(1S,4S)-N-benzyl-10-camphorsulfonamide | 36217-89-7

• 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)-N-benzyl-10-camphorsulfonamide
• 英文别名: (1S,4R)-N-benzyl-10-camphorsulfonamide；N-benzylcamphor-10-sulfonamide；N-benzyl-10-camphorsulfonylamide；(1S,4S)-(N-benzyl)-(2-keto-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonamide；(1S)-2-oxo-N-benzyl-bornanesulfonamide-(10)；(1S)-2-Oxo-N-benzyl-bornansulfonamid-(10)；N-benzyl-1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonamide
• CAS: 36217-89-7
• 化学式: C₁₇H₂₃NO₃S
• 分子量: 321.441
• InChiKey: VVHBCEVRBDZMBZ-RHSMWYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,4S)-N-benzyl-10-camphorsulfonamide 在 盐酸 、 titanium(III) chloride 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 生成 (1S,2R,4R)-N-benzyl-2-amino-7,7-dimethylbicyclo[2.2.1]hept-1-ylmethanesulfonamide
  参考文献：
  名称：

  [EN] A PROCESS FOR THE MANUFACTURE OF CHIRAL CATALYSTS AND THEIR SALTS
  [FR] PROCÉDÉ POUR LA FABRICATION DE CATALYSEURS CHIRAUX ET DE LEURS SELS

  摘要：

  公开号：

  WO2013080049A3
• 作为产物：
  描述：

  溴甲苯 、 (+/-)-8,8-dimethyl-4,5,6,7-tetrahydro-3ar,6c-methano-benz[c]isothiazole-2,2-dioxide 在 lithium diisopropyl amide 作用下， 生成 (1S,4S)-N-benzyl-10-camphorsulfonamide
  参考文献：
  名称：

  （樟脑磺酰基）亚胺二价阴离子在合成新型光学纯（樟脑磺酰基）恶唑烷衍生物中的作用

  摘要：

  通过使（樟脑磺酰基）亚胺的二价阴离子在邻近磺酰基的碳原子上单烷基化来制备新的，更有效的对映体纯的（樟脑磺酰基）恶唑烷。

  DOI：

  10.1016/s0040-4039(00)99534-0
• 作为试剂：
  描述：

  diethylzinc 、 苯甲醛 在 titanium(IV) isopropylate 、 (1S,4S)-N-benzyl-10-camphorsulfonamide 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-(+)-1-苯基-1-丙醇 、 S(-)-1-苯基-1-丙醇
  参考文献：
  名称：

  Synthesis, structure and activity of sulfonamides derived from (+)-camphor in the enantioselective addition of diethylzinc to benzaldehyde

  摘要：

  New chiral sulfonamides derived from (+)-camphor, with different substituents on camphor C2 and sulfonamide N, were synthesized. Their activity was tested in the reaction of Et2Zn addition to benzaldehyde. The yield of the reaction was 44-96%, the enantiomeric excess was 1-69%. Sulfonamides possessing the 2-hydroxyl group gave an excess of 1-(S)-phenylpropanol, while catalysts containing other sulfonamides gave 1-(R)-phenylpropanol as a major product. The best catalytic efficacy was observed for sulfonamides with (R)-C2-OH group, while the use of thioketo- and mercaptosulfonamides resulted in low enantiomeric excess and yields not exceeding 60%. Crystal structures have been determined for sulfonamides with N-benzyl moiety and different substituents on the C2 atom. The structural analysis revealed the presence of intramolecular N center dot center dot center dot O(C2) and O-sulfo center dot center dot center dot O(C2)H-bonds, what confirms the ability of these molecules to adopt the conformation required for their bidentate coordination to Ti(IV) via the sulfonamide group and substituent at C2. The coordination mode for investigated sulfonamides was determined with the IR spectra for five obtained Ti(IV) complexes and crystal structure analysis of the ligands. The 3D structures of Ti(IV) complex catalysts containing investigated sulfonamides were postulated, which are consistent with the reported chirality of the addition product and observed % ee. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2010.04.019

文献信息

• Regio- and Stereoselective Hydroamidation of 1-Alkynylphosphine Sulfides Catalyzed by Cesium Base
  作者：Azusa Kondoh、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1021/ol8010979

  日期：2008.7.17

  stereoselective hydroamidation of 1-alkynylphosphine sulfides proceeds in the presence of cesium carbonate to provide (E)-2-amino-1-thiophosphinyl-1-alkenes. Asymmetric hydrogenation of the adducts catalyzed by an iridium complex followed by desulfidation yields 2-amino-1-phosphinoalkanes, which offers a new approach to chiral N,P-ligands that will potentially serve as ligands in asymmetric reactions.

  1-炔基膦硫化物的区域和立体选择性加氢酰胺化在碳酸铯的存在下进行，以提供（E）-2-氨基-1-硫代膦基-1-烯烃。铱络合物催化加合物的不对称加氢反应，然后进行脱硫反应，生成2-氨基-1-膦基烷烃，为手性N，P-配体提供了一种新的方法，该方法可能在不对称反应中用作配体。
• Synthesis of novel chiral Schiff bases and their application in asymmetric transfer hydrogenation of prochiral ketones
  作者：Zhongqiang Zhou、Yongjun Bian

  DOI：10.1002/hc.20494

  日期：2008.11

  Novel chiral Schiff bases were synthesized from (+)-camphor, and their application to asymmetric transfer hydrogenation of prochiral ketones is described. The asymmetric transfer hydrogenation reaction could afford excellent conversion rates (up to 97.3%) and up to 27.3% enantiomeric excess. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:682–687, 2008; Published online in Wiley InterScience (www

  由 (+)-樟脑合成了新型手性席夫碱，并描述了它们在前手性酮的不对称转移氢化中的应用。不对称转移氢化反应可以提供优异的转化率（高达 97.3%）和高达 27.3% 的对映体过量。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:682–687, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20494
• Synthesis of camphorsulfonamide-based quinoline ligands and their N-oxides: first use in the enantioselective addition of organozinc reagents to aldehydes
  作者：Ricardo Martínez、Luca Zoli、Pier Giorgio Cozzi、Diego J. Ramón、Miguel Yus

  DOI：10.1016/j.tetasy.2008.10.020

  日期：2008.11

  The preparation of several camphorsulfonamide-based quinoline derivatives and their N-oxides was accomplished via an indirect Friedländer synthesis using aminobenzylic alcohols and RuCl2(DMSO)4 as a catalyst. These ligands were tested in the enantioselective addition of dialkylzinc reagents to aldehydes, with enantiomeric excesses up to 96%. A similar protocol using triphenylborane and diethylzinc

  几种基于樟脑磺酰胺的喹啉衍生物及其N-氧化物的制备，是通过使用氨基苄醇和RuCl 2（DMSO）4作为催化剂的间接Friedländer合成完成的。在二烷基锌试剂对醛的对映选择性加成中，对这些配体进行了测试，对映体过量最高达96％。使用三苯基硼烷和二乙基锌的类似方案给出了相应的苯化过程。
• Camphordisulfonamides: good chiral ligands for the addition of dialkylzinc to aliphatic aldehydes
  作者：Oscar Prieto、Diego J Ramón、Miguel Yus

  DOI：10.1016/s0957-4166(00)00100-2

  日期：2000.4

  preparation of several disulfonamides derived from camphor and their use in the titanium tetraisopropoxide-promoted enantioselective addition of dialkylzinc to aldehydes is described. The enantiomeric ratio is up to 98:2, the best results being obtained for aliphatic aldehydes.

  描述了几种由樟脑衍生的二磺酰胺的制备及其在四异丙氧基钛促进的二烷基锌对醛的对映选择性加成中的用途。对映体比例高达98：2，对于脂族醛而言，可获得最佳结果。
• PROCESS FOR THE MANUFACTURE OF CHIRAL CATALYSTS AND THEIR SALTS
  申请人：Scinopharm Taiwan, LTD.

  公开号：US20130150574A1

  公开（公告）日：2013-06-13

  The present invention provides efficient and economical methods for synthesis of (−)-2-exo-morpholinoisoborne-10-thiol, its enantiomer, and related chiral catalysts. Novel compounds and methods of asymmetric synthesis are also disclosed.

  本发明提供了合成(−)-2-exo-morpholinoisoborne-10-thiol及其对映异构体和相关手性催化剂的高效经济方法。还公开了新型化合物和不对称合成方法。