2,2-二甲基-4,5-二乙烯基-1,3-二氧戊环 | 4362-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,2-二甲基-4,5-二乙烯基-1,3-二氧戊环
• 中文别名: N-氨基甲酰-5-O-磷羧基-β-D-呋喃核糖基胺
• 英文名称: 2,2-dimethyl-4,5-divinyl-1,3-dioxolane
• 英文别名: 2,2-dimethyl-4,5-divinyl-[1,3]dioxolane；1,3-Dioxolane, 2,2-dimethyl-4,5-divinyl-；4,5-bis(ethenyl)-2,2-dimethyl-1,3-dioxolane
• CAS: 4362-67-8
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: OLWFHQUMBKPUNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  2,2-二甲基-4,5-二乙烯基-1,3-二氧戊环 在 硫脲 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 3,4-dihydroxy-1,2-epithio-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
• 作为产物：
  描述：

  2,2-dimethyl-4,5-di(2-oxiranyl)-1,3-dioxolane 生成 2,2-二甲基-4,5-二乙烯基-1,3-二氧戊环
  参考文献：
  名称：

  SCHOBERT, RAINER;HOHLEIN, UDO, SYNLETT,(1990) N, C. 465-466

  摘要：

  DOI：

文献信息

• Synthesis, Reactions, and Structural Studies of Two-Carbon Bridged Spiropentanes
  作者：Kenneth B. Wiberg、John R. Snoonian

  DOI：10.1021/jo970972y

  日期：1998.3.1

  The syntheses of three 4,5-disubstituted derivatives of tricyclo[4.1.0.0(1,3)]heptane (3) are reported. The relative stereochemistry of the oxygen substituents in these compounds was deduced by C-13 NMR spectroscopy and unequivocally confirmed by single-crystal X-ray analysis of the thiocarbonate derivative 15, The experimental results obtained from reaction of the 2,4-diol 6 under Swern conditions and with TPAP were explained by the results of ab initio calculations at the MP2/6-31G* level of theory.
• Synthesis, Chromatographic Separation, Vibrational Circular Dichroism Spectroscopy, and ab Initio DFT Studies of Chiral Thiepane Tetraol Derivatives
  作者：Vanda Cerè、Francesca Peri、Salvatore Pollicino、Alfredo Ricci、Frank J. Devlin、Philip J. Stephens、Francesco Gasparrini、Romina Rompietti、Claudio Villani

  DOI：10.1021/jo048629y

  日期：2005.1.1

  Optically pure enantiomers of the chiral tetrahydroxythiepane derivative 3,6-dihydroxy-4,5-O-isopropylidene-thiepane (3) are obtained using a novel protocol in which a library of all possible stereoisomers of 3 is synthesized, followed by two-step stereoselective chromatography, using, first, conventional achiral and, then, chiral stationary phases. Configurational and conformational analysis of 3 are carried out using Vibrational Circular Dichroism (VCD) spectroscopy in conjunction with ab initio DFT calculations. The absolute configuration of 3 is shown to be 3R,4S,5R,6R-(+)/ 3S,4R,5S,6S-(-).
• Synthesis of Cycloalkanones from Dienes and Allylamines through CbH and CbC Bond Activation Catalyzed by a Rhodium(I) Complex This work was supported by the National Research Laboratory Program (2000-N-NL-01-C-271) administered by Ministry of Science and Technology, and by the Korean Science and Engineering Foundation (20004010).
  作者：Dae-Yon Lee、In-Jung Kim、Chul-Ho Jun

  DOI：10.1002/1521-3773(20020816)41:16<3031::aid-anie3031>3.0.co;2-x

  日期：2002.8.16
• 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.
• SCHOBERT, RAINER;HOHLEIN, UDO, SYNLETT,(1990) N, C. 465-466
  作者：SCHOBERT, RAINER、HOHLEIN, UDO

  DOI：——

  日期：——