ethyl 1,1-bis(benzyloxymethyl)cyclopropane-2-carboxylate | 145215-00-5

• 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: ethyl 1,1-bis(benzyloxymethyl)cyclopropane-2-carboxylate
• 英文别名: ethyl 2,2-bis(benzyloxymethyl)cyclopropanecarboxylate；Ethyl 2,2-bis((benzyloxy)methyl)cyclopropane-1-carboxylate；ethyl 2,2-bis(phenylmethoxymethyl)cyclopropane-1-carboxylate
• CAS: 145215-00-5
• 化学式: C₂₂H₂₆O₄
• 分子量: 354.446
• InChiKey: YABGPZKAYVGSIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1,1-bis(benzyloxymethyl)cyclopropane-2-carboxylate 在 氢氧化钾 、 sodium azide 、 氯甲酸乙酯 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 甲苯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Syntheses of 2,2-bishydroxymethylcyclopropyl adenine and uracil, novel carbocyclic nucleosides

  摘要：

  Novel carbocyclic nucleoside, 2,2-bishydroxymethylcyclopropyl adenine and uracil were successfully synthesized.

  DOI：

  10.1016/s0040-4039(00)71258-5
• 作为产物：
  描述：

  苯甲醇 在 rhodium(II) acetate dimer 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 13.5h， 生成 ethyl 1,1-bis(benzyloxymethyl)cyclopropane-2-carboxylate
  参考文献：
  名称：

  [EN] SMALL MOLECULE INHIBITORS OF KRAS G12D MUTANT
  [FR] INHIBITEURS À PETITES MOLÉCULES DE MUTANT DE KRAS G12D

  摘要：

  化合物或其药学上可接受的盐可以抑制Kirsten大鼠肉瘤（KRAS）蛋白的G12D突变，并预计具有治疗剂的效用，例如，用于治疗癌症。本公开还提供了包含此处披露的化合物或其药学上可接受的盐的制药组合物。本公开还涉及使用该化合物或其药学上可接受的盐在癌症治疗和预防以及为此目的制备制药的方法。

  公开号：

  WO2022221739A1

文献信息

• Highly functionalized donor–acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids
  作者：Alexander F.G. Goldberg、Robert A. Craig、Nicholas R. O’Connor、Brian M. Stoltz

  DOI：10.1016/j.tetlet.2014.09.016

  日期：2015.6

  A series of highly substituted vinylcyclopropanes were prepared and examined as reaction partners in a palladium-catalyzed (3+2) cycloaddition with nitrostyrenes. Described herein are our efforts to synthesize an elusive 1,1-divinylcyclopropane by several distinct approaches, and to apply surrogates of this fragment toward the synthesis of the Melodious alkaloids. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of carbocyclic nucleosides: synthesis of (±)-2,2-bis(hydroxymethyl)cyclopropyl nucleosides
  作者：Takao Izawa、Shigeru Nishiyama、Shosuke Yamamura、Kuniki Kato、Tomohisa Takita

  DOI：10.1039/p19920002519

  日期：——

  Treatment of 2,2-bis(benzyloxymethyl)cyclopropanecarboxylic acid 8 with ethyl chloroformate and sodium azide followed by thermolysis of the resulting keto azide 9 at 80-degrees-C provided the corresponding isocyanate 10, which was then converted into 2,2-bis(benzyloxymethyl)cyclopropylurea 11 and 2, 2-bis(benzyloxymethyl)cyclopropylamine 13. The racemic 2,2-bis(hydroxymethyl)cyclopropylpyrimidine nucleosides 16, 21, 22, 23, 26, 29, and 31 and the purine nucleosides 39 and 41 were prepared from compounds 11 and 13, respectively; they showed no antiviral activity against HSV-1, HSV-2, HCMV, and HIV-1 in cell culture.
• A Short Total Synthesis of (±)-Epimeloscine and (±)-Meloscine Enabled by a Cascade Radical Annulation of a Divinylcyclopropane
  作者：Hanmo Zhang、Dennis P. Curran

  DOI：10.1021/ja2042854

  日期：2011.7.13

  The first stereoselective synthesis of epimeloscine has been accomplished in 13 total steps with a longest linear sequence of 10 steps. The core of the synthesis takes only five steps, the key ones being acylation, stereoselective tandem radical cyclization of a divinylcyclopropane to make two rings, and group-selective ring-closing metathesis of the resulting divinylcyclopentane to make the last ring.
• Syntheses of 2,2-bishydroxymethylcyclopropyl adenine and uracil, novel carbocyclic nucleosides
  作者：Shigeru Nishiyama、Shinya Ueki、Tatsuya Watanabe、Shosuke Yamamura、Kuniki Kato、Tomohisa Takita

  DOI：10.1016/s0040-4039(00)71258-5

  日期：1991.5

  Novel carbocyclic nucleoside, 2,2-bishydroxymethylcyclopropyl adenine and uracil were successfully synthesized.
• [EN] SMALL MOLECULE INHIBITORS OF KRAS G12D MUTANT<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DE MUTANT DE KRAS G12D
  申请人：MERCK SHARP & DOHME

  公开号：WO2022221739A1

  公开（公告）日：2022-10-20

  Compounds or their pharmaceutically acceptable salts can inhibit the G12D mutant of Kirsten rat sarcoma (KRAS) protein and are expected to have utility as therapeutic agents, for example, for treating cancer. The disclosure also provides pharmaceutical compositions which comprise compounds disclosed herein or pharmaceutically acceptable salts thereof. The disclosure also relates to methods for use of the compounds or their pharmaceutically acceptable salts in the therapy and prophylaxis of cancer and for preparing pharmaceuticals for this purpose.

  化合物或其药学上可接受的盐可以抑制Kirsten大鼠肉瘤（KRAS）蛋白的G12D突变，并预计具有治疗剂的效用，例如，用于治疗癌症。本公开还提供了包含此处披露的化合物或其药学上可接受的盐的制药组合物。本公开还涉及使用该化合物或其药学上可接受的盐在癌症治疗和预防以及为此目的制备制药的方法。