10-N,N-dicyclohexylosulfamoyl-(2R)-isobornyl glyoxylate | 379685-55-9

• 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: 10-N,N-dicyclohexylosulfamoyl-(2R)-isobornyl glyoxylate
• 英文别名: 10-N,N-dicyclohexylsulphamoyl-(R)-isobornyl glyoxalate；10-N,N-dicyclohexylsulphamoyl-(2R)-isobornyl glyoxylate；10-N,N-dicyclohexylsulfamoyl-(R)-isobornyl glyoxylate；[(1S,2R,4R)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-oxoacetate
• CAS: 379685-55-9
• 化学式: C₂₄H₃₉NO₅S
• 分子量: 453.643
• InChiKey: GNSYGHNFSBWILV-MEKIYTOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  10-N,N-dicyclohexylosulfamoyl-(2R)-isobornyl glyoxylate 在 锌 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 36.0h， 生成 N-[(2'R)-N'-p-toluenesulfonyl-3',3'-dimethylallylglycine]-10-N,N-dicyclohexylsulfamoyl (2R)-isobornyl ester
  参考文献：
  名称：

  手性 N-甲苯亚胺的非对映选择性 Barbier 型加成

  摘要：

  Barbier 方法用于烯丙基氨基酸衍生物的非对映选择性形成。对带有各种手性助剂的 N-甲苯磺酰亚胺进行亲核加成的立体化学模型，例如 (2R)-bomano-10,2-sultam、(R)-8-phenylmenthol 和 10-N,N-dicyclohexylsulfamoyl-(R)-isobomeol被提议。

  DOI：

  10.1055/s-2003-41453
• 作为产物：
  描述：

  (-)-10-dicyclohexylsulfamoyl-D-isoborneol 在 三正丙胺 、 2-氯-1-甲基吡啶碘化物 、 臭氧 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 10-N,N-dicyclohexylosulfamoyl-(2R)-isobornyl glyoxylate
  参考文献：
  名称：

  The asymmetric hetero-Diels–Alder reaction and addition of allylic organometallics to 10-N,N-dicyclohexylsulphamoyl-(2R)-isobornyl glyoxylate

  摘要：

  The recent development of very effective chiral auxiliaries has led to the design of 10-N,N-dicyclohexylsulphamoyl-(R)-isoborneol, which is similar to Oppolzer's (2R)-bornane-10,2-sultam but less effective on account of a less rigid structure. 10-N,N-Dicyclohexylsulphamoyl-(R)-isobornyl glyoxylate was examined in Diels-Alder and organometallic addition reactions. The results obtained were compared with those achieved by application of N-glyoxyloyl-(2R)-bornane-10,2-sultam. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00212-8

文献信息

• The synthesis of oximes and nitroalkanes bearing a chiral auxiliary unit: convenient substrates for the preparation of enantiomerically pure nitrile oxides
  作者：Iwona Kudyba、Julita Jóźwik、Jan Romański、Jerzy Raczko、Janusz Jurczak

  DOI：10.1016/j.tetasy.2005.05.025

  日期：2005.7

  We report the synthesis of four new oximes and three nitroalkanes bearing a chiral unit. All these compounds were converted into nitrile oxides and subjected to 1,3-dipolar cycloaddition with 3-E-hexene, giving the corresponding 2-isoxazolines in fair yields but only with moderate stereoselectivities.

  我们报道了带有手性单元的四种新肟和三种硝基烷的合成。所有这些化合物均转化为腈氧化物，并与3- E-己烯进行1,3-偶极环加成反应，以适当的收率得到相应的2-异恶唑啉，但仅具有中等的立体选择性。
• Diastereoselectivity in the hetero [4+2] cycloaddition of cyclopentadiene to N-benzyliminoacetyl derivatives of (2R)-bornane-10,2-sultam and other chiral secondary alcohols
  作者：Sławomir Szymański、Christian Chapuis、Janusz Jurczak

  DOI：10.1016/s0957-4166(01)00356-1

  日期：2001.7

  Various protonated chiral glyoxyloyl-alpha -imino-N-benzyl hetero-dienophiles have been examined in the diastereoselective exo-cycloaddition to cyclopentadiene at -78 degreesC promoted by CF3CO2-BF3, a dissociated non-nucleophilic counter ion. The best pi -facial selectivities were observed with (2R)-bornane-10,2-sultam (76% d.e.) and (2R)-10-dicyclohexylsulfonamoyl-isoborneol (80% d.e.) as chiral auxiliaries. These conditions were found to be superior in terms of yields and selectivities as compared to analogous aza-dienophiles treated with simple Lewis acids or under thermal conditions. Absolute configurations were assigned on the basis of an X-ray analysis of the major cycloadduct (3 'S)-3a as well as by chiroptical comparison with the corresponding new amino alcohol (-)-(3S)-4a. Plausible transition states are briefly discussed on the basis of PM3 conformational calculations. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Diastereoselective allylation of chiral imines and a stereocontrolled route to 4-hydroxy-N-tosylpipecolic acid derivatives
  作者：Anna Kulesza、Adam Mieczkowski、Janusz Jurczak

  DOI：10.1016/s0957-4166(02)00542-6

  日期：2002.9

  We report an asymmetric route to non-proteogenic amino acids, based on Lewis acid-mediated diastereoselective additions of allyltrimethylsilane to iminoglyoxylic acid derivatives bearing ester or amide chiral auxiliaries. Reactions of allyltrimethylsilane with N-tosyl- and N-phenyliminoglyoxylates of (R)-8-phenylmenthol proceeded with excellent diastereoselectivity (d.e. 98%). In contrast, the reactions of N-benzyliminoglyoxylates occurred with low diastereoselectivities and in poor yields. We have applied our methodology to develop a short synthesis of (2S,4R)-4-hydroxypipecolic acid derivatives. (C) 2002 Published by Elsevier Science Ltd.
• Asymmetric addition of titanium and sodium alkoxides to chiral imines
  作者：Anna Kulesza、Adam Mieczkowski、Jan Romański、Janusz Jurczak

  DOI：10.1016/s0957-4166(03)00121-6

  日期：2003.5

  A novel method for the alkoxylation of imines was developed using alkoxytitanium(IV) derivatives as the alkoxy nucleophile donors. A rationale of the results obtained using stereochemical models is proposed. The differences in the stereochemical outcome of the reaction with the titanium species and sodium alkoxides were studied as well as the influence of chiral auxiliaries such as (2R)-bornano-10,2-sultam, (R)-8-phenylmenthol and 10-N,N-dicyclohexylsulphamoyl-(R)-isoborneol. (C) 2003 Elsevier Science Ltd. All rights reserved.
• The Diastereoselective Barbier-Type Addition to Chiral<i>N</i>-Tosylimines
  作者：Janusz Jurczak、Anna Kulesza

  DOI：10.1055/s-2003-41453

  日期：——

  The Barbier approach was used for diastereoselective formation of allylamino acid derivatives. The stereochemical models for nucleophilic addition to N-tosylimines bearing various chiral auxiliaries such as (2R)-bomano-10,2-sultam, (R)-8-phenylmenthol, and 10-N,N-dicyclohexylsulfamoyl-(R)-isobomeol are proposed.

  Barbier 方法用于烯丙基氨基酸衍生物的非对映选择性形成。对带有各种手性助剂的 N-甲苯磺酰亚胺进行亲核加成的立体化学模型，例如 (2R)-bomano-10,2-sultam、(R)-8-phenylmenthol 和 10-N,N-dicyclohexylsulfamoyl-(R)-isobomeol被提议。