3,4-dihydroxy-1,2-epoxy-5-hexene acetonide | 149252-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dihydroxy-1,2-epoxy-5-hexene acetonide
• 英文别名: 1,2-Epoxy-3,4-(dimethylmethylenedioxy)-5-hexene；4-ethenyl-2,2-dimethyl-5-(oxiran-2-yl)-1,3-dioxolane
• CAS: 149252-60-8
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: AKTQXGIWIPHDOK-UHFFFAOYSA-N

物化性质

• 沸点：
  228.5±35.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dihydroxy-1,2-epoxy-5-hexene acetonide 生成 (R)-3-((4R,5R)-2,2-Dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-3-hydroxy-propionitrile
  参考文献：
  名称：

  Cyclohexanetriol derivatives

  摘要：

  环己三醇衍生物的化学式表示为：其中R¹、R²和R³相同或不同，分别表示氢原子或羟基的保护基团，X表示氧原子，=CHCH₂OR⁴，=CHCHO或=CHCO₂R⁵，Y表示氢原子，Z表示-OR⁶，或Y和Z共同形成单键；或X和Z共同形成=NO-，=CHCH(OR⁷)O-或=CHCO₂-，而Y为氢原子，R⁴和R⁶分别表示氢原子或羟基的保护基团，R⁵表示较低的烷基基团，而R⁷表示氢原子或较低的烷基基团。这些衍生物可用作1-羟基维生素D衍生物的合成中间体。

  公开号：

  EP0503630A1
• 作为产物：
  描述：

  2,2-二甲基-4,5-二乙烯基-1,3-二氧戊环 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以85%的产率得到3,4-dihydroxy-1,2-epoxy-5-hexene acetonide
  参考文献：
  名称：

  Regiochemical and stereochemical studies on halogen-induced ring expansions of unsaturated episulfides

  摘要：

  The reactions of unsaturated episulfides with bromine and iodine have been studied. Initially produced in the reaction is a ring opened sulfenyl halide intermediate, which in the presence of the carbon-carbon double bond or triple bond cyclizes to beta,beta'-dihalo sulfide cycloadducts. The regiochemistry and relative stereochemistry of these cyclizations have been examined as a function of the length of the tether between the episulfide moiety and the unsaturated functionality, the presence of alkyl substituents, and the type of unsaturation. A discussion of the mechanistic and stereochemical features of the ring-expansion process is presented.

  DOI：

  10.1021/jo00125a039

文献信息

• Cyclohexanetriol derivatives
  申请人：Kuraray Co., Ltd.

  公开号：EP0503630A1

  公开（公告）日：1992-09-16

  Cyclohexanetriol derivatives represented by the formula wherein    R¹, R² and R³ are the same or different, and each denotes a hydrogen atom or a protecting group of a hydroxyl group,    X denotes an oxygen atom, =CHCH₂OR⁴, =CHCHO or =CHCO₂R⁵, Y denotes a hydrogen atom and Z denotes -OR⁶, or Y and Z together form a single bond; or X and Z together form =NO-, =CHCH(OR⁷)O-or =CHCO₂- and Y is a hydrogen atom, R⁴ and R⁶ denote a hydrogen atom or a protecting group of a hydroxyl group respectively, R⁵ denotes a lower alkyl group, and R⁷ denotes a hydrogen atom or a lower alkyl group. Said derivatives are useful as synthetic intermediates of 1 -hydroxyvitamin D derivatives.

  环己三醇衍生物的化学式表示为：其中R¹、R²和R³相同或不同，分别表示氢原子或羟基的保护基团，X表示氧原子，=CHCH₂OR⁴，=CHCHO或=CHCO₂R⁵，Y表示氢原子，Z表示-OR⁶，或Y和Z共同形成单键；或X和Z共同形成=NO-，=CHCH(OR⁷)O-或=CHCO₂-，而Y为氢原子，R⁴和R⁶分别表示氢原子或羟基的保护基团，R⁵表示较低的烷基基团，而R⁷表示氢原子或较低的烷基基团。这些衍生物可用作1-羟基维生素D衍生物的合成中间体。
• US5334740A
  申请人：——

  公开号：US5334740A

  公开（公告）日：1994-08-02
• Regiochemical and stereochemical studies on halogen-induced ring expansions of unsaturated episulfides
  作者：Xiao-Feng Ren、Monika I. Konaklieva、Edward Turos、Lynn M. Krajkowski、Charles H. Lake、Thomas S. Janik、Melvyn Rowen Churchill

  DOI：10.1021/jo00125a039

  日期：1995.10

  The reactions of unsaturated episulfides with bromine and iodine have been studied. Initially produced in the reaction is a ring opened sulfenyl halide intermediate, which in the presence of the carbon-carbon double bond or triple bond cyclizes to beta,beta'-dihalo sulfide cycloadducts. The regiochemistry and relative stereochemistry of these cyclizations have been examined as a function of the length of the tether between the episulfide moiety and the unsaturated functionality, the presence of alkyl substituents, and the type of unsaturation. A discussion of the mechanistic and stereochemical features of the ring-expansion process is presented.
• Drugs Fut. 2005, 30, 450-461
  作者：

  DOI：——

  日期：——