{2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester | 689284-01-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester
• CAS: 689284-01-3
• 化学式: C₂₃H₃₅Cl₃N₂O₇Si
• 分子量: 585.985
• InChiKey: LVLBYYABEBXFHT-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  106.56
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  {2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester 在 吡啶 、 三乙烯二胺 、 双(乙腈)氯化钯(II) 、 草酰氯 、 TEA 、 溶剂黄146 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (11S,11aS)-2-((E)-2-Dimethylcarbamoyl-vinyl)-11-hydroxy-7,8-dimethoxy-5-oxo-11,11a-dihydro-1H,5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carboxylic acid 2,2,2-trichloro-ethyl ester
  参考文献：
  名称：

  A novel approach to the synthesis of cytotoxic C2–C3 unsaturated pyrrolo[2,1-c]benzodiazepines (PBDs) with conjugated acrylyl C2-substituents

  摘要：

  A concise synthesis of three novel C2-C3 unsaturated pyrrolo[2,1-c][1,4]benzodiazepine analogues (18-20) containing conjugated acrylyl C2-substituents is reported that utilises Heck coupling to install the C2-acrylyl side chains. These analogues possess significant cytotoxicity according to the NO 60-cell line screen with 18 surpassing anthramycin (1) in potency. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.094
• 作为产物：
  描述：

  (5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-(4,5-dimethoxy-2-nitro-benzoyl)pyrrolidin-3-ol 在 吡啶 、 镍 、 肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 {2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester
  参考文献：
  名称：

  A novel approach to the synthesis of cytotoxic C2–C3 unsaturated pyrrolo[2,1-c]benzodiazepines (PBDs) with conjugated acrylyl C2-substituents

  摘要：

  A concise synthesis of three novel C2-C3 unsaturated pyrrolo[2,1-c][1,4]benzodiazepine analogues (18-20) containing conjugated acrylyl C2-substituents is reported that utilises Heck coupling to install the C2-acrylyl side chains. These analogues possess significant cytotoxicity according to the NO 60-cell line screen with 18 surpassing anthramycin (1) in potency. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.094