N-methyl-N-<(1S)-4-oxocycloheptyl>benzamide | 60723-28-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-methyl-N-<(1S)-4-oxocycloheptyl>benzamide
• 英文别名: N-benzoylphysoperuvine；N-Benzoyl physoperuvine；N-methyl-N-[(1S)-4-oxocycloheptyl]benzamide
• CAS: 60723-28-6
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: YSVIQIOQISDMHJ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-cycloheptylbenzamide 在 盐酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 49.58h， 生成 N-methyl-N-<(1S)-4-oxocycloheptyl>benzamide
  参考文献：
  名称：

  Oxygenation of N-cycloheptylbenzamides with Beauveria sulfurescens

  摘要：

  The oxygenation of several N-cycloheptylbenzamides by fermentation with the fungus Beauveria sulfurescens (ATCC 7159) has been studied. Structures have been determined by chemical and physical methods. Enantioselectivity was observed m the oxygenation process, and the absolute configurations of optically active compounds have been determined by circular dichroism spectroscopy, X-ray crystallography, and chemical correlation. Oxygenation of N-cycloheptylbenzamide (1) gave N-[(1S)-4-oxocycloheptyl]benzamide (2) and N-[(1S,4S)-4-hydroxycycloheptyl]benzamide (5). A reverse of enantioselectivity in the oxygenation process was observed with the substrate N-cycloheptyl-N-methylbenzamide (3), the primary product being N-methyl-N-[(1R)-4-oxocycloheptyl]benzamide (4). Chemical conversion of ketone 2 into N-methyl-N-[(1,S)-4-oxocycloheptyl]benzamide (14) confirmed the enantiomeric relationship of the oxygenation products 2 and 4. Enantiomeric excesses of the oxygenation products were not determined since crystallization was used extensively in the purification of crude products.

  DOI：

  10.1021/jo00052a040

文献信息

• Catalytic asymmetrization of meso-3,7-bis-siloxycycloheptene by chiral rhodium(<scp>I</scp>)-binap [2,2′-bis(diphenylphosphino)-1,1′-binaphthyl] catalyst: the enantiocontrolled asymmetric synthesis of (–)-(S)-physoperuvine
  作者：Kou Hiroya、Kunio Ogasawara

  DOI：10.1039/c39950002205

  日期：——

  Catalytic asymmetrization of meso-3,7-bis-tert-butyldimethylsiloxycycloheptene occurs in the presence of a chiral rhodium(I) binap catalyst to give optically active 4-tert-butyldimethylsiloxycycloheptanone in 70% ee after hydrolytic workup, the (R)-enantiomer of which has been transformed into (-)–(S)-physoperuvine, the major alkaloid of Physalis peruviana.

  在手性铑 (I) binap 催化剂存在下，内消旋 3,7-双叔丁基二甲基硅氧基环庚烯发生催化不对称化，水解后得到光学活性的 4-叔丁基二甲基硅氧基环庚酮（70% ee），即 (R)-对映体其中已转化为(-)-(S)-physoperuvine，酸浆的主要生物碱。
• Ray, Anil B.; Oshima, Yoshiteru; Hikino, Hiroshi, Heterocycles, 1982, vol. 19, # 7, p. 1233 - 1236
  作者：Ray, Anil B.、Oshima, Yoshiteru、Hikino, Hiroshi、Kabuto, Chizuko

  DOI：——

  日期：——
• Oxygenation of N-cycloheptylbenzamides with Beauveria sulfurescens
  作者：Roy A. Johnson、Milton E. Herr、Herbert C. Murray、William C. Krueger、Loraine M. Pschigoda、David J. Duchamp

  DOI：10.1021/jo00052a040

  日期：1992.12

  The oxygenation of several N-cycloheptylbenzamides by fermentation with the fungus Beauveria sulfurescens (ATCC 7159) has been studied. Structures have been determined by chemical and physical methods. Enantioselectivity was observed m the oxygenation process, and the absolute configurations of optically active compounds have been determined by circular dichroism spectroscopy, X-ray crystallography, and chemical correlation. Oxygenation of N-cycloheptylbenzamide (1) gave N-[(1S)-4-oxocycloheptyl]benzamide (2) and N-[(1S,4S)-4-hydroxycycloheptyl]benzamide (5). A reverse of enantioselectivity in the oxygenation process was observed with the substrate N-cycloheptyl-N-methylbenzamide (3), the primary product being N-methyl-N-[(1R)-4-oxocycloheptyl]benzamide (4). Chemical conversion of ketone 2 into N-methyl-N-[(1,S)-4-oxocycloheptyl]benzamide (14) confirmed the enantiomeric relationship of the oxygenation products 2 and 4. Enantiomeric excesses of the oxygenation products were not determined since crystallization was used extensively in the purification of crude products.