(1S,7S)-(2-phenylsulfonyl)-8-oxabicyclo[5.1.0]oct-2-ene | 474094-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,7S)-(2-phenylsulfonyl)-8-oxabicyclo[5.1.0]oct-2-ene
• 英文别名: (1S,7S)-2-(benzenesulfonyl)-8-oxabicyclo[5.1.0]oct-2-ene
• CAS: 474094-59-2
• 化学式: C₁₃H₁₄O₃S
• 分子量: 250.318
• InChiKey: XCSYOXSQTQNAQZ-AAEUAGOBSA-N

物化性质

• 沸点：
  447.6±45.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,7S)-(2-phenylsulfonyl)-8-oxabicyclo[5.1.0]oct-2-ene 在 咪唑 、 三甲基铝 、 sodium hexamethyldisilazane 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 C₂₀H₃₀OSSi
  参考文献：
  名称：

  [EN] LARGE-SCALE DIASTEREOSELECTIVE SYNTHESES OF CYCLOHEPTADIENYLSULFONES AND STEREOTETRADS
  [FR] SYNTHESES DIASTEREOSELECTIVES A GRANDE ECHELLE DE CYCLOHEPTADIENYLSULFONES ET DE STEREOTETRADES

  摘要：

  这项发明涉及大规模立体选择性合成环庚二烯基砜和立体四聚体的过程，这些是制备阿普利罗宁A的关键中间体。

  公开号：

  WO2016057606A1
• 作为产物：
  描述：

  1-(phenylthio)cycloheptene 在 (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III) 、 苯膦酸 、 双氧水 三乙烯二胺 、 sodium tungstate 、 磷酸 、 ammonium acetate 、 双氧水 、 sodium bromide 作用下， 以 甲醇 、 水 为溶剂， 反应 67.0h， 生成 (1S,7S)-(2-phenylsulfonyl)-8-oxabicyclo[5.1.0]oct-2-ene
  参考文献：
  名称：

  Improved and Environmentally Friendly Large-Scale Preparation of Cyclohexadienyl-, Cycloheptadienyl Sulfone and Enantiopure Epoxy Cycloheptyl Sulfones

  摘要：

  通过5个阶段的一次操作，制备了公斤级的环庚二烯基苯砜和环己二烯基苯砜，收率超过50%，无需纯化。本文描述了一种实用且高效的1,3-环庚二烯基砜的雅克布森不对称环氧化方法。该方法适用于大规模合成，无需使用卤代溶剂，也不需要色谱分析。

  DOI：

  10.1055/s-2004-822318

文献信息

• SN2′ addition/1,2-elimination of dimethylsulfonium methylide with epoxy vinyl sulfones: synthesis of exocyclic cross-conjugated dienyl sulfones
  作者：Vikas Sikervar、Philip L. Fuchs

  DOI：10.1039/c0cc05405d

  日期：——

  Dimethylsulfonium methylide undergoes S(N)2' addition/1,2-elimination with epoxy vinyl sulfones to generate enantiopure six and seven membered cross-conjugated hydroxy vinyl sulfones. Moderate to excellent yields were obtained for both six and seven membered substrates.

  二甲基s亚甲基与环氧乙烯基砜进行S（N）2'加成/ 1,2-消除，生成对映体纯的六元和七元交叉共轭羟基乙烯基砜。对于六元和七元基板，均获得了中等至极好的产量。
• Reagent-Directed Allylic Quadraselection. Chemoselective <i>Anti</i>- and <i>Syn</i>-Lawton S_N2′ Methylation of Seven-Membered Epoxyvinylsulfones
  作者：Wan Pyo Hong、Ahmad El-Awa、Philip L. Fuchs

  DOI：10.1021/ja9017557

  日期：2009.7.8

  Methods have been developed for regio- and stereoselective 1,4-syn or 1,4-anti methylation of seven-membered epoxyvinylsulfones. 1,4-Syn addition is achieved via the combination of Me2Zn and catalytic Li2CuCl4, a hitherto unexplored reagent combination. The complementary 1,4-anti addition relies on Cu(I) catalyzed methyl Grignard addition or (CH3)(3)Al assisted CH3Cu addition. The methods described were assayed on four diastereomeric stereodiads and on their parent epoxide.
• Syntheses of Highly Substituted Enantiopure C6 and C7 Enones¹
  作者：Jerry Evarts、Eduardo Torres、Philip L. Fuchs

  DOI：10.1021/ja026760m

  日期：2002.9.1

  Enantiopure epoxyvinyl sulfones SS-9a, SS-9b, produced from Jacobsen epoxidation of 2-phenylsulfonyl 1,3-cyclohexa- and cycloheptadiene, are used as a template for the construction of substituted cycloalkenones and as chiral synthetic equivalents of enones a and b. The addition of carbon nucleophiles to SS-9a, SS-9b is high yielding and stereospecific. Enantiopure alpha,beta- and gamma-substituted cycloalkenones are easily constructed using a variety of methods.
• Synthesis of the C1–C20 and C15–C27 Segments of Aplyronine A
  作者：Wan Pyo Hong、Mohammad N. Noshi、Ahmad El-Awa、Philip L. Fuchs

  DOI：10.1021/ol2024746

  日期：2011.12.16

  The synthesis of C1-C20 and C15-C27 segments of Aplyronine A is described. Oxidative cleavage of cyclic vinyl sulfones has been used to prepare key fragments of Aplyronine A. Key precursors are united by Horner-Wadsworth-Emmons and Julia-Kociensky olefination for the respective elaboration of the C1-C20 and C15-C27 segments.
• Conversion of Cyclic Vinyl Sulfones to Transposed Vinyl Phosphonates
  作者：Mohammad N. Noshi、Ahmad El-awa、Eduardo Torres、Philip L. Fuchs

  DOI：10.1021/ja072890p

  日期：2007.9.1

  Functionalized cyclic vinyl sulfones were directly converted to the "polarity reversed" vinyl phosphonates through an efficient one pot procedure. Ozonolysis of these vinyl sulfones and vinyl phosphonates furnish complementary sets of termini-differentiated ester-aldehydes. This strategy has been applied for preparation of segments needed for the synthesis of Aplyronine A. The scope and limitations of this transformation were defined.