diethyl (R)-[3-nitro-1-(phenylsulfonyl)pentan-3-yl]phosphonate | 1445598-53-7

• 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: diethyl (R)-[3-nitro-1-(phenylsulfonyl)pentan-3-yl]phosphonate
• 英文别名: diethyl 3-nitro-1-(phenylsulfonyl)pentan-3-ylphosphonate；(R)-diethyl (3-nitro-1-(phenylsulfonyl)pentan-3-yl)phosphonate；[(3R)-3-diethoxyphosphoryl-3-nitropentyl]sulfonylbenzene
• CAS: 1445598-53-7
• 化学式: C₁₅H₂₄NO₇PS
• 分子量: 393.398
• InChiKey: ZFGBPADARCUXRK-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  苯基乙烯基砜 、 1-二乙氧基磷酰-1-硝基-丙烷 在 N-[3,5-双(三氟甲基)苯基]-N′-[(9R)-6′-甲氧基-9-金鸡宁]硫脲 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以98%的产率得到diethyl (R)-[3-nitro-1-(phenylsulfonyl)pentan-3-yl]phosphonate
  参考文献：
  名称：

  Highly Enantioselective Michael Addition of α-Substituted Nitrophosphonates to a Vinyl Sulfone

  摘要：

  Organocatalytic asymmetric Michael reaction of alpha-substituted nitrophosphonates to phenyl vinyl sulfone catalyzed by cinchona alkaloid-derived tertiary amine-thioureas afforded alpha,alpha-disubstituted nitrophosphonates in very good yields and excellent enantiomeric excesses.

  DOI：

  10.1055/s-0033-1338434

文献信息

• Enantioselective Synthesis of α-Amino-γ-sulfonyl Phosphonates with a Tetrasubstituted Chiral α-Carbon<i>via</i>Quinine-Squaramide-Catalyzed Michael Addition of Nitrophosphonates to Vinyl Sulfones
  作者：Kalisankar Bera、Irishi N. N. Namboothiri

  DOI：10.1002/adsc.201300224

  日期：2013.5.3

  α‐Nitro‐γ‐sulfonyl phosphonates with a key tetrasubstituted chiral α‐carbon center have been synthesized for the first time in high yield and enantioselectivity through a quinine‐squaramide‐catalyzed conjugate addition of α‐nitro phosphonates to aryl vinyl sulfones. Representative examples presented here for the transformation of nitrosulfonyl phosphonates to aminosulfonyl phosphonates, alkylation

  具有关键的四取代手性α-碳中心的α-硝基-γ-磺酰基膦酸酯是通过奎宁-方酰胺催化的α-硝基膦酸酯向芳基乙烯基砜的共轭加成反应首次以高收率和对映选择性合成的。这里介绍的有关将硝基磺酰基膦酸酯转化为氨基磺酰基膦酸酯，在磺酰基基团的α位进行烷基化，然后进行脱磺化和扩大共轭物添加量的典型实例突出了该方法的实际应用。
• Highly Enantioselective Michael Addition of α-Substituted Nitrophosphonates to a Vinyl Sulfone
  作者：Yixin Lu、Guo-Ying Chen

  DOI：10.1055/s-0033-1338434

  日期：——

  Organocatalytic asymmetric Michael reaction of alpha-substituted nitrophosphonates to phenyl vinyl sulfone catalyzed by cinchona alkaloid-derived tertiary amine-thioureas afforded alpha,alpha-disubstituted nitrophosphonates in very good yields and excellent enantiomeric excesses.