-1-(2-phenylpropylsulfinyl)-2-nitrocyclopentene | 129396-35-6

• 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: -1-(2-phenylpropylsulfinyl)-2-nitrocyclopentene
• 英文别名: (S(S),2S)-1-(2-phenylpropylsulfinyl)-2-nitrocyclopentene；[(2S)-1-[(S)-(2-nitrocyclopenten-1-yl)sulfinyl]propan-2-yl]benzene
• CAS: 129396-35-6
• 化学式: C₁₄H₁₇NO₃S
• 分子量: 279.36
• InChiKey: SHQHTMGVIXGCAQ-WYRIXSBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  -1-(2-phenylpropylsulfinyl)-2-nitrocyclopentene 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 40.17h， 生成
  参考文献：
  名称：

  Enantioselective construction of highly functionalized bicyclo[4.3.0] system through Diels-Alder cycloaddition

  摘要：

  The Diels-Alder reaction of chiral 2-alkylsulfinyl-1-nitroalkene 4 with Danishefsky`s diene afforded adducts 9a and 10a in good chemical yield with a high enantiomeric excess, while diastereomeric nitroalkene 5 gave 9b and 10b, enantiomeric to 9a and 10a, respectively. The synthesis of the chiral dienophiles and mechanism of the chiral induction in the cycloaddition are discussed.

  DOI：

  10.1016/s0957-4166(00)80029-4
• 作为产物：
  描述：

  1-硝基环戊烯 在 Oxone 、 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.33h， 生成 -1-(2-phenylpropylsulfinyl)-2-nitrocyclopentene
  参考文献：
  名称：

  Enantioselective construction of highly functionalized bicyclo[4.3.0] system through Diels-Alder cycloaddition

  摘要：

  The Diels-Alder reaction of chiral 2-alkylsulfinyl-1-nitroalkene 4 with Danishefsky`s diene afforded adducts 9a and 10a in good chemical yield with a high enantiomeric excess, while diastereomeric nitroalkene 5 gave 9b and 10b, enantiomeric to 9a and 10a, respectively. The synthesis of the chiral dienophiles and mechanism of the chiral induction in the cycloaddition are discussed.

  DOI：

  10.1016/s0957-4166(00)80029-4

文献信息

• Addition-elimination strategy for asymmetric induction: A chiral sulfoxide as a leaving group
  作者：Kaoru Fuji、Manabu Node、Hitoshi Abe、Akichika Itoh、Yukio Masaki、Motoo Shiro

  DOI：10.1016/s0040-4039(00)97377-5

  日期：1990.1

  The reaction of β-nitro-α,β-unsaturated sulfoxide 7 with δ-lactam enolates 11 – 15 afforded 20 – 24, respectively, in good chemical yields with high enantiomeric excesses.

  β硝基-α的反应中，β -不饱和亚砜7与δ内酰胺烯醇化物11 - 15，得到20 - 24分别，在具有高对映体过量良好的化学产率。
• 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.
• Asymmetric diels-alder cycloaddition with chiral 2-alkylsulfinyl-1-nitroalkenes
  作者：Kaoru Fuji、Kiyoshi Tanaka、Hitoshi Abe、Akichika Itoh、Manabu Node、Tooru Taga、Yoshihisa Miwa、Motoo Shiro

  DOI：10.1016/s0957-4166(00)82353-8

  日期：1991.1

  The Diels-Alder reaction of chiral 2-alkylsulfinyl-1-nitroalkene 1 and Danishefsky's diene (2) afforded adducts 3 and 4 in good chemical yield with a high enantiomeric excess, while diastereomeric nitroalkene 7 gave 8 and 9, enantiomeric to 3 and 4, respectively.
• 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.