通过酸-或碱-催化的5-形成外和/或6-内一些天然萜醇（环化例如，里哪醇，橙花叔醇，和α-萜品醇）通过亲电试剂与PhSeCl和PhSeBr介导的环化反应。由于双键的多功能性，这些环状醚产物的侧链可以轻松地进一步转化为多种底物。在这些反应中注意到某些区域选择性。Nerolidol在与PhSeX反应中表现得像芳樟醇，主要提供THF衍生物，而α-松油醇提供THP。一些路易斯碱（三乙胺，吡啶，2,2'-联吡啶和喹啉）和路易斯酸（SnCl 2和CoCl2）被用作添加剂，添加剂的存在可使收率从5–40％提高到几乎定量。 图形概要
• Konstantinovic, S.; Bugarcic, Z.; Marjanovic, Lj., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 11, p. 1169 - 1170
  作者：Konstantinovic, S.、Bugarcic, Z.、Marjanovic, Lj.、Gojkovic, S.、Mihailovic, M. Lj.

  DOI：——

  日期：——
• Cyclization of terpene alcohols and related polyenols by benzeneselenenyl triflate
  作者：Shizuaki Murata、Toshiyasu Suzuki

  DOI：10.1016/s0040-4039(00)97110-7

  日期：1990.1