1,6-anhydro-2-chloro-β-D-erythro-hex-3-enopyranose | 161365-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 1,6-anhydro-2-chloro-β-D-erythro-hex-3-enopyranose
• 英文别名: (1S,4R,5R)-4-chloro-6,8-dioxabicyclo[3.2.1]oct-2-ene
• CAS: 161365-77-1
• 化学式: C₆H₇ClO₂
• 分子量: 146.573
• InChiKey: BTFPGQMVQBKZDY-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2-chloro-β-D-erythro-hex-3-enopyranose 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-O-benzyl-1,6:2,3-dianhydro-β-D-allopyranoside
  参考文献：
  名称：

  Synthesis of 1,6-Anhydro-2-chloro-2,3,4-trideoxy-b-D-erythro-hex-3-enopyranose and Its Stereospecific SN2' Substitution

  摘要：

  The chlorination of 1,6-anhydro-3,4-dideoxy-beta-D-threo-hex-3-enopyranose (2) with SOCl2 and pyridine gives predominantly 1,6-anhydro-2-chloro-beta-D-erythro-hex-3-enopyranose (3). The chloride (3) takes place exclusively the suprafacial SN2' substitution with a variety of nucleophiles in DMF. ''Cerny epoxides'' are conveniently synthesized by using the reaction of 3 with PhCH2ONa.

  DOI：

  10.3987/com-94-6864
• 作为产物：
  描述：

  1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose 在 吡啶 、 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 (1R,2S,5R)-2-chloro-6,8-dioxabicyclo[3.2.1]oct-3-ene 、 1,6-anhydro-2-chloro-β-D-erythro-hex-3-enopyranose 、 (1S,4S,5R)-4-chloro-6,8-dioxabicyclo[3.2.1]oct-2-ene
  参考文献：
  名称：

  Synthesis of 1,6-Anhydro-2-chloro-2,3,4-trideoxy-b-D-erythro-hex-3-enopyranose and Its Stereospecific SN2' Substitution

  摘要：

  The chlorination of 1,6-anhydro-3,4-dideoxy-beta-D-threo-hex-3-enopyranose (2) with SOCl2 and pyridine gives predominantly 1,6-anhydro-2-chloro-beta-D-erythro-hex-3-enopyranose (3). The chloride (3) takes place exclusively the suprafacial SN2' substitution with a variety of nucleophiles in DMF. ''Cerny epoxides'' are conveniently synthesized by using the reaction of 3 with PhCH2ONa.

  DOI：

  10.3987/com-94-6864

文献信息

• Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions
  作者：Martyn Jevric、Julian Klepp、Johannes Puschnig、Oscar Lamb、Christopher J Sumby、Ben W Greatrex

  DOI：10.3762/bjoc.20.74

  日期：——

  Abstract A skeletal rearrangement of a series of 6,8-dioxabicyclo[3.2.1]octan-4-ols has been developed using SOCl2 in the presence of pyridine. An oxygen migration from C5 to C4 was observed when the C4 alcohols were treated with SOCl2/pyridine, giving a 2-chloro-3,8-dioxabicyclo[3.2.1]octane ring-system via the chlorosulfite intermediate. Analogous allylic alcohols with endocyclic and exocyclic unsaturations

   抽象的 在吡啶存在下使用 SOCl 2开发了一系列 6,8-二氧杂双环[3.2.1]辛烷-4​​-醇的骨架重排。当C4醇用SOCl 2 /吡啶处理时，观察到氧从C5迁移到C4，通过氯亚硫酸盐中间体得到2-氯-3,8-二氧杂双环[3.2.1]辛烷环系统。具有环内和环外不饱和度的类似烯丙醇进行氯化，而不会由于形成烯丙基阳离子而发生重排。还使用 Appel 条件证明了重排，通过烷氧基三苯基鏻中间体得到了类似的结果。研究了产物的几种反应以显示重排的效用。 Beilstein J. Org. Chem. 2024, 20, 823–829. doi:10.3762/bjoc.20.74
• Synthesis of 1,6-Anhydro-2-chloro-2,3,4-trideoxy-b-D-erythro-hex-3-enopyranose and Its Stereospecific SN2' Substitution
  作者：Masakatsu Matsumoto、Hiromi Ishikawa、Yoshihiro Soya、Takayuki Ozawa

  DOI：10.3987/com-94-6864

  日期：——

  The chlorination of 1,6-anhydro-3,4-dideoxy-beta-D-threo-hex-3-enopyranose (2) with SOCl2 and pyridine gives predominantly 1,6-anhydro-2-chloro-beta-D-erythro-hex-3-enopyranose (3). The chloride (3) takes place exclusively the suprafacial SN2' substitution with a variety of nucleophiles in DMF. ''Cerny epoxides'' are conveniently synthesized by using the reaction of 3 with PhCH2ONa.