(1R,2S)-rel-3,3-dichloro-1,2-cyclopropanedimethanol | 160321-05-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S)-rel-3,3-dichloro-1,2-cyclopropanedimethanol
• 英文别名: 3,3-dichloro-cis-1,2-dihydroxymethylcyclopropane；cis-1,2-bis(oxymethyl)-3,3-dichlorocyclopropane；cis-3,3-dichlorocyclopropane-1,2-diyldimethanol；(1R,2S)-3,3-dichloro-1,2-cyclopropanedimethanol；[(1R,3S)-2,2-dichloro-3-(hydroxymethyl)cyclopropyl]methanol
• CAS: 160321-05-1
• 化学式: C₅H₈Cl₂O₂
• 分子量: 171.023
• InChiKey: AUOAVOUVRZCQEQ-ZXZARUISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (1R,2S)-rel-3,3-dichloro-1,2-cyclopropanedimethanol 160.0~165.0 ℃ 、2.67 kPa 条件下， 以55%的产率得到6,6-dichloro-3-oxabicyclo<3.1.0>hexane
  参考文献：
  名称：

  环烷羧酸与SF 4的反应。二。宝石-二氯环丙烷羧酸与SF 4的氟化

  摘要：

  用SF 4处理宝石-二氯环丙烷羧酸产生许多重排产物，即1，1-二氟取代的烯烃。讨论了重排的机制。

  DOI：

  10.1016/0022-1139(93)02995-q
• 作为产物：
  描述：

  8',8'-dichlorospiro[cyclohexane-1,4'-[3,5]dioxabicyclo[5.1.0]octane] 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 288.0h， 以81%的产率得到(1R,2S)-rel-3,3-dichloro-1,2-cyclopropanedimethanol
  参考文献：
  名称：

  七元杂环的立体化学：XLVI。螺[环己烷-1,4'-[3,5]二恶双环[5.1.0]辛烷]的合成及13 C NMR动态光谱。结构相关的甲醛和丙酮缩醛的DFT计算

  摘要：

  Spiro[cyclohexane-1,4'-[3,5]dioxabicyclo[5.1.0]octanes] were synthesized, and their conformational behavior was studied by dynamic C-13 NMR spectroscopy. Anancomeric displacement of conformational equilibrium toward two nonequivalent twist conformers with close energies was revealed. The relative Gibbs energies Delta G degrees and enthalpies of formation Delta H degrees of twist and chair-like conformers with endo and exo orientation of the three-membered ring of structurally related formaldehyde and acetone acetals were calculated in terms of the density functional theory at the B3LYP/6-31G(d,p) level. Like spiro-cyclohexane analogs, they were shown to have a non-chair conformation.

  DOI：

  10.1134/s1070428007120196

文献信息

• Conformational stability of diastereomeric 8,8-dichloro-3,5-dioxa-4-thia-4-oxobicyclo[5.1.0]octanes: X-ray crystallography, dynamic 1H and 13C NMR spectroscopy study
  作者：V.V. Gavrilov、M.N. Shamsutdinov、O.N. Kataeva、V.V. Klochkov、I.A. Litvinov、Yu.G. Shtyrlin、E.N. Klimovitskii

  DOI：10.1016/j.molstruc.2007.11.046

  日期：2008.10

  Abstract X-ray data for both title molecules display a chair conformation with exo location of cyclopropane moiety and axial or equatorial sulfinyl group. Dynamic 1H and 13C NMR spectroscopy at −95 °С exhibit conformational homogeneity for the first diastereomer and two component chair – twist-boat equilibrium (2:3) for the latter.

  两个标题分子的摘要 X 射线数据显示椅子构象，环丙烷部分和轴向或赤道亚磺酰基的外部位置。-95 °С 下的动态 1H 和 13C NMR 光谱显示出第一个非对映异构体的构象均匀性和后者的双组分椅子 - 扭船平衡 (2:3)。
• Reactions of cycloalkanecarboxylic acids with SF4. II. Fluorination of gem-dichlorocyclopropanecarboxylic acids with SF4
  作者：Yu.M. Pustovit、P.I. Ogojko、V.P. Nazaretian、A.B. Rozhenko

  DOI：10.1016/0022-1139(93)02995-q

  日期：1994.12

  Treatment of gem-dichlorocyclopropanecarboxylic acids with SF4 yields many rearranged products, i.e. 1,1-difluoro-substituted olefins. The mechanism of the rearrangement is discussed.

  用SF 4处理宝石-二氯环丙烷羧酸产生许多重排产物，即1，1-二氟取代的烯烃。讨论了重排的机制。
• Stereochemistry of seven-membered heterocycles: XLVI. Synthesis and dynamic 13C NMR spectroscopy of spiro[cyclohexane-1,4′-[3,5]dioxabicyclo[5.1.0]octanes]. DFT calculations of structurally related formaldehyde and acetone acetals
  作者：V. V. Gavrilov、M. N. Shamsutdinov、G. A. Chmutova、R. M. Vafina、Yu. G. Shtyrlin、V. V. Klochkov、E. N. Klimovitskii

  DOI：10.1134/s1070428007120196

  日期：2007.12

  Spiro[cyclohexane-1,4'-[3,5]dioxabicyclo[5.1.0]octanes] were synthesized, and their conformational behavior was studied by dynamic C-13 NMR spectroscopy. Anancomeric displacement of conformational equilibrium toward two nonequivalent twist conformers with close energies was revealed. The relative Gibbs energies Delta G degrees and enthalpies of formation Delta H degrees of twist and chair-like conformers with endo and exo orientation of the three-membered ring of structurally related formaldehyde and acetone acetals were calculated in terms of the density functional theory at the B3LYP/6-31G(d,p) level. Like spiro-cyclohexane analogs, they were shown to have a non-chair conformation.