(R)-N-[(2-furyl)phenylmethyl]-4-methylbenzenesulfonamide | 158568-79-7

• 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: (R)-N-[(2-furyl)phenylmethyl]-4-methylbenzenesulfonamide
• 英文别名: N-[(R)-furan-2-yl(phenyl)methyl]-4-methylbenzenesulfonamide
• CAS: 158568-79-7
• 化学式: C₁₈H₁₇NO₃S
• 分子量: 327.404
• InChiKey: DDWQDUCHSJIPET-GOSISDBHSA-N

物化性质

• 熔点：
  134-136 °C
• 沸点：
  468.3±55.0 °C(predicted)
• 密度：
  1.241±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯硼酸酐 、 2-furaldehyde tosylimine 在 2C₂₉H₂₆NP*Cl₂Rh₂ 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.0h， 以83%的产率得到(R)-N-[(2-furyl)phenylmethyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  新的手性磷-烯烃双齿配体的设计与合成及其在铑催化的向N-磺酰基亚胺的有机硼氧烷类不对称加成反应中的应用。

  摘要：

  新型的手性磷-烯烃双齿配体已由易于获得的对映纯化合物经数步合成。这些配体已被用于铑催化的将有机硼氧烷酮不对称加成到N-磺酰基醛亚胺上，从而实现了高收率和对映选择性。

  DOI：

  10.1039/c1cc11823d

文献信息

• Tertiary Amine-Triggered Cascade S_N2/Cycloaddition: An Efficient Construction of Complex Azaheterocycles under Mild Conditions
  作者：Jian Hu、Bing Tian、Xinyan Wu、Xiaofeng Tong

  DOI：10.1021/ol302329b

  日期：2012.10.5

  In this paper, an amine-triggered cascade SN2/cycloaddtion sequence between 2-(acetoxymethyl)buta-2,3-dienoate 1 and various π-system functionalized tosylamides 3 has been reported, which provides a facile method for stereoselective construction of structurally diverse azaheterocycles.

  在本文中，已经报道了在2-（乙酰氧基甲基）丁2,3-二烯酸酯1和各种π-系统官能化的甲苯磺酰胺3之间的胺触发级联S N 2 /环加成序列，为立体选择性构建Sn 2提供了一种简便的方法。结构上不同的氮杂杂环。
• An N-Linked Bidentate Phosphoramidite Ligand (N-Me-BIPAM) for Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to N-Sulfonylarylaldimines
  作者：Kazunori Kurihara、Yasunori Yamamoto、Norio Miyaura

  DOI：10.1002/adsc.200800631

  日期：2009.1

  A chiral N-linked C2-symmetric bidentate phosphoramidite (N-Me-BIPAM) was newly developed for the rhodium-catalyzed enantioselective addition of arylboronic acids to N-sulfonylimines. This ligand achieved high enantioselectivities in a range of 84–99% ee in additions of arylboronic acids to N-tosyl- and N-nosylarylaldimines.

  手性N-连接的C 2-对称的二齿亚磷酰胺（N -Me-BIPAM）是新开发的，用于铑催化的对N-磺酰亚胺基的芳基硼酸的对映选择性加成。除了在N-甲苯磺酰基和N-壬基芳基醛亚胺中添加芳基硼酸外，该配体还实现了84-99％ee范围内的高对映选择性。
• Enantioselective Synthesis of Arylglycine Derivatives by Asymmetric Addition of Arylboronic Acids to Imines
  作者：Yasunori Yamamoto、Yoshinori Takahashi、Kazunori Kurihara、Norio Miyaura

  DOI：10.1071/ch11225

  日期：——

  Rhodium-catalyzed enantioselective 1,2-additions of arylboronic acids to N-tosyl furanylimine and lithium 5-methyl-2-furanyltriolborate to N-tosyl arylimines giving aryl(2-furanyl)methanamines were developed for enantioselective synthesis of arylglycines by ozonolysis of the furyl ring. A chiral N-linked C2-symmetric bidentate phosphoramidite (N-Me-BIPAM) achieved high enantioselectivities up to 99 % ee. For the direct synthesis of arylglycines, the asymmetric addition of arylboronic acids to ethyl N-p-methoxyphenyl iminoester was carried out at 80°C in dioxane in the presence of Rh(acac)(C2H4)2/(R,R)-N-Me-BIPAM. The reaction gave optically active arylglycines in up to 99 % ee.

  在铑催化下，芳基硼酸与 N-对甲苯磺酰基呋喃亚胺发生 1,2 对映体加成反应，5-甲基-2-呋喃三醇硼酸锂与 N-对甲苯磺酰基芳基亚胺发生 1,2 对映体加成反应，生成芳基（2-呋喃基）甲胺。一种手性 N-连接的 C2 对称双叉磷酰胺（N-Me-BIPAM）实现了高达 99 % ee 的高对映选择性。为了直接合成芳基甘氨酸，在 Rh(acac)(C2H4)2/(R,R)-N-Me-BIPAM 的存在下，芳基硼酸与 N-对甲氧基苯基亚胺酯乙酯在 80°C 的二噁烷中进行了不对称加成反应。反应生成了具有光学活性的芳基甘氨酸，ee高达 99%。
• Enantioselective Rh-Catalyzed Arylation of <i>N</i>-Tosylarylimines with Arylboronic Acids
  作者：Hai-Feng Duan、Yi-Xia Jia、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1021/ol060755w

  日期：2006.6.1

  The asymmetric arylation of N-tosylarylimines with arylboronic acids was realized by using rhodium/(S)-ShiP as catalyst. The reaction proceeded in aqueous toluene to give diarylmethylamines in good yields with up to 96% ee.
• Catalytic Enantioselective Arylation of <i>N</i>-Tosylarylimines with Arylboronic Acids Using <i>C</i>₂-Symmetric Cationic <i>N</i>-Heterocyclic Carbene Pd²⁺ Diaquo Complexes
  作者：Guang-Ning Ma、Tao Zhang、Min Shi

  DOI：10.1021/ol802861s

  日期：2009.2.19

  The asymmetric arylation of N-tosylimines with arylboronic acids was realized by using chiral cationic C-2-symmetric N-heterocyclic carbene (NHC) Pd2+ diaquo complex 5b as the catalyst in combination with 1.0 equiv of K3PO4 center dot 3H(2)O in THF at 4 degrees C in the presence of powdered 4 angstrom MS to afford the corresponding adducts in excellent yields (up to 99%) and good to high enantioselectivities (up to 94% ee).