(S)-(+)-(2-甲基丙烯酰)-2,10-樟脑磺内酰胺 | 128441-99-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (S)-(+)-(2-甲基丙烯酰)-2,10-樟脑磺内酰胺
• 英文名称: (3aR-(3aα,6α,7aβ))-hexahydro-8,8-dimethyl-1-(2-methyl-1-oxo-2-propenyl)-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide
• 英文别名: (S)-(+)-(2-Methylacryloyl)-2,10-camphorsultam；1-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-methylprop-2-en-1-one
• CAS: 128441-99-6
• 化学式: C₁₄H₂₁NO₃S
• 分子量: 283.392
• InChiKey: BALAVPVKVQRBKA-MJVIPROJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-(2-甲基丙烯酰)-2,10-樟脑磺内酰胺 生成 [(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-[(5R)-3-(1,3-dioxolan-2-yl)-5-methyl-4H-1,2-oxazol-5-yl]methanone
  参考文献：
  名称：

  CURRAN, DENNIS P.;HEFFNER, TIMOTHY A., J. ORG. CHEM., 55,(1990) N5, C. 4515-4595

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-camphorsultam 、 甲基丙烯酰氯 在 sodium hydride 作用下， 生成 (S)-(+)-(2-甲基丙烯酰)-2,10-樟脑磺内酰胺
  参考文献：
  名称：

  On the scope of asymmetric nitrile oxide cycloadditions with Oppolzer's chiral sultam. Total syntheses of (+)-hepialone, (-)-(1R,3R,5S)-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane, and (-)-(1S)-7,7-dimethyl-6,8-dioxabicyclo[3.2.1]octane

  摘要：

  DOI：

  10.1021/jo00302a023

文献信息

• Copper-Catalyzed Intermolecular Trifluoromethylazidation of Alkenes: Convenient Access to CF₃-Containing Alkyl Azides
  作者：Fei Wang、Xiaoxu Qi、Zhaoli Liang、Pinhong Chen、Guosheng Liu

  DOI：10.1002/anie.201309991

  日期：2014.2.10

  A novel copper‐catalyzed intermolecular trifluoromethylazidation of alkenes has been developed under mild reaction conditions. A variety of CF3‐containing organoazides were directly synthesized from a wide range of olefins, including activated and unactivated alkenes, and the resulting products can be easily transformed into the corresponding CF3‐containing amine derivatives.

  在温和的反应条件下，开发了一种新型的铜催化的烯烃分子间三氟甲基叠氮化反应。可从多种烯烃（包括活化和未活化的烯烃）直接合成各种含CF 3的有机叠氮化物，并且可以轻松地将所得产物转化为相应的含CF 3的胺衍生物。
• Asymmetric Synthesis of Cyclopentene Compounds Containing All-Carbon Quaternary Stereocenters by (3 + 2) Cycloaddition and Its Application in the Formal Synthesis of (<i>R</i>)-(−)-Puraquinonic Acid
  作者：Miho Oga、Yusei Takamatsu、Akihiro Ogura、Ken-ichi Takao

  DOI：10.1021/acs.joc.2c00753

  日期：2022.7.1

  A highly stereoselective (3 + 2) cycloaddition for the asymmetric synthesis of versatile cyclopentene compounds containing all-carbon quaternary stereocenters was developed. The phosphine-catalyzed reactions of alkynoates with α-alkylated electron-deficient alkenes bearing Oppolzer’s camphorsultam showed high to excellent diastereoselectivities and perfect regioselectivities. The usefulness of this

  开发了一种高度立体选择性 (3 + 2) 环加成，用于不对称合成含有全碳四元立体中心的通用环戊烯化合物。炔酸酯与带有 Oppolzer 樟脑磺胺的 α-烷基化缺电子烯烃的膦催化反应显示出高至优异的非对映选择性和完美的区域选择性。( R )-(-)-puraquinonic 酸的简明形式合成证明了该反应的有用性。
• Metal-free visible-light-induced hydroxy-perfluoroalkylation of conjugated olefins using enamine catalyst
  作者：Koto Tagami、Yu Ofuji、Tadashi Kanbara、Tomoko Yajima

  DOI：10.1039/d2ra06679c

  日期：——

  We developed a simple and sustainable method for the hydroxy-perfluoroalkylation of electron-deficient conjugated olefins and styrenes. In this protcol, in situ generated enamine forms electron-donor–accepter (EDA) complexes with perfluoroalkyl iodide, and reaction proceed with visible-light irradiation. Tertiary amine also interacts with perfluoroalkyl iodide via halogen-bonding, promoting the perfluoroalkyl

  我们为缺电子共轭烯烃和苯乙烯的羟基全氟烷基化开发了一种简单且可持续的方法。在该方案中，原位生成的烯胺与全氟烷基碘形成电子供体-受体 (EDA) 络合物，反应在可见光照射下进行。叔胺还通过卤素键与全氟烷基碘相互作用，促进全氟烷基自由基的产生。该反应不需要任何过渡金属或光氧化还原催化剂，气态氧用作绿色羟基源。此外，可以耐受各种市售底物和全氟烷基碘，以良好至中等收率（> 50 个实例，高达 90%）提供所需的羟基-全氟烷基化产物。
• Asymmetric Dipolar Cycloadditions of Me₃SiCHN₂. Synthesis of a Novel Class of Amino Acids:  Azaprolines
  作者：Michael R. Mish、Francisco M. Guerra、Erick M. Carreira

  DOI：10.1021/ja971708p

  日期：1997.9.1
• Photoinduced radical hydroperfluoroalkylation and the synthesis of fluorinated amino acids and peptides
  作者：Tomoko Yajima、Kanako Yamaguchi、Rie Hirokane、Emiko Nogami

  DOI：10.1016/j.jfluchem.2013.02.019

  日期：2013.6

  The photoinduced radical hydroperfluoroalkylation of unsaturated carboxylic acids using TTMSS as a H-donor was successfully developed. The stereoselective reaction using Oppolzer's camphorsultum was also achieved to give high stereoselectivity. The reaction was also effective for N-phthalimide-dehydroamino acid and the product was easily converted to the corresponding amino acid and a peptide derivative. (C) 2013 Elsevier B.V. All rights reserved.