(1S,4S)-7,7-dimethyl-2-methylidene-1-(trifluoromethylsulfonylsulfanyl)bicyclo[2.2.1]heptane | 196790-53-1

• 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,4S)-7,7-dimethyl-2-methylidene-1-(trifluoromethylsulfonylsulfanyl)bicyclo[2.2.1]heptane
• CAS: 196790-53-1
• 化学式: C₁₁H₁₅F₃O₂S₂
• 分子量: 300.366
• InChiKey: PODXHBYAPMJUHP-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,4S)-7,7-dimethyl-2-methylidene-1-(trifluoromethylsulfonylsulfanyl)bicyclo[2.2.1]heptane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以78%的产率得到(1S,4S)-7,7-dimethyl-2-methylidenebicyclo[2.2.1]heptane-1-thiol
  参考文献：
  名称：

  Enantiospecific synthesis of substituted 1-norbornyl trifluoromethanethiosulfonates and 1-norbornanethiols

  摘要：

  New homochiral 1-norbomylthiotriflates 6 and 7 and 1-norbomanethiols 8 and 9 are easily prepared starting from naturally occurring 2-norbomanones 1. The key step is the reaction of chiral 2-norbomanethiones 2 with Tf2O under mild conditions. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00343-1
• 作为产物：
  描述：

  (1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮 在 劳森试剂 、 2,3,5-三碘苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 (1S,4S)-7,7-dimethyl-2-methylidene-1-(trifluoromethylsulfonylsulfanyl)bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Enantiospecific synthesis of substituted 1-norbornyl trifluoromethanethiosulfonates and 1-norbornanethiols

  摘要：

  New homochiral 1-norbomylthiotriflates 6 and 7 and 1-norbomanethiols 8 and 9 are easily prepared starting from naturally occurring 2-norbomanones 1. The key step is the reaction of chiral 2-norbomanethiones 2 with Tf2O under mild conditions. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00343-1

文献信息

• Enantiospecific synthesis of substituted 1-norbornanesulfonic acids and 1-norbornanesulfenic and sulfonic acid derivatives
  作者：Antonio Garcı́a Martı́nez、Enrique Teso Vilar、Florencio Moreno Jiménez、Marı́a Garcı́a Amo

  DOI：10.1016/s0957-4166(00)00122-1

  日期：2000.5

  homochiral 1-norbornanesulfenic and sulfonic acid derivatives 2–7, as well as the sulfonic acids 8, are easily synthesised starting from 2-methylene-1-norbornylthiotriflates 1. This new class of homochiral bridgehead thiosulfonates was prepared by us from naturally occurring (+)-camphor and (−)-fenchone. Nucleophilic substitution at the sulfenyl sulfur atom is the key step for this synthetic strategy

  新纯手性1- norbornanesulfenic和磺酸衍生物2 - 7，以及作为磺酸8，容易合成从2-亚甲基-1- norbornylthiotriflates开始1。此类新的同型手性桥头硫代磺酸盐是由我们从天然存在的（+）-樟脑和（-）-芬酮制备的。在亚硫基硫原子上的亲核取代是该合成策略的关键步骤。
• A novel and simple procedure for the enantiospecific synthesis of bridgehead norbornane thioethers and thiocyanates
  作者：Antonio Garcı́a Martı́nez、Enrique Teso Vilar、Florencio Moreno Jiménez、Ana Marı́a Álvarez Garcı́a、Patricia Pinilla Rodrı́guez

  DOI：10.1016/s0957-4166(02)00716-4

  日期：2002.12
• A short and convenient procedure for the stereoselective synthesis of 2-hydroxy-1-norbornanesulfonamides
  作者：Antonio Garcı́a Martı́nez、Enrique Teso Vilar、Florencio Moreno Jiménez、Ana Marı́a Álvarez Garcı́a

  DOI：10.1016/j.tetasy.2003.10.023

  日期：2004.1

  A short and convenient procedure for the stereoselective synthesis of novel optically active 2-hydroxy-1-norbornanesulfonamides starting from commercially available natural camphor and fenchone is reported. The synthetic route involves a nucleophilic substitution at the sulfenyl sulfur atom of 2-methylene-1-norbornylthiotriflates followed by oxidation of the intermediate sulfenamides and highly diastereoselective reduction of the carbonyl group of the parent 2-oxo-1-norbornanesulfonamides. (C) 2003 Elsevier Ltd. All rights reserved.
• Enantiospecific synthesis of substituted 1-norbornyl trifluoromethanethiosulfonates and 1-norbornanethiols
  作者：Antonio García Martínez、Enrique Teso Vilar、Florencio Moreno Jiménez、Carlota Martínez Bilbao

  DOI：10.1016/s0957-4166(97)00343-1

  日期：1997.9

  New homochiral 1-norbomylthiotriflates 6 and 7 and 1-norbomanethiols 8 and 9 are easily prepared starting from naturally occurring 2-norbomanones 1. The key step is the reaction of chiral 2-norbomanethiones 2 with Tf2O under mild conditions. (C) 1997 Published by Elsevier Science Ltd.