(Z)-(SS,2S)-1-Nitro-2-<(2-phenylpropyl)sulfinyl>-1-propene | 142467-44-5

• 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: (Z)-(SS,2S)-1-Nitro-2-<(2-phenylpropyl)sulfinyl>-1-propene
• 英文别名: [(2S)-1-[(S)-[(Z)-1-nitroprop-1-en-2-yl]sulfinyl]propan-2-yl]benzene
• CAS: 142467-44-5
• 化学式: C₁₂H₁₅NO₃S
• 分子量: 253.322
• InChiKey: KGUZYVAUHHCMRU-AMVHXXFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-(SS,2S)-1-Nitro-2-<(2-phenylpropyl)sulfinyl>-1-propene 在 间氯过氧苯甲酸 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 34.0h， 生成 (1S,4R,5S,6R)-5-methyl-6-nitro-5-[(2S)-2-phenylpropyl]sulfonylbicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  Diastereoselective Diels-Alder Cycloadditions with Chiral 1-(Alkylsulfinyl)-2-nitroalkenes

  摘要：

  Several chiral 2-nitro-1-sulfinylalkenes were prepared and examined for their utility as dienophiles for asymmetric [4 + 2] cycloaddition. Trisubstituted dienophiles 3-6 undergo diastereoselective cycloaddition with cyclopentadiene in the presence of Lewis acids. Even the tetrasubstituted chiral sulfinyl dienophiles 1 and 2 could be coerced into undergoing [4 + 2] cycloaddition to afford the cycloadducts in high yield without concomitant elimination if the reaction was conducted under high pressure. Generally, the Z-sulfinyl dienophiles 1-4 showed higher diastereo- and endo/exo-selectivity than;the E-dienophiles 5 and 6.

  DOI：

  10.1021/jo00087a043
• 作为产物：
  描述：

  (S)-2-苯基丙硫醇 在 Oxone 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.02h， 生成 (Z)-(SS,2S)-1-Nitro-2-<(2-phenylpropyl)sulfinyl>-1-propene
  参考文献：
  名称：

  Diastereoselective Diels-Alder Cycloadditions with Chiral 1-(Alkylsulfinyl)-2-nitroalkenes

  摘要：

  Several chiral 2-nitro-1-sulfinylalkenes were prepared and examined for their utility as dienophiles for asymmetric [4 + 2] cycloaddition. Trisubstituted dienophiles 3-6 undergo diastereoselective cycloaddition with cyclopentadiene in the presence of Lewis acids. Even the tetrasubstituted chiral sulfinyl dienophiles 1 and 2 could be coerced into undergoing [4 + 2] cycloaddition to afford the cycloadducts in high yield without concomitant elimination if the reaction was conducted under high pressure. Generally, the Z-sulfinyl dienophiles 1-4 showed higher diastereo- and endo/exo-selectivity than;the E-dienophiles 5 and 6.

  DOI：

  10.1021/jo00087a043

文献信息

• Diastereoselective Diels-Alder reactions with chiral sulfinyl derivatives as dienophiles under high pressure
  作者：Kaoru Fuji、Kiyoshi Tanaka、Hitoshi Abe、Kiyoshi Matsumoto、Tooru Taga、Yoshihisa Miwa

  DOI：10.1016/s0957-4166(00)82293-4

  日期：1992.5

  Using the high pressure technique, asymmetric Diels-Alder reaction utilizing chiral 2-nitro-1-sulfinylolefins and dienes proceeded smoothly to give highly functionalized cyclohexene derivatives with satisfactory chemical yield and high diastereomeric excess.
• Diastereoselective Diels-Alder Cycloadditions with Chiral 1-(Alkylsulfinyl)-2-nitroalkenes
  作者：Kaoru Fuji、Kiyoshi Tanaka、Hitoshi Abe、Kiyoshi Matsumoto、Takashi Harayama、Atsutoshi Ikeda、Tooru Taga、Yoshihisa Miwa、Manabu Node

  DOI：10.1021/jo00087a043

  日期：1994.4

  Several chiral 2-nitro-1-sulfinylalkenes were prepared and examined for their utility as dienophiles for asymmetric [4 + 2] cycloaddition. Trisubstituted dienophiles 3-6 undergo diastereoselective cycloaddition with cyclopentadiene in the presence of Lewis acids. Even the tetrasubstituted chiral sulfinyl dienophiles 1 and 2 could be coerced into undergoing [4 + 2] cycloaddition to afford the cycloadducts in high yield without concomitant elimination if the reaction was conducted under high pressure. Generally, the Z-sulfinyl dienophiles 1-4 showed higher diastereo- and endo/exo-selectivity than;the E-dienophiles 5 and 6.