5-phenylthiopent-3-yn-2-ol | 122663-76-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-phenylthiopent-3-yn-2-ol
• 英文别名: 3-Pentyn-2-ol, 5-(phenylthio)-；5-phenylsulfanylpent-3-yn-2-ol
• CAS: 122663-76-7
• 化学式: C₁₁H₁₂OS
• 分子量: 192.282
• InChiKey: FNBJCZVFDRJDFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  5-phenylthiopent-3-yn-2-ol 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以71%的产率得到5-Phenylsulfanyl-penta-3,4-dien-2-ol
  参考文献：
  名称：

  Convenient method for the preparation of 1-phenylthio-3-alken-1-ynes and 4-hydroxy-1-phenylthio-1,2-alkadienes from a common precursor

  摘要：

  4-Hydroxy-1-phenylthio-2-alkynes (5) reacted with dihydropyran to afford the corresponding 4-tetrahydropyranyloxy derivatives which, on treatment with KHMDS, gave a mixture of (E)- and (Z)-1-phenylthio-3-alken-1-ynes, with the former predominant. When MeLi was used in the place of KHMDS, the (Z)-isomers were formed in preference to the (E)-isomers. Further treatment of the mixture with a base converted the (Z)-isomers into (E)-isomers. On the other hand, the reaction of 5 with KHMDS gave the corresponding 4-hydroxy-1-phenythio-1,2-alkadienes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01380-1
• 作为产物：
  描述：

  苯硫酚 在 sodium hydroxide 、 乙基溴化镁 、 四丁基氟化铵 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 5-phenylthiopent-3-yn-2-ol
  参考文献：
  名称：

  八元和九元环状烯丙基ulf化萘的σ重排中的立体选择性。乙烯基取代的丁内酯和戊内酯的合成

  摘要：

  （）-4-苯甲硫基-2-丁烯-1-醇衍生物6的铑（II）乙酸铑催化的[2,3]σ-重排重氮丙二酸酯提供了高度立体选择性的乙烯基取代的丁内酯10以这种方式，虽然重排同系物的重氮丙二酸酯，但（）-5-苯硫基-3-戊烯-1-醇衍生物9产生了乙烯基取代的戊内酯13和14，前者占优势。发现使用9中的立体化学固定的取代基R是导致后面的重排中的高立体选择性的重要因素，如通过使用重氮丙二酸酯20b作为底物所显示的。

  DOI：

  10.1016/s0040-4020(01)85601-5

文献信息

• A Highly Regioselective Reaction of Allylic Acetates with Silylated Carbon Nucleophiles Directed by a Sulfenyl Group. Scope, Limitation, and Mechanistic Aspects
  作者：Kazuaki Kudo、Yukihiko Hashimoto、Hitoshi Houchigai、Masaki Hasegawa、Kazuhiko Saigo

  DOI：10.1246/bcsj.66.848

  日期：1993.3

  α-(Sulfenylmethyl)allyl acetates reacted with silylated carbon nucleophiles in the presence of a catalytic amount of TMSOTf to give products substituted at the α-position of the sulfenylmethyl group in moderate to good yields with high regioselectivity. The theoretical calculation on an intermediate cationic species indicated that an episulfonium ion was a stable form; the observed regioselectivity was rationalized qualitatively on the basis of the coefficients of LUMO of the cation. Some transformations of the products were also demonstrated.

  α-(Sulfenyl甲基)烯丙基醋酸盐在催化量的TMSOTf存在下，与硅烷化的碳亲核试剂反应，以中等至良好的产率和高度区域选择性在硫代甲基的α-位置上进行取代。对中间体阳离子物种的理论计算表明，环硫鎓离子是一种稳定形式；观察到的区域选择性定性地基于阳离子的LUMO系数进行合理化。还展示了一些产物的转化。
• Stereoselectivity in the sigmatropic rearrangement of eight- and nine-membered cyclic allylsulfonium ylides. synthesis of vinyl- substituted butyro- and valerolactones
  作者：Fusao Kido、Subhash C. Sinha、Toshiya Abiko、Masataka Watanabe、Akira Yoshikoshi

  DOI：10.1016/s0040-4020(01)85601-5

  日期：1990.1

  The rhodium (II) acetate-catalyzed [2,3]sigma-tropic rearrangement of the diazo malonates of ()-4-phen-ylthio-2-buten-l-ol derivatives 6 afforded vinyl-substituted butyrolactones 10 in a highly stereoselective manner, while the rearrangement of the diazo malonates of homologues, ()-5-phenylthio-3-penten-1-ol derivatives 9, yielded vinyl-substituted valerolactones 13 and 14 in the predominance of the

  （）-4-苯甲硫基-2-丁烯-1-醇衍生物6的铑（II）乙酸铑催化的[2,3]σ-重排重氮丙二酸酯提供了高度立体选择性的乙烯基取代的丁内酯10以这种方式，虽然重排同系物的重氮丙二酸酯，但（）-5-苯硫基-3-戊烯-1-醇衍生物9产生了乙烯基取代的戊内酯13和14，前者占优势。发现使用9中的立体化学固定的取代基R是导致后面的重排中的高立体选择性的重要因素，如通过使用重氮丙二酸酯20b作为底物所显示的。
• Stereoselective synthesis of contiguously substituted butyrolactones based on the cyclic allylsulfonium ylide rearrangement
  作者：Fusao Kido、Subhash C. Sinha、Toshiya Abiko、Akira Yoshikoshi

  DOI：10.1016/s0040-4039(00)99523-6

  日期：1989.1

  α-Diazomalonates of ()-4-phenylthio-2-buten-1-ol homologues (2) stereoselectively provided γ-alkyl-α-ethoxycarbonyl-α-phenylthio-β-vinylbutyrolactones (1) by the [2.3]sigmatropic rearrangement of cyclic sulfonium ylides (3) intramolecularly generated therefrom with rhodium acetate.

  （）-4-苯硫基-2-丁烯-1-醇同系物（2）的α-重氮丙二酸酯通过[2.3]σ的重排重排选择性立体地提供了γ-烷基-α-乙氧基羰基-α-苯硫基-β-乙烯基丁内酯（1）。用乙酸铑从其分子内产生的环状磺酸盐（3）。
• KIDO, FUSAO;SINHA, SUBHASH C.;ABIKO, TOSHIYA;YOSHIKOSHI, AKIRA, TETRAHEDRON LETT., 30,(1989) N2, C. 1575-1578
  作者：KIDO, FUSAO、SINHA, SUBHASH C.、ABIKO, TOSHIYA、YOSHIKOSHI, AKIRA

  DOI：——

  日期：——
• Stereoselective Synthesis of (Z)-a-Phenoxymethylene-g-butyrolactone and Its Sulfur Analogues from 2-Propynyloxy- or 2-Propynylthiobenzene
  作者：Fen-Tair Luo、Sheng-Li Ko、Lijun Liu、Hui Chen

  DOI：10.3987/com-00-8964

  日期：——

  The preparations of (Z)-alpha -phenoxymethylene-gamma -butyrolactone, alpha -phenoxymethyl-gamma -butyrolactone, (Z)-alpha -phenylthiomethylene-gamma -butyrolactone, and alpha -phenylthiomethyl-gamma -butyrolactone derivatives from 2-propynyloxy-benzene and 2-propynylthiobenzene were described.