(E)-1-methoxy-3-(phenylthio)propene | 81850-14-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (E)-1-methoxy-3-(phenylthio)propene
• 英文别名: (E)-1-methoxy-3-phenylthiopropene；[[(E)-3-methoxyprop-2-enyl]thio]benzene；[(E)-3-methoxyprop-2-enyl]sulfanylbenzene
• CAS: 81850-14-8
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: SPUCQQSCSUCEMG-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙炔醛 、 (E)-1-methoxy-3-(phenylthio)propene 生成 (3R,4S)-4-Methoxy-hex-5-en-1-yn-3-ol
  参考文献：
  名称：

  Reactions of Cobalt-Complexed Acetylenic Aldehydes with Chiral (γ-Alkoxyallyl)boranes:  Enantioselective Synthesis of 3,4-Dioxy 1,5-Enynes and Stereoselective Entry to Polyfunctional Building Blocks

  摘要：

  Toward the goal of developing enantioselective routes to polyfunctional building blocks using Co-based technology, the reactions of(Z)- and (E)-(gamma-alkoxyallyl)diisopinocampheylboranes (8, 13) with acetylenic aldehydes and their -Co-2(CO)(6) complexes (10a-c) have been investigated. Whereas phenylpropynal reacts with (Z)-8 with poor efficiency (<10% yield) and moderate enantioselectivity, the corresponding Co derivatives 10 undergo high-yielding (65-76%), diastereoselective (88->95% de), and enantioselective (>96% ee) reactions, producing syn-(3,4-dioxy 1,5-enyne)Co-2(CO)(6) 11a-f. Similarly, the newly prepared (E)-boranes 13 also react efficienctly with the complexed aldehydes, affording the corresponding (anti-3,4-dioxy 1,5-enyne)Co-2(CO)(6) complexes 15a-c with virtually complete diastereo- and enantioselectivity, while phenylpropynal itself reacts inefficiently and with lower enantioselectivity. Oxidative demetalation of the complexed adducts affords the 3,4-dioxy 1,5-enynes 17 with complete maintenance of stereochemical integrity. Osmium-catalyzed dihydroxylation of a representative dioxy enyne, i.e., 17c, proceeds with high diastereoselectively (9:1), favoring addition anti to the allylic alkoxy group. Although epoxidation of enynediol 25 by t-BuOOH/VO(acac)(2) occurs stereoselectively, it is accompanied by epimerization of the diol unit.

  DOI：

  10.1021/jo9619387
• 作为产物：
  描述：

  3-(phenylthio)-3-methoxypropene 在 三氟甲磺酸 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以71%的产率得到(E)-1-methoxy-3-(phenylthio)propene
  参考文献：
  名称：

  Heteroatom-directed allylic substitution and rearrangement reactions

  摘要：

  DOI：

  10.1021/jo00381a014

文献信息

• Thiostannane-mediated preparation of γ-alkoxyallyl sulfides; efficient β-alkylation of α,β-unsaturated aldehydes
  作者：Tsuneo Sato、Hiroshi Okazaki、Junzo Otera∗、Hitosi Nozaki

  DOI：10.1016/0040-4039(88)85063-9

  日期：1988.1

  The title β-alkylation is achieved through a sequence of sulfenylation of α-enal acetals, -BuLi-promoted alkylation, and oxidative hydrolysis.

  标题β-烷基化是通过一系列α-烯醇缩醛的亚磺酰基化，-BuLi促进的烷基化和氧化水解来实现的。
• Hoffmann, Reinhard W.; Kemper, Bruno; Metternich, Rainer, Liebigs Annalen der Chemie, 1985, # 11, p. 2246 - 2260
  作者：Hoffmann, Reinhard W.、Kemper, Bruno、Metternich, Rainer、Lehmeier, Thomas

  DOI：——

  日期：——
• SATO, TSUNEO;OTERA, JUNZO;NOZAKI, HITOSI, TETRAHEDRON, 45,(1989) N, C. 1209-1218
  作者：SATO, TSUNEO、OTERA, JUNZO、NOZAKI, HITOSI

  DOI：——

  日期：——
• TIETZE, LUTZ F.;LOGERS, MICHAEL, LIEBIGS ANN. CHEM.,(1990) N, C. 261-265
  作者：TIETZE, LUTZ F.、LOGERS, MICHAEL

  DOI：——

  日期：——
• HOFFMANN, R. W.;KEMPER, B., TETRAHEDRON LETT., 1981, 22, N 52, 5263-5266
  作者：HOFFMANN, R. W.、KEMPER, B.

  DOI：——

  日期：——