1-(1-phenylsulfanylvinyl)cyclopentanol | 141928-32-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(1-phenylsulfanylvinyl)cyclopentanol
• 英文别名: 1-(1-Phenylsulfanylethenyl)cyclopentan-1-ol
• CAS: 141928-32-7
• 化学式: C₁₃H₁₆OS
• 分子量: 220.335
• InChiKey: GEVFMQXLMCPKCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1-phenylsulfanylvinyl)cyclopentanol 在 过氧化双月桂酰 、 sodium hydride 作用下， 以 二甲基亚砜 、 乙酸乙酯 、 mineral oil 为溶剂， 反应 0.33h， 生成 5-cyclopentylidene-5-(phenylthio)pentan-2-one
  参考文献：
  名称：

  通过自由基烯丙基化的三取代和四取代官能化乙烯基硫化物

  摘要：

  衍生自苯基乙烯基硫化物的2-氟吡啶基-6-氧基-前体与黄原酸酯生成的自由基通过加成-消除过程反应，从而以高收率提供了相应的乙烯基硫化物。这种会聚方法操作简单，可直接合成难以获得的四取代乙烯基硫化物。乙烯基硫化物在与N-酰基阳离子发生高度立体选择性的反应中，被用作更坚固的烯醇醚替代物，从而导致含氮多环结构。

  DOI：

  10.1021/ol403103u
• 作为产物：
  描述：

  1-乙炔基环戊醇 、 苯硫酚 在 palladium diacetate 作用下， 以 硝基甲烷 为溶剂， 反应 0.25h， 生成 1-(1-phenylsulfanylvinyl)cyclopentanol
  参考文献：
  名称：

  One-Pot Synthesis of Keto Thioethers by Palladium/Gold-Catalyzed Click and Pinacol Reactions

  摘要：

  An atom-efficient synthesis of keto thioethers was devised via tandem gold/palladium catalysis. The reaction proceeds through a regioselective thiol attack at the beta-position of the alcohol, followed by an alkyl, aryl, or benzyl 1,2-shift. Both acyclic and cyclic systems were studied, in the latter case leading to the ring expansion of cyclic substrates.

  DOI：

  10.1021/ol502553p

文献信息

• Polylithiation of thioethers: a versatile route for polyanionic synthons
  作者：Miguel Yus、Ana Gutiérrez、Francisco Foubelo

  DOI：10.1016/s0040-4020(01)00374-x

  日期：2001.5

  hydroxy thioether 2. The same methodology was applied to the cyclopropyl phenyl thioether (4), cyclopropyl 1,3-diols 5 E1=tBuCHO, PhCHO, [Me(CH2)4]2CO, (CH2)5CO, (CH2)7CO; E2=tBuCHO, Me2CO, (CH2)5CO} being isolated in moderate yields. The successive treatment of bis(phenylthio)methane (7) with: (a) n-butyllithium at 0°C, (b) a carbonyl compound [E1=tBuCHO, Me2CO, Et2CO, (CH2)5CO] at −40°C, (c) lithium

  苯基乙烯基硫醚（1）与正丁基锂和亲电子体[E 1 = PhCHO，（CH 2）4 CO，（CH 2）5 CO]在-78°C的THF中连续反应，水解后得到预期的亚甲基羟基硫醚（2）。用正丁基锂对2进行质子化，然后进行DTBB催化的锂化反应，并与第二种亲电试剂[E 2 = t BuCHO，PhCHO，Me 2 CO，（CH 2）5 CO]反应，在-78°C下水解相应的亚甲基二醇3。可以从一锅法中从1开始制备相同的二醇，而无需分离羟基硫醚2。将相同的方法应用于环丙基苯基硫醚（4），环丙基1,3-二醇5 E 1 = t BuCHO，PhCHO，[Me（CH 2）4 ] 2 CO，（CH 2）5 CO，（CH 2）7一氧化碳；E 2 = t BuCHO，Me 2 CO，（CH 2）5 CO}以中等收率分离。双（苯硫基）甲烷的连续处理（7）：（a）在0°C时的正丁基锂，（b）在-40°C时的羰基化合物[E
• The first example of transition-metal-catalyzed addition of aromatic thiols to acetylenes
  作者：Hitoshi Kuniyasu、Akiya Ogawa、Kenichiro Sato、Ilhyong Ryu、Nobuaki Kambe、Noboru Sonoda

  DOI：10.1021/ja00040a087

  日期：1992.7
• Phenyl vinyl thioether: A convenient source of the ethylene 1,1-dianion
  作者：Francisco Foubelo、Ana Gutiérrez、Miguel Yus

  DOI：10.1016/s0040-4039(99)01731-1

  日期：1999.11

  The successive reaction of phenyl vinyl thioether (1) with n-butyllithium and an etectrophile [E-1= PhCHO, (CH2)(4)CO, (CH2)(5)CO] in THF at -78 degrees C gives, after hydrolysis, the expected methylenic hydroxy thioethers (2). Deprotonation of 2 with n-butyllithium followed by a DTBB-catalysed lithiation and reaction with a second electrophile [E2= (BuCHO)-Bu-t, PbCHO, Me2CO. (CH2)(5)CO], also at -78 C, gives after hydrolysis the corresponding methylenic 1,3-diols 3. When carbon dioxide is used as the second electrophile, the expected methylenic hydroxy acid 3cd is isolated. The whole process can be performed in a one-pot manner without isolation of the intermediates 2. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Tri- and Tetrasubstituted Functionalized Vinyl Sulfides by Radical Allylation
  作者：Laurent Debien、Marie-Gabrielle Braun、Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1021/ol403103u

  日期：2013.12.20

  2-Fluoropyridinyl-6-oxy- precursors derived from phenyl vinyl sulfide react with radicals generated from xanthates via an addition–elimination process to furnish the corresponding vinyl sulfides in good yields. This convergent method is operationally simple and enables a straightforward synthesis of the difficult to access tetrasubstituted vinyl sulfides. Vinyl sulfides were used as more robust enol ether surrogates

  衍生自苯基乙烯基硫化物的2-氟吡啶基-6-氧基-前体与黄原酸酯生成的自由基通过加成-消除过程反应，从而以高收率提供了相应的乙烯基硫化物。这种会聚方法操作简单，可直接合成难以获得的四取代乙烯基硫化物。乙烯基硫化物在与N-酰基阳离子发生高度立体选择性的反应中，被用作更坚固的烯醇醚替代物，从而导致含氮多环结构。
• One-Pot Synthesis of Keto Thioethers by Palladium/Gold-Catalyzed Click and Pinacol Reactions
  作者：Alban Cadu、Rahul A. Watile、Srijit Biswas、Andreas Orthaber、Per J. R. Sjöberg、Joseph S. M. Samec

  DOI：10.1021/ol502553p

  日期：2014.11.7

  An atom-efficient synthesis of keto thioethers was devised via tandem gold/palladium catalysis. The reaction proceeds through a regioselective thiol attack at the beta-position of the alcohol, followed by an alkyl, aryl, or benzyl 1,2-shift. Both acyclic and cyclic systems were studied, in the latter case leading to the ring expansion of cyclic substrates.

表征谱图