[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (10S,14R)-12,12-dimethyl-11,13-dioxa-1-azatetracyclo[7.6.0.02,7.010,14]pentadeca-2,4,6,8-tetraene-8-carboxylate | 163776-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (10S,14R)-12,12-dimethyl-11,13-dioxa-1-azatetracyclo[7.6.0.02,7.010,14]pentadeca-2,4,6,8-tetraene-8-carboxylate
• CAS: 163776-60-1
• 化学式: C₂₅H₃₃NO₄
• 分子量: 411.541
• InChiKey: GUQHSHGDGQDAHV-NCRVWVENSA-N

物化性质

• 沸点：
  531.0±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (10S,14R)-12,12-dimethyl-11,13-dioxa-1-azatetracyclo[7.6.0.02,7.010,14]pentadeca-2,4,6,8-tetraene-8-carboxylate 在 lithium hydroxide 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 168.0h， 以53%的产率得到(10S,14R)-12,12-dimethyl-11,13-dioxa-1-azatetracyclo[7.6.0.02,7.010,14]pentadeca-2,4,6,8-tetraene-8-carboxylic acid
  参考文献：
  名称：

  Asymmetric approaches to 1,2-disubstituted mitosenes based on the intramolecular cyclization of diazoesters

  摘要：

  A strategy for the asymmetric synthesis of 1,2-disubstituted mitosenes is described. The key reaction is the decomposition of a meso diazoester in the presence of chiral copper(I) catalysts. Cyclization of diazoesters derived from (1R, 2S, 5R)-menthol and (R)-pantolactone provide optically pure 1,2-disubstituted mitosenes following oxidation and purification by flash chromatography. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01033-8
• 作为产物：
  描述：

  2-硝基苯乙酸 在 palladium on activated charcoal 、 四氧化锇 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 、 S-4,5-二氢-2-(2-((S)-4,5-二氢-4-异丙基噁唑-2-基)丙-2-基)-4-异丙基噁唑 草酰氯 、 4 A molecular sieve 、 氢气 、 sodium hexamethyldisilazane 、 碳酸氢钠 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 N,N-二甲基甲酰胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 、 苯 为溶剂， -78.0~20.0 ℃ 、275.79 kPa 条件下， 反应 67.7h， 生成 [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (10S,14R)-12,12-dimethyl-11,13-dioxa-1-azatetracyclo[7.6.0.02,7.010,14]pentadeca-2,4,6,8-tetraene-8-carboxylate
  参考文献：
  名称：

  Asymmetric approaches to 1,2-disubstituted mitosenes based on the intramolecular cyclization of diazoesters

  摘要：

  A strategy for the asymmetric synthesis of 1,2-disubstituted mitosenes is described. The key reaction is the decomposition of a meso diazoester in the presence of chiral copper(I) catalysts. Cyclization of diazoesters derived from (1R, 2S, 5R)-menthol and (R)-pantolactone provide optically pure 1,2-disubstituted mitosenes following oxidation and purification by flash chromatography. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01033-8

文献信息

• Burgess, Kevin; Lim, Hee-Jong; Porte, Alexander M., Angewandte Chemie, 1996, vol. 108, # 2, p. 192 - 194
  作者：Burgess, Kevin、Lim, Hee-Jong、Porte, Alexander M.、Sulikowski, Gary A.

  DOI：——

  日期：——
• Asymmetric approaches to 1,2-disubstituted mitosenes based on the intramolecular cyclization of diazoesters
  作者：Sangku Lee、Hee-Jong Lim、Kobpurn Lulu Cha、Gary A. Sulikowski

  DOI：10.1016/s0040-4020(97)01033-8

  日期：1997.12

  A strategy for the asymmetric synthesis of 1,2-disubstituted mitosenes is described. The key reaction is the decomposition of a meso diazoester in the presence of chiral copper(I) catalysts. Cyclization of diazoesters derived from (1R, 2S, 5R)-menthol and (R)-pantolactone provide optically pure 1,2-disubstituted mitosenes following oxidation and purification by flash chromatography. (C) 1997 Elsevier Science Ltd.