(1S)-2-oxo-bornane-10-sulfonic acid o-toluidide | 1239977-91-3

• 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)-2-oxo-bornane-10-sulfonic acid o-toluidide
• 英文别名: (1S)-2-Oxo-bornan-10-sulfonsaeure-o-toluidid；(1S)-2-Oxo-bornan-sulfonsaeure-(10)-o-toluidid；(1S)-2-Oxo-bornan-10-sulfonsaeure-o-toluidid; (d-Campher)-β-sulfonsaeure-o-toluidid；(d-Campher)-β-sulfonsaeure-o-toluidid；(d-Campher)-sulfonsaeure-(1¹)-o-toluidid；1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]-N-(2-methylphenyl)methanesulfonamide
• CAS: 1239977-91-3
• 化学式: C₁₇H₂₃NO₃S
• 分子量: 321.441
• InChiKey: BWUWIAPCSTVYSV-CXAGYDPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  4
• 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)-2-oxo-bornane-10-sulfonic acid o-toluidide 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 以87.5%的产率得到(1S,2R,4S)-N-(2-methylphenyl)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonamide
  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
• 作为产物：
  描述：

  右旋樟脑-10-磺酰氯 、 邻甲苯胺 生成 (1S)-2-oxo-bornane-10-sulfonic acid o-toluidide
  参考文献：
  名称：

  Singh et al., Proceedings - Indian Academy of Sciences, Section A, 1952, vol. 36, p. 440,445

  摘要：

  DOI：

文献信息

• Reliability of the time trade-off technique of utility assessment in patients with retinal disease
  作者：Hussein Hollands、Miu Lam、Joe Pater、Dave Albiani、Gary C. Brown、Melissa Brown、Alan F. Cruess、Sanjay Sharma

  DOI：10.1016/s0008-4182(01)80041-7

  日期：2001.6

  Background: Studies in medical fields other than ophthalmology have given conflicting results regarding the reliability of the time trade-off technique of utility assessment. We performed a study to determine the test-retest reliability of the time trade-off technique for assessing utilities in patients with ocular diseases of the retina and to investigate possible factors associated with differences in utility over time.Methods: Patients referred to the retina service of a tertiary care hospital in eastern Canada were eligible for the initial interview if they had best corrected vision of 20/30 or worse in at least one eye and were deemed competent to answer the required questions. Patients were interviewed prospectively between December 1999 and March 2000 during a normal 30-minute period needed for pharmacologic mydriasis to occur. Demographic, clinical (including Snellen visual acuity) and time trade-off utility information was collected through chart review and standardized interview. Patients who completed the interview successfully were called back 28 days later for follow-up.Results: Of the 138 eligible patients 112 (81.2%) completed the initial interview. Of the 112, 96 (85.7%) completed the second interview. Half of the respondents were women, and all but one respondent were white. The mean age was 65.3 years. The primary reasons for visual loss included diabetic retinopathy (59 patients [61.4%]) and age-related macular degeneration (14 patients [14.6%]). The intraclass correlation coefficient between the initial and follow-up visual utilities was 0.7634 (95% confidence interval 0.6655-0.8355).Interpretation: Our results show excellent reliability of the time trade-off technique of utility assessment in patients with ocular diseases of the retina.
• Singh et al., Proceedings - Indian Academy of Sciences, Section A, 1952, vol. 36, p. 440,445
  作者：Singh et al.

  DOI：——

  日期：——
• Synthesis, structure and activity of sulfonamides derived from (+)-camphor in the enantioselective addition of diethylzinc to benzaldehyde
  作者：Anna Kozakiewicz、Małgorzata Ullrich、Mirosław Wełniak、Andrzej Wojtczak

  DOI：10.1016/j.molcata.2010.04.019

  日期：2010.7

  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.