(11aS)-3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylic acid methyl ester | 792948-25-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: (11aS)-3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylic acid methyl ester
• 英文别名: methyl (E)-3-[(6aS)-3-methyl-6,11-dioxo-4-phenylmethoxy-6a,9-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl]prop-2-enoate
• CAS: 792948-25-5
• 化学式: C₂₄H₂₂N₂O₅
• 分子量: 418.449
• InChiKey: IJOATQKHTLWMLM-JARZOMNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (11aS)-3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylic acid methyl ester 在 hydridochlorotris(triphenylphosphine)ruthenium(II) 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以66%的产率得到3-(9-benzyloxy-8-methyl-5,11-dioxo-10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)propionic acid methyl ester
  参考文献：
  名称：

  Synthetic study of (+)-anthramycin using ring-closing enyne metathesis and cross-metathesis

  摘要：

  Synthesis of (+)-anthramycin was examined. A pyrrolobenzodiazepine skeleton could be synthesized by reductive cyclization of pyrrolidine derivative, which was obtained by enyne metathesis. The conjugated enamide ester part of (+)-anthramycin derivative was constructed by cross-metathesis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.040
• 作为产物：
  描述：

  (S)-4-Vinyl-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester 在 盐酸 、 manganese(IV) oxide 、 sodium chlorite 、 potassium dihydrogenphosphate 、 氯化亚砜 、 2-甲基-2-丁烯 、 [1,3-Mes₂-(N₂C₃H₅)]Cl₂(PCy₃)Ru=CHPh 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 150.33h， 生成 (11aS)-3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylic acid methyl ester
  参考文献：
  名称：

  Synthetic study of (+)-anthramycin using ring-closing enyne metathesis and cross-metathesis

  摘要：

  Synthesis of (+)-anthramycin was examined. A pyrrolobenzodiazepine skeleton could be synthesized by reductive cyclization of pyrrolidine derivative, which was obtained by enyne metathesis. The conjugated enamide ester part of (+)-anthramycin derivative was constructed by cross-metathesis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.040

文献信息

• Methods
  申请人：MEDIMMUNE LIMITED

  公开号：US11352324B2

  公开（公告）日：2022-06-07

  A method of synthesising a compound of formula (I): (I) from a compound of formula (II): (II) where R8 is either: (i) ProtO3; or (ii) a group of formula (A1) in formula (I) and (A2) in formula (II): (A1), (A2).

  一种合成式(I)化合物的方法：(I) 由式(II)化合物合成： (II) 其中 R8 为：(i) ProtO3；或 (ii) 式(I)中的式(A1)和式(II)中的式(A2)基团： (A1)，(A2)。
• METHODS
  申请人：MEDIMMUNE LIMITED

  公开号：US20200399215A1

  公开（公告）日：2020-12-24

  A method of synthesising a compound of formula (I): (I) from a compound of formula (II): (II) where R 8 is either: (i) Prot O3 ; or (ii) a group of formula (A1) in formula (I) and (A2) in formula (II): (A1), (A2).
• Synthetic study of (+)-anthramycin using ring-closing enyne metathesis and cross-metathesis
  作者：Tsuyoshi Kitamura、Yoshihiro Sato、Miwako Mori

  DOI：10.1016/j.tet.2004.07.040

  日期：2004.10

  Synthesis of (+)-anthramycin was examined. A pyrrolobenzodiazepine skeleton could be synthesized by reductive cyclization of pyrrolidine derivative, which was obtained by enyne metathesis. The conjugated enamide ester part of (+)-anthramycin derivative was constructed by cross-metathesis. (C) 2004 Elsevier Ltd. All rights reserved.