3-methylene-1,2-bis(hydroxymethyl)cyclopropane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methylene-1,2-bis(hydroxymethyl)cyclopropane
• 英文别名: 1,2-Bis(hydroxymethyl)-3-meth-ylidenecyclopropane；[2-(hydroxymethyl)-3-methylidenecyclopropyl]methanol
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: SUAJNHGXHTVCFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methylene-1,2-bis(hydroxymethyl)cyclopropane 在 吡啶 、 氢氧化钾 、 三溴化磷 作用下， 生成 [3]轴烯
  参考文献：
  名称：

  The Preparation and Properties of Trimethylenecyclopropane

  摘要：

  DOI：

  10.1021/ja00951a067
• 作为产物：
  描述：

  dimethyl 3-methylenecyclopropane-1,2-dicarboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以79%的产率得到3-methylene-1,2-bis(hydroxymethyl)cyclopropane
  参考文献：
  名称：

  SYNTHESIS AND ANTIVIRAL ACTIVITY OF NOVEL EXOMETHYLENE CYCLOPROPYL NUCLEOSIDES

  摘要：

  Novel cyclopropyl nucleosides were synthesized as potential antiviral agents. The key intermediate 5, prepared from Feist's acid 1 was condensed with purine derivatives by the S(N)2 type reaction. All the synthesized compounds were evaluated for antiviral activity.

  DOI：

  10.1081/ncn-100002491

文献信息

• Intermediates and process for the preparation of an antiviral agent
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0736533A1

  公开（公告）日：1996-10-09

  (1R,trans) Diprotected 3-methylene-1,2-cyclopropanedimethanol is oxidized to an optically active diol intermediate which is then cyclized to an orthoester intermediate, and then converted to the (2S-trans)diprotected 2,3-bis(hydroxymethyl)cyclobutanone. This cyclobutanone is useful as an intermediate in the preparation of the antiviral agent [1R-(1α,2β,3α)]-2-amino-9-[2,3-bis(hydroxymethyl)cyclobutyl]-1,9-dihydro-6H-purin-6-one.

  (1R,反式)二保护的 3-亚甲基-1,2-环丙烷二甲醇被氧化成光学活性二元醇中间体，然后环化成正辛酯中间体，再转化成(2S-反式)二保护的 2,3-双(羟甲基)环丁酮。这种环丁酮是制备抗病毒剂[1R-(1α,2β,3α)]-2-氨基-9-[2,3-双（羟甲基）环丁基]-1,9-二氢-6H-嘌呤-6-酮的中间体。
• Desymmetrization of meso-methylenecyclopropanes by a palladium-catalyzed asymmetric ring-opening bis(alkoxycarbonylation) reaction
  作者：Yasushi Yonezawa、Tomoki Furuya、Takahiro Aratani、Shuhei Fijinami、Katsuhiko Inomata、Yutaka Ukaji

  DOI：10.1016/j.tetasy.2014.05.007

  日期：2014.6

  Desymmetrization of various meso-methylenecyclopropanes was accomplished by a palladium-catalyzed asymmetric ring-opening bis(alkoxycarbonylation) reaction employing a chiral bioxazoline ligand. The reaction proceeded smoothly in the presence of copper(I) triflate under carbon monoxide and oxygen at ambient pressure to give the corresponding optically active alpha-methyleneglutarates with up to 60% ee. Desymmetrization of protected meso-(3-methylenecyclopropane-1,2-diyl)dimethanols was also carried out to give enantioenriched highly oxygen-functionalized alpha-methyleneglutarates. (C) 2014 Elsevier Ltd. All rights reserved.
• US4988703A
  申请人：——

  公开号：US4988703A

  公开（公告）日：1991-01-29
• US5773614A
  申请人：——

  公开号：US5773614A

  公开（公告）日：1998-06-30
• SYNTHESIS AND ANTIVIRAL ACTIVITY OF NOVEL EXOMETHYLENE CYCLOPROPYL NUCLEOSIDES
  作者：Bo Gil Choi、Eun Yee Kwak、Joon Hee Hong、Chong Kyo Lee

  DOI：10.1081/ncn-100002491

  日期：2001.3.31

  Novel cyclopropyl nucleosides were synthesized as potential antiviral agents. The key intermediate 5, prepared from Feist's acid 1 was condensed with purine derivatives by the S(N)2 type reaction. All the synthesized compounds were evaluated for antiviral activity.