(1S)-(+)-N,N-diisopropyl-10-camphorsulfonamide | 96323-05-6

• 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
• 英文名称: (1S)-(+)-N,N-diisopropyl-10-camphorsulfonamide
• 英文别名: (S)-Camphorsulfonic acid diisopropylamide；1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]-N,N-di(propan-2-yl)methanesulfonamide
• CAS: 96323-05-6
• 化学式: C₁₆H₂₉NO₃S
• 分子量: 315.477
• InChiKey: YVTXGMUWKRUQFM-CZUORRHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-(+)-N,N-diisopropyl-10-camphorsulfonamide 在 三氟化硼乙醚 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 85.5h， 生成 (1S,2S,5'S)-N,N-diisopropyl {2-spiro-2'-[5'-phenyl-5'-(prop-2''-enyl)-1',3'-dioxolane-4'-one]-7,7-dimethylbicyclo[2.2.1]hept-1-yl}methanesulfonamide
  参考文献：
  名称：

  Enantioselective Synthesis of α-Hydroxy Acids Employing (1S)-(+)-N,N-Diisopropyl-10-camphorsulfonamide as Chiral Auxiliary

  摘要：

  [GRAPHICS]Lewis acid (BF3. OEt2) catalyzed condensation of dimethoxy acetal 2 with alpha-hydroxy acids produces chiral 1,3-dioxolanones I. The enolates derived from these compounds undergo reactions with alkyl halides with a high level of diastereoselectivity. Subsequent hydrolysis of these alkylated products II gives mono- and disubstituted alpha-hydroxy acids III with high enantiomeric excesses.

  DOI：

  10.1021/ol9910666
• 作为产物：
  描述：

  D(+)-10-樟脑磺酸 在 4-二甲氨基吡啶 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1S)-(+)-N,N-diisopropyl-10-camphorsulfonamide
  参考文献：
  名称：

  CAMPHOR-DERIVED COMPOUNDS, METHOD FOR MANUFACTURING THE SAME, AND APPLICATION THEREOF

  摘要：

  揿脑素衍生化合物的结构如下式（I）所示： 其中R1、R2、R3和R4分别如规范中所述定义。此外，还公开了一种制造揿脑素衍生化合物和应用它们的方法。

  公开号：

  US20120077976A1

文献信息

• Methylenephenylsulfone appended acetals and ketals: New class of carbonyl protective groups cleavable by DBU
  作者：S. Chandrasekhar、Sanjita Sarkar

  DOI：10.1016/s0040-4039(98)00209-3

  日期：1998.4

  propane diol, readily obtainable by dihydroxylation of commercially available allylphenylsulfone, acts as an efficient and new protection reagent for both aldehydes and ketones. This protective group is elegantly removed by use of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), under nonaqueous conditions.

  通过对市售的烯丙基苯基砜进行二羟基化可以很容易地获得3-苯基磺酰基1,2-丙二醇，它是醛和酮的一种有效的新型保护剂。在非水条件下，通过使用1,8-二氮杂双环[5.4.0] -7-十一碳烯（DBU）可以优雅地除去该保护基。
• Process for preparing optically active &agr;-hydroxy acids and derivatives thereof
  申请人：Chan Hardy W.

  公开号：US06639095B1

  公开（公告）日：2003-10-28

  The present invention provides a process for preparing optically active &agr;-hydroxy acids and derivatives thereof by subjecting the alkylated 1,3-dioxolanones of formula (IV) wherein R1 and R2 are the same or different and are each independently H or C1-6 alkyl; R5 is H, C1-16 alkyl, or unsubstituted or substituted phenyl; and R6 is C1-8 alkyl, C2-7 alkenyl or unsubstituted or substituted benzyl, to either alcoholysis or hydrolysis, in which the alkylated 1,3-dioxolanones are obtained by using 10-camphorsulfonamide as a chiral auxiliary.

  本发明提供了一种制备光学活性α-羟基酸及其衍生物的方法，通过将具有化学式（IV）的烷基化1,3-二氧杂环酮暴露于醇解或水解条件下，其中R1和R2相同或不同，分别独立地为H或C1-6烷基；R5为H、C1-16烷基，或未取代或取代的苯基；R6为C1-8烷基、C2-7烯基或未取代或取代的苄基，所述烷基化1,3-二氧杂环酮是通过使用10-樟脑磺酰胺作为手性辅助剂获得的。
• Diastereoselective Conjugate Addition to (+)-Camphorsulfonic Acid Derived Nitroalkenes:  Synthesis of α-Hydroxy and α-Amino Acids
  作者：Anthony G. M. Barrett、D. Christopher Braddock、Paul W. N. Christian、Daniel Pilipauskas、Andrew J. P. White、David J. Williams

  DOI：10.1021/jo980582r

  日期：1998.8.1

  Diastereoselective tandem conjugate addition of both oxygen- and nitrogen-centered nucleophiles to the novel (1S)-10-camphorsulfonic acid derived nitroalkenes 9, 10, and 11 and ozonolysis gave the alpha-hydroxy and alpha-amino thiol acid derivatives 12, 13, and 14. In all cases, the (R)-diastereomer was formed as the major component albeit with only modest levels of selectivity (33-71% de). The structures

  将以氧和氮为中心的亲核试剂非对映选择性串联共轭添加到新型（1S）-10-樟脑磺酸衍生的硝基烯烃9、10和11中，并进行臭氧分解，得到α-羟基和α-氨基硫醇酸衍生物12、13 14.在所有情况下，（R）-非对映异构体都是主要成分，尽管选择性水平适中（33-71％de）。产物的结构和迈克尔加成反应的立体化学是通过硝基烯烃9和10以及（2S）-12c和（2R）-13a的X射线晶体学研究以及通过（S）-丙氨酸的替代合成而明确确定的（S）-缬氨酸和（S）-乳酸乙酯。
• Asymmetric diels-alder reactions : facile preparation and structure of sulfonamido-isobornyl acrylates
  作者：Wolfgang Oppolzer、Christian Chapuis、Gérald Bernardinelli

  DOI：10.1016/s0040-4039(01)81711-1

  日期：1984.1

  The crystalline chiral auxiliaries , and were prepared from camphor-10-sulfonyl chlorides in 2 steps. Their readily accessible acrylates underwent efficient asymmetric diels-alder additions to cyclopentadiene, the topicity of which agrees with X-ray evidence.

  结晶手性助剂，和从樟脑-10-磺酰氯在2个步骤制备。他们容易获得的丙烯酸酯在环​​戊二烯中进行了有效的不对称Diels-Alder加成反应，其局部性与X射线证据相符。
• Electrolytic partial fluorination of organic compounds Part 62
  作者：Daisuke Baba、Yi-Jen Yang、Biing-Jiun Uang、Toshio Fuchigami

  DOI：10.1016/s0022-1139(02)00341-x

  日期：2003.5

  Anodic fluorination of chiral 1,3-oxathiolan-5-ones, derived from camphorsulfonamide and thioglycol acid, was carried out under various conditions. When dimethoxyethane (DME) containing Et4NF·4HF was used, the corresponding monofluororinated products were obtained in good yield as a single diastereomer. Chemical fluorination was also attempted using N-fluoropyridinium salts; however, fluorination did

  在各种条件下，对由樟脑磺酰胺和巯基乙酸衍生的手性1,3-氧杂硫杂环戊烷-5-酮进行阳极氟化。当使用含有Et 4 NF·4HF的二甲氧基乙烷（DME）时，以单一非对映体的高收率获得了相应的单氟代产物。还尝试使用N-氟吡啶鎓盐进行化学氟化；但是，氟化根本没有进行。