(-)-(1S)-camphor-10,2-sultam

• 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
• 英文名称: (-)-(1S)-camphor-10,2-sultam
• 英文别名: (1S)-(-)-2,10-camphorsultam；(1S,5R,7S)-10,10-dimethyl-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide；(1S,5R,7S)-10,10-dimethyl-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide
• 化学式: C₁₀H₁₇NO₂S
• 分子量: 215.316
• InChiKey: DPJYJNYYDJOJNO-QXFUBDJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(1S)-camphor-10,2-sultam 在 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 四丁基氟化铵 、 zinc trifluoromethanesulfonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 28.0h， 生成 (3aS,6R,7aR)-1-(5-((dibenzylamino)methyl)-3,4-dihydro-2H-pyran-6-yl)-8,8-dimethylhexahydro-3H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide
  参考文献：
  名称：

  路易斯酸用N，O-胺催化炔醇的亲电子氨基甲基氧化环化反应。

  摘要：

  路易斯酸能使炔醇与N，O-缩醛胺进行亲电子的碳氧环化反应。新工艺在非常温和的条件下通过与经典碳金属化相反的途径高效进行。这些反应表现出广泛的底物通用性和官能团相容性，从而导致各种带有不同官能团的5-8元氧杂环。环化产物可通过简单的官能团转化进行精制，以生成合成上有用的氧杂环。

  DOI：

  10.1021/acs.orglett.9b04630

文献信息

• Synthetic Studies of Trichloroleucine Marine Natural Products. Michael Addition of LiCCl₃ to <i>N</i>-Crotonylcamphor Sultam
  作者：Sarah E. Brantley、Tadeusz F. Molinski

  DOI：10.1021/ol991256g

  日期：1999.12.1

  Conjugate addition of trichloromethyllithium to N-crotonylcamphorsultam occurs in good yield at -98 degrees C in THF-hexanes, The formal incorporation of the "CCl3-" anion by 1,4-addition allows subsequent transformation to useful trichloromethyl-substituted intermediates.
• Synthesis of enantiomerically pure HIP-A and HIP-B and investigation of their activity as inhibitors of excitatory amino acid transporters
  作者：Andrea Pinto、Paola Conti、Marco De Amici、Lucia Tamborini、Giovanni Grazioso、Simona Colleoni、Tiziana Mennini、Marco Gobbi、Carlo De Micheli

  DOI：10.1016/j.tetasy.2008.03.001

  日期：2008.4

  The present report deals with the synthesis of the two couples of enantiomers (+)-(3aS,4R,6aS)-/(-)-(3aR,4S,6aR)-3-hydroxy-3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-4-carboxylic acid [(+)-HIP-A and (-)-HIP-A] and (+)-(3aS,6S,6aS)-/(-)-(3aR,6R,6aR)3-hydroxy-3a,4,6,6a-tetrahydro-pyrrolo[3,4-d] isoxizole-6-carboxylic acid [(+)-HIP-B and (-)-HIP-B], and the investigation of their inhibitory activity at EAATs. When tested in a [3 H]D-aspartate uptake assay on native EAATs present in rat brain synaptosomal fractions, (-)-HIP-A and (+)-HIP-B turned Out to be considerably more potent than their enantiomers; in particular, (-)-HIP-A showed an eudismic ratio (ER) higher than 100. Molecular modeling investigations gave clues with regard to the key amino acid residues involved in the binding with our inhibitors and provided explanations for the observed stereo selectivity. (C) 2008 Elsevier Ltd. All rights reserved.
• Lewis Acid Catalyzed Electrophilic Aminomethyloxygenative Cyclization of Alkynols with <i>N</i>,<i>O</i>-Aminals
  作者：Anrong Chen、Houjian Yu、Jiaqi Yan、Hanmin Huang

  DOI：10.1021/acs.orglett.9b04630

  日期：2020.1.17

  Lewis acid enables the electrophilic carbooxygenative cyclization of alkynols with N,O-aminals. The new process proceeds efficiently under very mild conditions via a pathway that is opposite to classical carbo-metalation. These reactions exhibit broad substrate generality and functional group compatibility, leading to a wide variety of 5-8-membered oxacycles bearing diverse functional groups. The cyclization

  路易斯酸能使炔醇与N，O-缩醛胺进行亲电子的碳氧环化反应。新工艺在非常温和的条件下通过与经典碳金属化相反的途径高效进行。这些反应表现出广泛的底物通用性和官能团相容性，从而导致各种带有不同官能团的5-8元氧杂环。环化产物可通过简单的官能团转化进行精制，以生成合成上有用的氧杂环。