(3aR,7aS)-5,6-Dimethyl-3a-nitro-7a-((S)-(S)-2-phenyl-propane-1-sulfinyl)-2,3,3a,4,7,7a-hexahydro-1H-indene | 142467-46-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3aR,7aS)-5,6-Dimethyl-3a-nitro-7a-((S)-(S)-2-phenyl-propane-1-sulfinyl)-2,3,3a,4,7,7a-hexahydro-1H-indene
• CAS: 142467-46-7
• 化学式: C₂₀H₂₇NO₃S
• 分子量: 361.505
• InChiKey: TZWOSAYRQAPISD-WKVINZIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  -1-(2-phenylpropylsulfinyl)-2-nitrocyclopentene 、 2,3-二甲基-1,3-丁二烯 在 对苯二酚 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 以77%的产率得到(3aR,7aS)-5,6-Dimethyl-3a-nitro-7a-((S)-(S)-2-phenyl-propane-1-sulfinyl)-2,3,3a,4,7,7a-hexahydro-1H-indene
  参考文献：
  名称：

  Diastereoselective Diels-Alder reactions with chiral sulfinyl derivatives as dienophiles under high pressure

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)82293-4

文献信息

• 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.