benzyl (benzyl){2-[2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl]-2-(1H-indol-3-yl)ethyl}carbamate | 307002-62-6

• 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: benzyl (benzyl){2-[2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl]-2-(1H-indol-3-yl)ethyl}carbamate
• 英文别名: benzyl N-benzyl-N-[2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-(1H-indol-3-yl)ethyl]carbamate
• CAS: 307002-62-6
• 化学式: C₃₁H₃₀N₂O₆
• 分子量: 526.589
• InChiKey: FQMSIVSVWQSDLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (benzyl){2-[2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl]-2-(1H-indol-3-yl)ethyl}carbamate 在 palladium on activated charcoal TEA 、 二苯基膦叠氮化物 、 氢气 作用下， 以 乙醇 、 甲苯 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 109.0h， 生成 (+/-)-cis-3-amino-1-benzyl-4-(1H-indol-3-yl)pyrrolidin-2-one
  参考文献：
  名称：

  A Convenient Synthesis of Indole-Substituted 2-Pyrrolidones and Their Cyclized Derivatives

  摘要：

  Condensation between indole, Meldrum's acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a-c. The latter were cyclized to indole-substituted 2-pyrrolidones 15a-b or 3-aminopyrrolid-2-ones 18a-b, depending on the starting material. Derivative 18a was transformed into pyrrolo[3',4' :5,6]pyrido[3,4-b]indol-3(2H)-ones 19a and 20a by a Pictet-Spengler condensation with benzaldehyde.

  DOI：

  10.1002/1099-0690(200009)2000:17<3051::aid-ejoc3051>3.0.co;2-3
• 作为产物：
  描述：

  2,2-dimethoxy-N-(phenylmethylene)-1-ethanamine 在 DL-脯氨酸 盐酸 、 sodium tetrahydroborate 、 水 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 水 、 乙腈 为溶剂， 反应 58.0h， 生成 benzyl (benzyl){2-[2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl]-2-(1H-indol-3-yl)ethyl}carbamate
  参考文献：
  名称：

  A Convenient Synthesis of Indole-Substituted 2-Pyrrolidones and Their Cyclized Derivatives

  摘要：

  Condensation between indole, Meldrum's acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a-c. The latter were cyclized to indole-substituted 2-pyrrolidones 15a-b or 3-aminopyrrolid-2-ones 18a-b, depending on the starting material. Derivative 18a was transformed into pyrrolo[3',4' :5,6]pyrido[3,4-b]indol-3(2H)-ones 19a and 20a by a Pictet-Spengler condensation with benzaldehyde.

  DOI：

  10.1002/1099-0690(200009)2000:17<3051::aid-ejoc3051>3.0.co;2-3

文献信息

• A Convenient Synthesis of Indole-Substituted 2-Pyrrolidones and Their Cyclized Derivatives
  作者：Michel Boisbrun、Laurent Jeannin、Loïc Toupet、Jean-Yves Laronze

  DOI：10.1002/1099-0690(200009)2000:17<3051::aid-ejoc3051>3.0.co;2-3

  日期：2000.9

  Condensation between indole, Meldrum's acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a-c. The latter were cyclized to indole-substituted 2-pyrrolidones 15a-b or 3-aminopyrrolid-2-ones 18a-b, depending on the starting material. Derivative 18a was transformed into pyrrolo[3',4' :5,6]pyrido[3,4-b]indol-3(2H)-ones 19a and 20a by a Pictet-Spengler condensation with benzaldehyde.